Pentacyclic triterpenoid c-glycoside, method for producing and use of the same

Abstract

To provide pentacyclic triterpenoid C-glycoside, a method for producing the glycoside, and use of the glycoside.SOLUTION: Provided is a compound expressed by formula I. The compound can be used for producing a drug for treating metabolic diseases such as diabetes mellitus, and viral diseases caused by an influenza virus or a coronavirus.SELECTED DRAWING: None

Description

[Technical Field]

[0001] The present invention relates to the field of medicinal chemistry and medicine, and more particularly to pentacyclic triterpenoid C-glycosides, their preparation methods, and their use in the manufacture of drugs for the treatment of metabolic diseases and antiviral effects, particularly for the treatment of diseases such as diabetes, influenza, and pneumonia caused by coronaviruses. [Background technology]

[0002] Diabetes mellitus (DM) is a chronic, systemic metabolic disease resulting from the long-term interaction of genetic and environmental factors. It is characterized by elevated plasma glucose levels and disrupts normal physiological functions due to impaired glucose, fat, and protein metabolism, primarily due to insufficient or impaired insulin secretion or action (insulin resistance). Diabetic complications can be divided into acute and chronic complications. Acute complications include diabetic ketoacidosis, hyperglycemic hyperosmolar syndrome, various acute infections, and lactic acidosis. Hypoglycemia, which occurs during diabetes treatment, is also one of the most common acute complications. Chronic complications include diabetic eye disease, diabetic nephropathy, diabetic neuropathy, diabetic cardiovascular disease, diabetic foot disease, and diabetic skin disease. Major clinical manifestations of diabetes include polydipsia, polyuria, polyphagia, and weight loss.

[0003] Diabetes mellitus (IDDM) is divided into insulin-dependent diabetes mellitus (type 1 diabetes) and non-insulin-dependent diabetes mellitus (NIDDM), accounting for more than 90% of diabetic patients. The exact etiology and pathogenesis of type 1 diabetes are still unclear. Its etiology is a combination of genetic and environmental factors, primarily due to damage to pancreatic islet B cells in vivo, which prevents the body from producing insulin. Patients must administer daily insulin injections to control their blood insulin levels. Type 2 diabetes is a form of metabolic syndrome characterized by inability to control blood glucose levels in vivo. It is primarily characterized by hyperglycemia, insulin resistance, and insufficient insulin secretion. The pathogenesis of type 2 diabetes is primarily due to insulin resistance, which prevents the body from effectively utilizing insulin, or reduced insulin secretion, which prevents the body from meeting its needs. Because such diabetic patients are able to secrete insulin, insulin therapy is generally not required; blood glucose can be controlled solely through dietary modification and oral hypoglycemic drugs.

[0004] Pentacyclic triterpenoids are secondary plant metabolites found in various plant organs, with some species occupying up to 30% of the plant's dry weight. Although the molecular mechanism remains unclear, triterpenoids are generally recognized as an important component of plant defense systems against pathogens and herbivores. Several glycosidic pentacyclic triterpenoids have been reported to have in vitro anti-influenza virus activity comparable to or even greater than that of oseltamivir. Mechanistic studies have shown that these compounds bind tightly to the hemagglutinin (HA) protein, disrupting the interaction between hemagglutinin and sialic acid receptors and blocking virus entry into host cells, a process that is unlikely to result in drug resistance. Furthermore, one study showed that pentacyclic triterpenoids can bind to the coronavirus N protein, inhibiting virus assembly and achieving anti-coronavirus activity. Furthermore, because the coronavirus N protein is highly conserved and plays an important role in immunity, compounds targeting the N protein are promising antiviral small molecule compounds.

[0005] Among sugar drugs, O-glycosides and N-glycosides are easily oxidized and metabolized in the body, while C-glycosides exhibit good metabolic stability both in vivo and in vitro, which has attracted widespread attention from scientists. Therefore, pentacyclic triterpenoid C-glycosides have a very bright future in the research and development of hypoglycemic and antiviral drugs. For these reasons, the development of novel pentacyclic triterpenoid C-glycosides is urgently needed in this field. Summary of the Invention [Problem to be solved by the invention]

[0006] The object of the present invention is to provide a pentacyclic triterpene C-glycoside derivative compound represented by general formula I, or a pharmaceutically acceptable salt, racemate, R-isomer, S-isomer, or mixture thereof: [Means for solving the problem]

[0007] A first aspect of the present invention provides a pentacyclic triterpene C-glycoside derivative compound having a structure represented by the following general formula I, or its racemate, R-isomer, S-isomer, pharmaceutically acceptable salt, or mixture thereof: [ka] During the ceremony, Ring A is selected from the group consisting of a 6-membered saturated or unsaturated carbocyclic ring; R1, R2, and R3 are each independently selected from the group consisting of hydrogen and methyl; R4 is selected from the group consisting of hydrogen and isopropenyl; R5 is hydrogen, deuterium, tritium, halogen, cyano, amino, nitro, hydroxyl, sulfydryl, aldehyde group, carboxyl, sulfonyl, phosphate group, substituted or unsubstituted C1-C6 alkyl, substituted or unsubstituted C1-C6 alkoxy, substituted or unsubstituted C6-C 10 aryl, substituted or unsubstituted 5- to 7-membered heterocycle having 1 to 3 heteroatoms selected from oxygen, sulfur, and nitrogen, substituted or unsubstituted C1-C6 alkyl-phenyl, substituted or unsubstituted C3-C 12 Cycloalkyl, substituted or unsubstituted C2-C 10 Acyl, substituted or unsubstituted C2-C 10 Ester group, substituted or unsubstituted C6-C 10 selected from the group consisting of aryloxy, substituted or unsubstituted C1-C6 amido, or Y-R7; Y is -(CH2) m selected from the group consisting of CHR9-, carbonyl, -CONH, and COO-; where m is 0 or 1, R7 is hydrogen, substituted or unsubstituted C1-C6 alkyl, substituted or unsubstituted C2-C6 alkenyl, substituted or unsubstituted 5- to 7-membered heterocycle having 1 to 3 heteroatoms selected from oxygen, sulfur, and nitrogen, substituted or unsubstituted C2-C 10 selected from the group consisting of an ester group, a substituted or unsubstituted C5-C9 furanosyl, and a substituted or unsubstituted C5-C9 pyranosyl; Z is selected from the group consisting of carbonyl, CH(R9)2, C=N-R8, C=N-NH-R8, or -X-R6; R8 is selected from the group consisting of hydrogen, deuterium, tritium, halogen, cyano, amino, nitro, hydroxy, sulfhydryl, an aldehyde group, carboxy, sulfonyl, substituted or unsubstituted C1-C6 alkyl, substituted or unsubstituted C1-C6 alkoxy, substituted or unsubstituted C6-C10 aryl, a substituted or unsubstituted 5-7 membered heterocycle having 1-3 heteroatoms selected from oxygen, sulfur, and nitrogen, a substituted or unsubstituted C1-C6 alkyl-phenyl, a substituted or unsubstituted C3-C12 cycloalkyl, a substituted or unsubstituted C2-C10 acyl, a substituted or unsubstituted C2-C10 ester group, a substituted or unsubstituted C6-C10 aryloxy, and a substituted or unsubstituted C1-C6 amide; R9 is selected from the group consisting of hydrogen, deuterium, tritium, halogen, cyano, amino, nitro, hydroxy, and sulfhydryl; R6 is selected from the group consisting of hydrogen, substituted or unsubstituted C1-C6 alkyl, substituted or unsubstituted C2-C6 alkenyl, substituted or unsubstituted 5-7 membered heterocycle having 1-3 heteroatoms selected from oxygen, sulfur and nitrogen, substituted or unsubstituted C5-C9 furanosyl, substituted or unsubstituted C5-C9 pyranosyl, and the substitution means that one or more hydrogens or hydroxyl groups on the sugar ring are replaced with hydrogen, deuterium, tritium, halogen, cyano, amino, nitro, sulfhydryl, aldehyde group, carboxy, benzyl, substituted or unsubstituted C1-C 12 Alkoxycarbonyl, substituted or unsubstituted C2-C 12 Alkylaminocarbonyl, substituted or unsubstituted C2-C 10 It means that it is substituted with a substituent selected from the group consisting of acyl, sulfonyl, phosphoryl, C5-C9 furanosyl, and C5-C9 pyranosyl; X is selected from the group consisting of -CHR9-, carbonyl, S, -NHC(O)-R8, -NHS(O)2-R8, -NHC(O)NH-R8, -NHC(S)NH-R8, -COO-, -OS(O)2-R8; n is 1 or 2, Unless otherwise specified, in the above formula, the substitution means that a hydrogen atom on the corresponding group or a hydroxy on the sugar ring is replaced with a deuterium, tritium, halogen, hydroxy, carboxy, sulfhydryl, benzyl, C1-C 12 Alkoxycarbonyl, C1-C6 aldehyde group, amino, C1-C6 amide, nitro, cyano, unsubstituted or halogenated C1-C6 alkyl, C2-C 10 Alkenyl, C1-C6 alkoxy, C1-C6 alkyl-amine group, C6-C 10 Aryl, 5- or 6-membered heteroaryl, 5- or 6-membered non-aromatic heterocyclic group, —O—(C6-C 10 aryl), —O—(5- or 6-membered heteroaryl), C1-C 12 Alkylaminocarbonyl, substituted or unsubstituted C2-C 10 It means that it is substituted with one or more substituents selected from the group consisting of acyl, sulfonyl (-SO2-OH), phosphoryl (-PO3-OH), C5 to C9 furanosyl, and C5 to C9 pyranosyl.

[0008] In another preferred embodiment, the compound of formula I has a structure represented by general formula II: [ka] During the ceremony, R5 is hydrogen, deuterium, tritium, halogen, cyano, amino, nitro, hydroxy, sulfhydryl, an aldehyde group, carboxy, sulfonyl, a phosphate group, a substituted or unsubstituted C1-C6 alkyl, a substituted or unsubstituted C1-C6 alkoxy, a substituted or unsubstituted C6-C10 aryl, a substituted or unsubstituted 5- to 7-membered heterocycle having 1 to 3 heteroatoms selected from oxygen, sulfur, and nitrogen, a substituted or unsubstituted C1-C6 alkyl-phenyl, a substituted or unsubstituted C3-C12 cycloalkyl, a substituted or unsubstituted C2-C10 acyl, a substituted or unsubstituted C2-C 10 selected from the group consisting of an ester group, a substituted or unsubstituted C6-C10 aryloxy, and a substituted or unsubstituted C1-C6 amide; X is selected from the group consisting of -CHR9-, carbonyl; R6 is selected from the group consisting of substituted or unsubstituted C5-C9 furanosyl and substituted or unsubstituted C5-C9 pyranosyl, and the substitution means that one or more hydrogens or hydroxyls on the sugar ring are substituted with a substituent selected from the group consisting of hydrogen, deuterium, tritium, halogen, cyano, amino, nitro, sulfhydryl, aldehyde group, carboxy, benzyl, substituted or unsubstituted C1-C12 alkoxycarbonyl, substituted or unsubstituted C2-C12 alkylaminocarbonyl, substituted or unsubstituted C2-C10 acyl, sulfonyl, phosphoryl, C5-C9 furanosyl, and C5-C9 pyranosyl; R9 is selected from the group consisting of hydrogen, deuterium, tritium, halogen, cyano, amino, nitro, hydroxy, and sulfhydryl; Ring A is selected from the group consisting of a 6-membered saturated or unsaturated carbocyclic ring; n is 1 or 2.

[0009] In another preferred embodiment, the compound of formula I has a structure represented by general formula III: [ka] During the ceremony, R1, R2, and R3 are each independently selected from the group consisting of hydrogen and methyl; R4 is selected from the group consisting of hydrogen and isopropenyl; R7 is selected from the group consisting of hydrogen, substituted or unsubstituted C5-C9 furanosyl, and substituted or unsubstituted C5-C9 pyranosyl, and the substitution means that one or more hydrogens or hydroxyls on the sugar ring are substituted with a substituent selected from the group consisting of hydrogen, deuterium, tritium, halogen, cyano, amino, nitro, sulfhydryl, aldehyde group, carboxy, benzyl, substituted or unsubstituted C1-C12 alkoxycarbonyl, substituted or unsubstituted C1-C12 alkylaminocarbonyl, substituted or unsubstituted C2-C10 acyl, sulfonyl, phosphoryl, C5-C9 furanosyl, and C5-C9 pyranosyl; Y is -(CH2)m CHR9-, carbonyl; m is 0 or 1, R9 is selected from the group consisting of hydrogen, deuterium, tritium, halogen, cyano, amino, nitro, hydroxy, and sulfhydryl; Z is selected from the group consisting of carbonyl, CH(R9)2, =N-R8, and -X-R6; R9 is selected from the group consisting of hydrogen, halogen, cyano, amino, nitro, hydroxy, and sulfhydryl; X is selected from the group consisting of -CHR9-, carbonyl, S, -NHC(O)-R8, -NHS(O)2-R8, -NHC(O)NH-R8, -NHC(S)NH-R8, -COO-, -OS(O)2-R8; R6 is selected from the group consisting of hydrogen, substituted or unsubstituted C1-C6 alkyl, substituted or unsubstituted C2-C6 alkenyl, substituted or unsubstituted 5-7 membered heterocycle having 1-3 heteroatoms selected from oxygen, sulfur and nitrogen, substituted or unsubstituted C5-C9 furanosyl, substituted or unsubstituted C5-C9 pyranosyl, and the substitution means that one or more hydrogens or hydroxyl groups on the sugar ring are replaced with hydrogen, deuterium, tritium, halogen, cyano, amino, nitro, sulfhydryl, aldehyde group, carboxy, benzyl, substituted or unsubstituted C1-C 12 Alkoxycarbonyl, substituted or unsubstituted C2-C 12 Alkylaminocarbonyl, substituted or unsubstituted C2-C 10 It means that the substituent is selected from the group consisting of acyl, sulfonyl, phosphoryl, C5-C9 furanosyl, and C5-C9 pyranosyl; Ring A is selected from the group consisting of a 6-membered saturated or unsaturated carbocyclic ring; n is 1 or 2.

[0010] In another preferred embodiment, the compound of formula I has a structure represented by the following general formula IV, V or VI: [ka]

[0011] In another preferred example, R5 is hydrogen, halogen, hydroxy, carboxy, substituted or unsubstituted C1 to C6 alkyl, substituted or unsubstituted C1 to C6 alkoxy, substituted or unsubstituted C2 to C10 acyl, substituted or unsubstituted C2 to C 10 It is selected from the group consisting of an ester group, and a substituted or unsubstituted C1 to C6 amide.

[0012] In another preferred example, R9 is selected from the group consisting of hydrogen, hydroxy, aldehyde, sulfhydryl, or -X-R6; X is selected from the group consisting of -CHR9-, carbonyl, S, -NHC(O)-R8, -NHS(O)2-R8, -NHC(O)NH-R8, -NHC(S)NH-R8, -COO-, -OS(O)2-R8; R6 is selected from the group consisting of substituted or unsubstituted C1-C6 alkyl, substituted or unsubstituted C2-C6 alkenyl, substituted or unsubstituted 5-7 membered heterocycle having 1-3 heteroatoms selected from oxygen, sulfur and nitrogen, substituted or unsubstituted C5-C9 furanosyl, substituted or unsubstituted C5-C9 pyranosyl, and the substitution means that one or more hydrogens or hydroxyl groups on the sugar ring are replaced with hydrogen, deuterium, tritium, halogen, cyano, amino, nitro, sulfhydryl, aldehyde group, carboxy, benzyl, substituted or unsubstituted C1-C 12 Alkoxycarbonyl, substituted or unsubstituted C2-C 12 Alkylaminocarbonyl, substituted or unsubstituted C2-C 10 It means that it is substituted with a substituent selected from the group consisting of acyl, sulfonyl, phosphoryl, C5-C9 furanosyl, and C5-C9 pyranosyl.

[0013] In another preferred embodiment, the pentacyclic triterpenoid C-glycoside is any of the compounds in the examples.

[0014] A second aspect of the present invention provides a method for producing the compound according to the first aspect of the present invention, characterized by including the following Scheme 1 or Scheme 2: Scheme 1: Starting from a compound of formula IIa, a compound of formula II is produced through step a and optional step b, c or d. [ka] wherein the definitions of each group are as defined in the first aspect of the present invention; Step a: reacting compound IV with compound III to obtain the product of step a; Step b: reducing the product of step a to obtain the product of step b; Step c: alkylating the product of step b to obtain the product of step c; Step d: reacting the product of step c with a Dess-Martin reagent to obtain a compound of formula II; wherein the structure of compound IV is: [ka]

[0015] Scheme 2: A compound of formula III is produced from a compound of formula IIIa through step a and optional step b, c or d. [ka]

[0016] A third aspect of the present invention provides a pharmaceutical composition comprising a therapeutically effective amount of one or more of the compounds of formula I according to the first aspect of the invention, pharmaceutically acceptable salts, racemates, R-isomers and S-isomers thereof, and one or more pharmaceutically acceptable carriers, excipients, adjuvants, auxiliary materials and / or diluents.

[0017] A fourth aspect of the present invention provides the use of a compound of formula I or a compound of formula II, or a racemate, R-isomer, S-isomer or a pharmaceutically acceptable salt thereof, according to the first aspect of the present invention, in the manufacture of a medicament for treating or preventing metabolic and viral diseases associated with diabetes, preferably wherein the disease is selected from the group consisting of diabetes, influenza, obesity, liver fibrosis, metabolic diseases and viral diseases.

[0018] It should be noted that within the scope of the present invention, the above-mentioned technical features of the present invention and the technical features specifically described below (e.g., in the Examples) can be combined with each other to form new or preferred technical schemes, which will not be described here due to space limitations. [Brief explanation of the drawings]

[0019] [Figure 1] The OGTT experimental data of ICR mice A2, A4, A6, A10, A25, A43, A44, A47 and A67 are shown. [Figure 2] This shows that A25 and A43 exhibit excellent hypoglycemic effects in vivo. [Figure 3] EC50 and in vitro GLP secretion promoting effect of A64 and the positive drug ANT777 are shown.

[0020] [Figure 4] The compounds of the present invention exhibit a virus inhibition rate and low cytotoxicity equivalent to those of ribavirin, an active drug, and show that the compounds have a virus inhibition rate close to that of ribavirin, an active drug, but lower cytotoxicity than ribavirin. [Figure 5] Data from affinity experiments of A102, A104, A106, A108, A112, A114, A116, A117, A120, A121, A122, A123, A124, A125, A126, and A127 with SARS-Cov-2 N protein are shown.

[0021] [Figure 6-1]1 shows data from an affinity experiment between compounds A102, A114, and A116 and N protein. [Figure 6-2] 1 shows data from an experiment on the affinity of compounds A102, A114, and A116 with N protein. [Figure 7] Data from experiments in which A102, A104, A114, A117, A118, A119, A120, A121, A122, A123, A124, A125, A126, A127, A128, and A129 inhibit SARS-Cov-2 virus copying are shown. [Figure 8] Data from experiments in which A102, A104, A114, A117, A118, A119, A120, A121, A122, A123, A124, A125, A126, A127, A128, and A129 inhibit SARS-Cov-2 virus copying are shown. [Figure 9] The A104 compound exhibits good PK properties in mice. [Figure 10] The A104 compound exhibits good PK properties in mice. DETAILED DESCRIPTION OF THE INVENTION

[0022] As a result of extensive and intensive research, the present inventors have unexpectedly discovered, for the first time, a pentacyclic triterpene C-glycoside with a novel structure and excellent performance that has oral hypoglycemic or antiviral activity, and have completed the present invention based on this discovery.

[0023] term In the present invention, the halogen is F, Cl, Br or I. In the present invention, unless otherwise specified, the terms used have the general meanings known to those skilled in the art.

[0024] In the present invention, the term "C1-C6 alkyl" refers to a straight or branched alkyl having 1 to 6 carbon atoms, including, but not limited to, methyl, ethyl, propyl, isopropyl, butyl, isobutyl, s-butyl, t-butyl, pentyl, and hexyl, and preferably ethyl, propyl, isopropyl, butyl, isobutyl, s-butyl, and t-butyl.

[0025] In the present invention, the term "C1-C6 alkoxy" refers to a straight or branched chain alkoxy having 1 to 6 carbon atoms, including, but not limited to, methoxy, ethoxy, propoxy, isopropoxy, and butoxy.

[0026] In the present invention, the term "C2-C6 alkenyl" refers to a straight-chain or branched alkenyl containing one double bond and having 2 to 6 carbon atoms, and includes, but is not limited to, vinyl, propenyl, butenyl, isobutenyl, pentenyl, and hexenyl.

[0027] In the present invention, the term "C2-C6 alkynyl" refers to a straight or branched alkynyl containing one triple bond and having 2 to 6 carbon atoms, including, but not limited to, ethynyl, propynyl, butynyl, isobutynyl, pentynyl, and hexynyl.

[0028] In the present invention, the term "C3-C10 cycloalkyl" refers to a cyclic alkyl having 3 to 10 carbon atoms on the ring, including, but not limited to, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, and cyclodecyl. The terms "C3-C8 cycloalkyl," "C3-C7 cycloalkyl," and "C3-C6 cycloalkyl" have similar meanings.

[0029] As used herein, the term "C3-C10 cycloalkenyl" refers to a cyclic alkenyl having 3 to 10 carbon atoms on the ring, including, but not limited to, cyclopropenyl, cyclobutenyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, cyclooctenyl, and cyclodecenyl. The term "C3-C7 cycloalkenyl" has an analogous meaning.

[0030] As used herein, the term "C1-C12 alkoxycarbonyl" refers to an alkoxycarbonyl having 1 to 12 carbon atoms on the alkyl chain, including, but not limited to, methoxycarbonyl, ethoxycarbonyl, propoxycarbonyl, isopropoxycarbonyl, tert-butoxycarbonyl, benzyloxycarbonyl, and the like.

[0031] As used herein, the term "C1-C12 alkylaminocarbonyl" refers to an alkylaminocarbonyl having 1 to 12 carbon atoms in the alkyl chain, including, but not limited to, methylaminocarbonyl, ethylaminocarbonyl, propylaminocarbonyl, isopropylaminocarbonyl, tert-butylaminocarbonyl, benzylaminocarbonyl, dimethylaminocarbonyl, and the like.

[0032] In the present invention, the term "C5-C9 furanosyl" refers to a furanosyl having 5 to 9 carbon atoms in which the 1-position of the glycosyl is linked to the main chain, and includes, but is not limited to, ribofuranosyl, deoxyribofuranosyl, galactofuranosyl, etc.

[0033] In the present invention, the term "C5-C9 pyranosyl" refers to a pyranosyl having 5 to 9 carbon atoms in which the 1-position of the glycosyl is linked to the main chain, and includes, but is not limited to, glucopyranosyl, glucopyranuronosyl, rhamnopyranosyl, galactopyranosyl, mannopyranosyl, xylopyranosyl, etc.

[0034] In the present invention, the terms "aromatic ring" or "aryl" have the same meaning, and preferably "aryl" is "C6-C12 aryl" or "C6-C10 aryl". The term "C6-C12 aryl" refers to an aromatic ring group having 6 to 12 carbon atoms and no heteroatoms in the ring, such as phenyl, naphthyl, etc. The term "C6-C10 aryl" has a similar meaning.

[0035] In the present invention, the terms "aromatic heterocycle" and "heteroaryl" have the same meaning and refer to a heteroaromatic group containing one or more heteroatoms. Heteroatoms in this context include oxygen, sulfur, and nitrogen. Examples include furyl, thienyl, pyridyl, pyrazolyl, pyrrolyl, N-alkylpyrrolyl, pyrimidinyl, pyrazinyl, imidazolyl, and tetrazolyl. The heteroaryl ring may be fused to an aryl, heterocyclic, or cycloalkyl ring, where the ring connected to the parent structure is a heteroaryl ring. The heteroaryl may be substituted or unsubstituted.

[0036] In the present invention, the term "3- to 12-membered heterocyclic group" refers to a saturated or unsaturated 3- to 12-membered ring group containing 1 to 3 heteroatoms selected from oxygen, sulfur, and nitrogen on the ring, such as dioxolyl. The term "3- to 7-membered heterocyclic group" has a similar meaning.

[0037] In the present invention, the term "substituted" means that one or more hydrogen atoms on a specific group are replaced with a specific substituent. The specific substituents are those in the corresponding descriptions above or in each example. Unless otherwise specified, a substituent may have one substituent selected from a specific group at any substitutable position of the group, and the substituents may be the same or different at each position. A cyclic substituent, such as a heterocyclic alkyl, may be linked to another ring, such as a cycloalkyl, to form a spiro-bicyclic ring system, for example, the two rings share one carbon atom. As can be understood by those skilled in the art, the desired combination of substituents in the present invention may be a stable or chemically feasible combination. Examples of the substituent include, but are not limited to, C alkyl, C alkenyl, C alkynyl, C cycloalkyl, 3- to 12-membered heterocyclic group, aryl, heteroaryl, halogen, hydroxy, carboxy (—COOH), C aldehyde, C acyl, C ester group, C alkoxycarbonyl, amino, alkoxy, and C sulfonyl.

[0038] Pentacyclic triterpenoid C-glycosides The present invention provides a pentacyclic triterpene C-glycoside derivative compound having a structure represented by the following general formula I or II, or its racemate, R-isomer, S-isomer, pharmaceutically acceptable salt, or a mixture thereof: [ka] During the ceremony, R1, R2, and R3 are each independently selected from the group consisting of hydrogen and methyl; R4 is selected from the group consisting of hydrogen and isopropenyl; R5 is selected from the group consisting of hydrogen, deuterium, tritium, halogen, cyano, amino, nitro, hydroxy, sulfhydryl, an aldehyde group, carboxy, sulfonyl, a phosphate group, a substituted or unsubstituted C1-C6 alkyl, a substituted or unsubstituted C1-C6 alkoxy, a substituted or unsubstituted C6-C10 aryl, a substituted or unsubstituted 5-7 membered heterocycle containing 1-3 heteroatoms selected from oxygen, sulfur, and nitrogen, a substituted or unsubstituted C1-C6 alkyl-phenyl, a substituted or unsubstituted C3-C12 cycloalkyl, a substituted or unsubstituted C2-C10 acyl, a substituted or unsubstituted C2-C10 ester group, a substituted or unsubstituted C6-C10 aryloxy, and a substituted or unsubstituted C1-C6 amide; R6 is selected from the group consisting of substituted or unsubstituted C5-C9 furanosyl and substituted or unsubstituted C5-C9 pyranosyl, and the substitution means that one or more hydrogens or hydroxyls on the sugar ring are substituted with a substituent selected from the group consisting of hydrogen, deuterium, tritium, halogen, cyano, amino, nitro, sulfhydryl, aldehyde group, carboxy, benzyl, substituted or unsubstituted C1-C12 alkoxycarbonyl, substituted or unsubstituted C1-C12 alkylaminocarbonyl, substituted or unsubstituted C2-C10 acyl, sulfonyl, phosphoryl, C5-C9 furanosyl, and C5-C9 pyranosyl; X is selected from the group consisting of -CHR9-, carbonyl; R9 is selected from the group consisting of hydrogen, deuterium, tritium, halogen, cyano, amino, nitro, hydroxy, and sulfhydryl; Ring A is selected from the group consisting of a 6-membered saturated or unsaturated carbocyclic ring; n is 1 or 2.

[0039] [ka] During the ceremony, R1, R2, and R3 are each independently selected from the group consisting of hydrogen and methyl; R4 is selected from the group consisting of hydrogen and isopropenyl; R7 is selected from the group consisting of substituted or unsubstituted C5-C9 furanosyl and substituted or unsubstituted C5-C9 pyranosyl, and the substitution means that one or more hydrogens or hydroxyls on the sugar ring are substituted with a substituent selected from the group consisting of hydrogen, deuterium, tritium, halogen, cyano, amino, nitro, sulfhydryl, aldehyde group, carboxy, benzyl, substituted or unsubstituted C1-C12 alkoxycarbonyl, substituted or unsubstituted C1-C12 alkylaminocarbonyl, substituted or unsubstituted C2-C10 acyl, sulfonyl, phosphoryl, C5-C9 furanosyl, and C5-C9 pyranosyl; Y is selected from the group consisting of —(CH2)mCHR9—, carbonyl; m is 0 or 1.

[0040] R9 is selected from the group consisting of hydrogen, deuterium, tritium, halogen, cyano, amino, nitro, hydroxy, and sulfhydryl; Z is selected from the group consisting of carbonyl -CH(R)-, =N-R; R8 is selected from the group consisting of hydrogen, deuterium, tritium, halogen, cyano, amino, nitro, hydroxy, sulfhydryl, an aldehyde group, carboxy, sulfonyl, substituted or unsubstituted C1-C6 alkyl, substituted or unsubstituted C1-C6 alkoxy, substituted or unsubstituted C6-C10 aryl, a substituted or unsubstituted 5-7 membered heterocycle containing 1-3 heteroatoms selected from oxygen, sulfur, and nitrogen, a substituted or unsubstituted C1-C6 alkyl-phenyl, a substituted or unsubstituted C3-C12 cycloalkyl, a substituted or unsubstituted C2-C10 acyl, a substituted or unsubstituted C2-C10 ester group, a substituted or unsubstituted C6-C10 aryloxy, and a substituted or unsubstituted C1-C6 amide; Ring A is selected from the group consisting of a 6-membered saturated or unsaturated carbocyclic ring; n is 1 or 2.

[0041] In a more preferred implementation scheme of the present invention, the compounds of general formula I and general formula II of the present invention are preferably the following specific compounds. [Table 1-1] Table 1-2 Table 1-3 Table 1-4 Table 1-5 Table 1-6 Table 1-7 Table 1-8 Table 1-9 Table 1-10 Table 1-11 Table 1-12 Table 1-13 Table 1-14 Table 1-15 Table 1-16 Table 1-17 Table 1-18 Table 1-19 Table 1-20 Table 1-21 Table 1-22 Table 1-23 Table 1-24 Table 1-25 Table 1-26 Table 1-27 Table 1-28 Table 1-29 Table 1-30 Table 1-31 Table 1-32 Table 1-33 Table 1-34 [Table 1-35] [Table 1-36] [Table 1-37] [Table 1-38] [Table 1-39] [Table 1-40] [Table 1-41] [Table 1-42] [Table 1-43] [Table 1-44] [Table 1-45]

[0042] Active ingredient The compound of the present invention may be an acrylic acid derivative compound having a structure represented by the following general formula I, or its racemate, R-isomer, S-isomer, pharmaceutically acceptable salt, or a mixture thereof. [ka]

[0043] The definitions of each group are as described above. The compounds of the present invention have an asymmetric center, a chiral axis and a chiral plane and may exist in the form of racemates, R-isomers or S-isomers. Those skilled in the art can resolve the racemates to obtain the R-isomers and / or S-isomers by conventional techniques.

[0044] The present invention provides pharmaceutically acceptable salts of the compounds of general formula I and general formula II, specifically, conventional pharmaceutically acceptable salts formed by reaction of the compounds of general formula I and general formula II with an inorganic or organic acid. For example, common pharmaceutically acceptable salts may be prepared by reacting the compounds of Formula I and Formula II with an inorganic or organic acid, and the inorganic acids include hydrochloric acid, hydrobromic acid, sulfuric acid, nitric acid, sulfamic acid, and phosphoric acid. The organic acids include citric acid, tartaric acid, lactic acid, pyruvic acid, acetic acid, benzenesulfonic acid, p-toluenesulfonic acid, methanesulfonic acid, naphthalenesulfonic acid, ethanesulfonic acid, naphthalenedisulfonic acid, maleic acid, malic acid, malonic acid, fumaric acid, succinic acid, propionic acid, oxalic acid, trifluoroacetic acid, stearic acid, pamoic acid, hydroxymaleic acid, phenylacetic acid, and the like. or common pharmaceutically acceptable salts are sodium, potassium, calcium, aluminum or ammonium salts formed by the compounds of general formula I and general formula II with inorganic alkali; or methylamine, ethylamine or ethanolamine salts formed by the compounds of general formula I and general formula II with organic alkali.

[0045] Manufacturing method Another aspect of the present invention provides a method for preparing compounds represented by general formula I and general formula II, which can be carried out according to the following Scheme 1 and Scheme 2.

[0046] Compounds of formula (I) may be prepared by the method shown in Scheme 1 below. The structural formulas and symbols for R groups used in the following schemes are used only in this section. Compounds of formula (III), (IV) and (V) may be commercially available or may be synthesized by techniques common in the art.

[0047] Scheme 1: [ka] The definitions of each group are the same as above.

[0048] Step a: Compound IV and Compound III were added to a 0.1 mol / L solution of samarium diiodide in redistilled tetrahydrofuran at 0° C., and reacted for 1 hour under argon protection. Step b: The product of the previous step was dissolved in a mixed solvent of ethyl acetate:methanol (1:1), Pd / C was added, and the mixture was reacted at 50° C. for 12 hours under a hydrogen gas atmosphere.

[0049] Step c: After dissolving the product from the previous step in CS₂, add NaH (60% oil mixture) and stir at room temperature for 2 hours. Next, add CH₃I and let it react overnight. After purifying by column chromatography, dissolve it in ultra-dehydrated toluene, add AIBN and tri-n-butyltin hydride while stirring, and stir at reflux for 4 hours. Step d: Dissolve the product from the previous step in dichloromethane, add Dess-Martin reagent, and stir for 2 h.

[0050] The structure of compound IV is as follows: [ka]

[0051] Scheme 2: [ka] The definitions of each group are the same as above. Steps a, b, c, and d are defined as in Scheme 1.

[0052] Pharmaceutical compositions and methods of administration The compounds of the present invention have excellent hypoglycemic activity and influenza virus inhibitory activity, and therefore the compounds of the present invention and their various crystalline forms, pharmaceutically acceptable inorganic or organic salts, hydrates or solvates, as well as pharmaceutical compositions containing the compounds of the present invention as a main active ingredient, can be used for the treatment, prevention and alleviation of elevated blood sugar levels and related diseases caused by influenza viruses.

[0053] The pharmaceutical composition of the present invention contains a compound of the present invention or a pharmaceutically acceptable salt thereof and a pharmaceutically acceptable excipient or carrier in a safe and effective amount. Here, "safe and effective amount" refers to an amount of the compound sufficient to clearly improve the condition but without causing serious side effects. Generally, the pharmaceutical composition contains 1 to 2000 mg, more preferably 5 to 200 mg, of the compound / drug of the present invention. Preferably, the "one agent" is one capsule or tablet.

[0054] The term "pharmaceutically acceptable carrier" refers to one or more compatible solid or liquid fillers or gel-like substances that must be of sufficient purity and sufficiently low toxicity to be suitable for human use. "Compatibility" means that each component in the composition can be mixed with the compound of the present invention and that they can be mutually mixed without significantly reducing the efficacy of the compound. Examples of pharmaceutically acceptable carrier moieties include cellulose and its derivatives (e.g., sodium carboxymethyl cellulose, sodium ethyl cellulose, cellulose acetate, etc.), gelatin, talc, solid lubricants (e.g., stearic acid, magnesium stearate, etc.), calcium sulfate, vegetable oils (e.g., soybean oil, sesame oil, peanut oil, olive oil, etc.), polyols (e.g., propylene glycol, glycerin, mannitol, sorbitol, etc.), emulsifiers (e.g., Twen®), wetting agents (e.g., sodium dodecyl sulfate, etc.), colorants, flavoring agents, stabilizers, antioxidants, preservatives, and heat-free raw water.

[0055] The method of administration of the compound or pharmaceutical composition of the present invention is not particularly limited, and representative administration methods include, but are not limited to, oral administration, intratumoral administration, rectal administration, parenteral administration (intravenous administration, intramuscular administration, or subcutaneous administration), and topical administration.

[0056] Solid dosage forms for oral administration include capsules, tablets, pills, powders, and granules. In these solid dosage forms, the active compound is mixed with at least one conventional inert excipient (or carrier), such as sodium citrate or dicalcium phosphate, or with the following ingredients: (a) fillers or compatibilizers, such as starch, lactose, sucrose, glucose, mannitol, and silicic acid; (b) binders, such as hydroxymethyl cellulose, alginates, gelatin, polyvinylpyrrolidone, sucrose, and gum arabic; (c) humectants, such as glycerin; (d) disintegrating agents, such as agar-agar, calcium carbonate, potato starch or tapioca starch, alginic acid, certain complex silicates, and sodium carbonate; (e) solution retarders, such as paraffin; (f) absorption accelerators, such as quaternary amine compounds; (g) wetting agents, such as cetyl alcohol and glyceryl monostearate; (h) adsorbents, such as kaolin; (i) lubricants, such as talc, calcium stearate, magnesium stearate, solid polyethylene glycol, sodium dodecyl sulfate, or mixtures thereof. In the case of capsules, tablets and pills, the dosage forms may also include buffering agents.

[0057] Solid dosage forms such as tablets, dragees, capsules, pills, and granules can be prepared using coating and shell materials, such as sausages and other materials known to those skilled in the art. These may contain opacifying agents, so that the release of the active compound or compounds in such compositions may be delayed in a certain part of the digestive tract. Examples of encapsulating materials that can be used include polymeric substances and wax-like substances. If necessary, the active compound may be formed into a microcapsule form with one or more of the above-mentioned excipients.

[0058] Liquid dosage forms for oral administration include pharmaceutically acceptable emulsions, solutions, suspensions, syrups, or tinctures. In addition to the active compound, the liquid dosage forms may contain inert diluents conventionally used in the art, such as water or other solvents, solubilizers, and emulsifiers, such as ethanol, isopropyl alcohol, ethyl carbonate, ethyl acetate, propylene glycol, 1,3-butanediol, dimethylformamide, oils, especially cottonseed oil, peanut oil, corn germ oil, olive oil, castor oil, sesame oil, or mixtures thereof.

[0059] In addition to these inert diluents, the compositions may also contain auxiliary substances such as wetting agents, emulsifying agents and suspending agents, sweeteners, flavoring agents and perfumes. In addition to the active compounds, suspensions may contain suspending agents such as ethoxylated isostearyl alcohol, polyoxyethylene sorbitol and sorbitan esters, microcrystalline cellulose, aluminum methoxide and agar, or mixtures thereof.

[0060] Compositions for parenteral injection may include physiologically acceptable sterile aqueous or non-aqueous solutions, dispersions, suspensions or emulsions, and sterile powders for reconstitution into sterile injectable solutions or dispersions. Suitable aqueous and non-aqueous carriers, diluents, solvents or excipients include water, ethanol, polyols and suitable mixtures thereof.

[0061] Dosage forms of the compounds of the present invention for topical administration include ointments, powders, patches, propellants, and inhalants. The active ingredient may be mixed under sterile conditions with a physiologically acceptable carrier and any preservatives, buffers, or propellants as may be required. The compounds of the present invention can be administered alone or in combination with other pharmaceutically acceptable compounds.

[0062] When using the pharmaceutical composition, a safe and effective amount of the compound of the present invention is administered to a mammal (e.g., human) in need of treatment, at a dosage considered to be pharmaceutically effective, and the daily dosage for a human weighing 60 kg is usually 1 to 2000 mg, preferably 5 to 500 mg. Of course, the specific dosage should take into account factors such as the route of administration and the patient's health condition, all of which are within the skill of a skilled physician.

[0063] The main advantages of the present invention include: The present invention provides a pentacyclic triterpenoid C-glycoside derivative compound represented by general formula I, or a pharmaceutically acceptable salt thereof, a racemate, an R-isomer, an S-isomer, or a mixture thereof: The present invention also provides a method for producing the above compound.

[0064] The present invention also provides use of the above-mentioned pentacyclic triterpenoid C-glycoside derivative compound or a pharmaceutically acceptable salt thereof, racemic form, R-form or S-form, or a mixture thereof in the manufacture of a drug for treating or preventing metabolic diseases such as diabetes mellitus and hyperlipidemia.

[0065] The present invention will be further described below with reference to specific examples. Note that these examples are only used to explain the present invention and are not used to limit the scope of the present invention. Experimental methods for which specific conditions are not described in the following examples are usually performed according to standard conditions or conditions suggested by manufacturers. Unless otherwise specified, percentages and parts are weight percentages and weight parts.

[0066] The experimental materials and reagents used in the following examples are commercially available unless otherwise specified. The present invention will be further illustrated and described in the following examples, which are used only to illustrate the present invention, but are not intended to limit the present invention.

[0067] Example 1 (3S,5S,8R,9R,10S,14R,17R,18S)-28-O-benzyloleanolic acid-3-(1'R)-(hydroxy)methyl-2'',3'',4'',6''-O-tetrabenzyl-β-D-glucopyranoside (A1) [ka]

[0068] The compound (3S,5S,8R,9R,10S,14R,17R,18S)-28-O-benzyl-3-aldehyde oleanolic acid (100.0 mg, 0.18 mmol) and 2,3,4,6-O-tetrabenzyl-1-(pyridin-1-yl)sulfonyl-β-D-thioglucopyranoside (207.7 mg, 0.36 mmol) were dissolved in 15 mL of double-distilled tetrahydrofuran and heated at 0°C with 0.1 mol / L diiodobenzoate under the protection of argon. A solution of samarium chloride in tetrahydrofuran (15 mL, 1.5 mmol) was added and stirred for 1 hour. After the reaction was complete as monitored by TLC, it was quenched by adding saturated ammonium chloride, extracted with dichloromethane, the organic layers were combined and washed with saturated sodium chloride solution, the organic layers were dried over anhydrous sodium sulfate and concentrated, and the crude product was subjected to column chromatography to give the title product A1 (152 mg, 78%). 1H NMR (600 MHz, CDCl3) δ 7.40 - 7.08 (m, 26H), 5.29 (t, J = 3.4 Hz, 1H), 5.05 (dt, J = 16.2, 11.9 Hz, 3H), 4.95 (d, J = 11.0 Hz, 1H), 4.83 (dd, J = 19.7, 11.0 Hz, 2H), 4.74 (d, J = 11.2 Hz, 1H), 4.65 - 4.47 (m, 3H), 4.01 (d, J = 5.8 Hz, 1H), 3.78 (t, J = 8.9 Hz, 1H), 3.68 (s, 1H), 3.66 - 3.62 (m, 1H), 3.58 (t, J = 9.1 Hz, 1H), 3.39 (dt, J = 9.7, 3.0 Hz, 1H), 3.31 (dd, J = 9.2, 6.7 Hz, 1H), 2.89 (dd, J = 13.6, 4.0 Hz, 1H), 1.98 (td, J = 13.5, 3.9 Hz, 1H), 1.87 - 1.76 (m, 2H), 1.26 (s, 3H), 1.12 (s, 3H), 0.94 (s, 3H), 0.91 (d, J = 1.5 Hz, 4H), 0.89 (s, 3H), 0.85 (s, 3H), 0.61 (s, 3H). LRMS (ESI): 1083.66 [M+H] + .

[0069] Example 2 (3S, 5S, 8R, 9R, 10S, 14R, 17R, 18S)-オレアノHelic acid-3-(1'R)-(ヒドロキシ)メチル-β-D-グルコピラノシド(A2)

change

[0070] The compound (3S,5S,8R,9R,10S,14R,17R,18S)-28-O-benzyl-3-aldehyde oleanolic acid (100.0 mg, 0.18 mmol) and 2,3,4,6-O-tetrabenzyl-1-(pyridin-1-yl)sulfonyl-β-D-thioglucopyranoside (207.7 mg, 0.36 mmol) were dissolved in 15 mL of redistilled tetrahydrofuran. Under argon protection, 0.1 mol / L samarium diiodide in tetrahydrofuran (15 mL, 1.5 mmol) was added at 0 °C. The mixture was stirred for 1 h and monitored by TLC. After the reaction was complete, the mixture was quenched with saturated ammonium chloride and extracted with dichloromethane. The combined organic layers were washed with saturated sodium chloride solution. The organic layers were dried over anhydrous sodium sulfate and concentrated. The crude product was subjected to column chromatography to obtain 152 mg of compound A1. Then, A1 was dissolved in ethyl acetate:methanol (15 mL:15 mL), and 30 mg of Pd / C was added in a hydrogen gas atmosphere. The mixture was reacted at 50°C for 12 hours, and then purified by column chromatography to obtain the title product A2 (70 mg, 79%). 1 H NMR (500 MHz, MeOD) δ 5.28 (s, 1H), 4.16 (s, 1H), 3.79 (d, J = 2.0 Hz, 2H), 3.46 (dd, J = 20.4, 9.3 Hz, 2H), 3.38 (s, 1H), 3.35 - 3.31 (m, 1H), 3.23 (d, J = 9.5 Hz, 1H), 3.11 (d, J = 9.5 Hz, 1H), 2.88 (dd, J = 13.5, 3.0 Hz, 1H), 2.03 (dd, J = 13.5, 10.3 Hz, 1H), 1.93 (d, J = 7.1Hz, 2H), 1.86 - 1.05 (m, 21H), 1.06 - 0.93 (m, 12H), 0.90 - 0.82 (m, 6H), 0.81 (d, J = 11.4 Hz, 1H). LRMS (ESI):631.43 [MH] - .

[0071] Example 3 (3R,5S,8R,9R,10S,14R,17R,18S)-28-O-benzyloleanolic acid-3-(1'R)-(hydroxy)methyl-2'',3'',4'',6''-O-tetrabenzyl-β-D-glucopyranoside (A3)

[0072] The remaining raw materials, reagents and production method were the same as in Example 1, except that (3S,5S,8R,9R,10S,14R,17R,18S)-28-O-benzyl-3-aldehyde oleanolic acid was changed to (3R,5S,8R,9R,10S,14R,17R,18S)-28-O-benzyl-3-aldehyde oleanolic acid, and A3 (yield 85%) was obtained. 1 H NMR (600 MHz, CDCl3) δ 7.40 - 7.08 (m, 26H), 5.29 (t, J = 3.4 Hz, 1H), 5.05 (dt, J = 16.2, 11.9 Hz, 3H), 4.95 (d, J = 11.0 Hz, 1H), 4.83 (dd, J = 19.7, 11.0 Hz, 2H), 4.74 (d, J = 11.2 Hz, 1H), 4.65 - 4.47 (m, 3H), 4.01 (d, J = 5.8 Hz, 1H), 3.78 (t, J = 8.9 Hz, 1H), 3.68 (s, 1H), 3.66 - 3.62 (m, 1H), 3.58 (t, J = 9.1 Hz, 1H), 3.39 (dt, J = 9.7, 3.0 Hz, 1H), 3.31 (dd, J = 9.2, 6.7 Hz, 1H), 2.89 (dd, J = 13.6, 4.0 Hz, 1H), 1.98 (td, J = 13.5, 3.9 Hz, 1H), 1.87 - 1.76 (m, 2H), 1.26 (s, 3H), 1.12 (s, 3H), 0.94 (s, 3H), 0.91 (d, J = 1.5 Hz, 4H), 0.89 (s, 3H), 0.85 (s, 3H), 0.61 (s, 3H). LRMS (ESI): 1083.66 [M+H] + .

[0073] Example 4 (3R,5S,8R,9R,10S,14R,17R,18S)-Oleanolic acid-3-(1'R)-(hydroxy)methyl-β-D-glucopyranoside (A4) (3S,5S,8R,9R,10S,14R,17R,18S)-28-O-benzyl-3-aldehyde oleanolic acid was changed to (3R,5S,8R,9R,10S,14R,17R,18S)-3-aldehyde oleanolic acid. The remaining raw materials, reagents, and production method were the same as in Example 2, and A4 (yield 74%) was obtained. 1 H NMR (500 MHz, MeOD) δ 5.28 (s, 1H), 4.16 (s, 1H), 3.79 (d, J = 2.0 Hz, 2H), 3.46 (dd, J = 20.4, 9.3 Hz, 2H), 3.38 (s, 1H), 3.35 - 3.31 (m, 1H), 3.23 (d, J = 9.5 Hz, 1H), 3.11 (d, J = 9.5 Hz, 1H), 2.88 (dd, J = 13.5, 3.0 Hz, 1H), 2.03 (dd, J = 13.5, 10.3 Hz, 1H), 1.93 (d, J = 7.1Hz, 2H), 1.86 - 1.05 (m, 21H), 1.06 - 0.93 (m, 12H), 0.90 - 0.82 (m, 6H), 0.81 (d, J = 11.4 Hz, 1H). LRMS (ESI):631.43 [MH] - .

[0074] Example 5 (3S,5S,8R,9R,10S,14R,17R,18S)-28-O-benzyloleanolic acid-3-methyl-2'',3'',4'',6''-O-tetrabenzyl-β-D-glucopyranoside (A5) [ka]

[0075] The compound (3S,5S,8R,9R,10S,14R,17R,18S)-28-O-benzyl-3-aldehyde oleanolic acid (66.7 mg, 0.12 mmol) and 2,3,4,6-O-tetrabenzyl-1-(pyridin-1-yl)sulfonyl-β-D-thioglucopyranoside (138.5 mg, 0.24 mmol) were dissolved in 15 mL of redistilled tetrahydrofuran. Under argon protection, 0.1 mol / L samarium diiodide in tetrahydrofuran (15 mL, 1.5 mmol) was added at 0 °C. The mixture was stirred for 1 h and monitored by TLC. After the reaction was complete, the mixture was quenched with saturated ammonium chloride and extracted with dichloromethane. The combined organic layers were washed with saturated sodium chloride solution. The organic layers were dried over anhydrous sodium sulfate and concentrated. The crude product was subjected to column chromatography to obtain 152 mg of compound A1. A1 was then dissolved in 10 mL of CS2, followed by the addition of NaH (15 mg, 0.37 mmol, 60% oil mixture) and stirring at room temperature for 2 hours. CHI (31 μL, 0.50 mmol) was then added and the reaction was allowed to proceed overnight. After completion of the reaction, as monitored by TLC, the reaction was quenched with saturated ammonium chloride and extracted with dichloromethane. The combined organic layers were washed with saturated sodium chloride, dried over anhydrous sodium sulfate, and concentrated. The crude product was subjected to column chromatography to obtain intermediate A. Intermediate A and AIBN (23 mg, 0.14 mmol) were dissolved in 20 mL of ultra-dry toluene, and tri-n-butyltin hydride (0.12 mL, 0.45 mmol) was added with stirring. The mixture was stirred at reflux for 4 hours. After completion of the reaction, as monitored by TLC, the mixture was concentrated and subjected to column chromatography to obtain the title product A5 (64 mg, 65%).

[0076] 1H NMR (600 MHz, CDCl3) δ 7.40 - 7.08 (m, 26H), 5.29 (t, J = 3.4 Hz, 1H), 5.05 (dt, J = 16.2, 11.9 Hz, 3H), 4.95 (d, J = 11.0 Hz, 1H), 4.83 (dd, J = 19.7, 11.0 Hz, 2H), 4.74 (d, J = 11.2 Hz, 1H), 4.65 - 4.47 (m, 3H), 4.01 (d, J = 5.8 Hz, 1H), 3.78 (t, J = 8.9 Hz, 1H), 3.68 (s, 1H), 3.66 - 3.62 (m, 1H), 3.58 (t, J = 9.1 Hz, 1H), 3.39 (dt, J = 9.7, 3.0 Hz, 1H), 3.31 (dd, J = 9.2, 6.7 Hz, 1H), 2.89 (dd, J = 13.6, 4.0 Hz, 1H), 1.98 (td, J = 13.5, 3.9 Hz, 1H), 1.87 - 1.76 (m, 2H), 1.26 (s, 3H), 1.12 (s, 3H), 0.94 (s, 3H), 0.91 (d, J = 1.5 Hz, 4H), 0.89 (s, 3H), 0.85 (s, 3H), 0.61 (s, 3H). LRMS (ESI): 1067.67 [M+H] + .

[0077] Example 6 (3S, 5S, 8R, 9R, 10S, 14R, 17R, 18S)-オレアノール acid-メチル-β-D-グルコピラノシド (A6)

change

[0078] 1H NMR (500 MHz, MeOD) δ 5.28 (s, 1H), 4.16 (s, 1H), 3.79 (d, J = 2.0 Hz, 2H), 3.46 (dd, J = 20.4, 9.3 Hz, 2H), 3.38 (s, 1H), 3.35 - 3.31 (m, 1H), 3.23 (d, J = 9.5 Hz, 1H), 3.11 (d, J = 9.5 Hz, 1H), 2.88 (dd, J = 13.5, 3.0 Hz, 1H), 2.03 (dd, J = 13.5, 10.3 Hz, 1H), 1.93 (d, J = 7.1Hz, 2H), 1.86 - 1.05 (m, 21H), 1.06 - 0.93 (m, 12H), 0.90 - 0.82 (m, 6H), 0.81 (d, J = 11.4 Hz, 1H). LRMS (ESI):615.43 [MH] - .

[0079] Example 7 (3R,5S,8R,9R,10S,14R,17R,18S)-28-O-benzyloleanolic acid-3-methyl-2'',3'',4'',6''-O-tetrabenzyl-β-D-glucopyranoside (A7) A7 (yield 67%) was obtained using the same raw materials, reagents and production method as in Example 5, except that (3S,5S,8R,9R,10S,14R,17R,18S)-28-O-benzyl-3-aldehyde oleanolic acid was changed to (3R,5S,8R,9R,10S,14R,17R,18S)-28-O-benzyl-3-aldehyde oleanolic acid. 1H NMR (600 MHz, CDCl3) δ 7.40 - 7.08 (m, 26H), 5.29 (t, J = 3.4 Hz, 1H), 5.05 (dt, J = 16.2, 11.9 Hz, 3H), 4.95 (d, J = 11.0 Hz, 1H), 4.83 (dd, J = 19.7, 11.0 Hz, 2H), 4.74 (d, J = 11.2 Hz, 1H), 4.65 - 4.47 (m, 3H), 4.01 (d, J = 5.8 Hz, 1H), 3.78 (t, J = 8.9 Hz, 1H), 3.68 (s, 1H), 3.66 - 3.62 (m, 1H), 3.58 (t, J = 9.1 Hz, 1H), 3.39 (dt, J = 9.7, 3.0 Hz, 1H), 3.31 (dd, J = 9.2, 6.7 Hz, 1H), 2.89 (dd, J = 13.6, 4.0 Hz, 1H), 1.98 (td, J = 13.5, 3.9 Hz, 1H), 1.87 - 1.76 (m, 2H), 1.26 (s, 3H), 1.12 (s, 3H), 0.94 (s, 3H), 0.91 (d, J = 1.5 Hz, 4H), 0.89 (s, 3H), 0.85 (s, 3H), 0.61 (s, 3H). LRMS (ESI): 1067.67 [M+H] + .

[0080] Example 8 (3R,5S,8R,9R,10S,14R,17R,18S)-oleanolic acid-3-methyl-β-D-glucopyranoside (A8) The remaining raw materials, reagents and production method were the same as in Example 6, except that (3S,5S,8R,9R,10S,14R,17R,18S)-28-O-benzyl-3-aldehyde oleanolic acid was changed to (3R,5S,8R,9R,10S,14R,17R,18S)-28-O-benzyl-3-aldehyde oleanolic acid, and A8 (yield 71%) was obtained. 1H NMR (500 MHz, MeOD) δ 5.28 (s, 1H), 4.16 (s, 1H), 3.79 (d, J = 2.0 Hz, 2H), 3.46 (dd, J = 20.4, 9.3 Hz, 2H), 3.38 (s, 1H), 3.35 - 3.31 (m, 1H), 3.23 (d, J = 9.5 Hz, 1H), 3.11 (d, J = 9.5 Hz, 1H), 2.88 (dd, J = 13.5, 3.0 Hz, 1H), 2.03 (dd, J = 13.5, 10.3 Hz, 1H), 1.93 (d, J = 7.1 Hz, 2H), 1.86 - 1.05 (m, 21H), 1.06 - 0.93 (m, 12H), 0.90 - 0.82 (m, 6H), 0.81 (d, J = 11.4 Hz, 1H). LRMS (ESI): 615.43 [MH] - .

[0081] Example 9 (3S, 5S, 8R, 9R, 10S, 14R, 17R, 18S)-28-O-ベンジルオレアノール acid -3-カルボニル-2'',3'',4'',6''-O-テトラベンジル-β-D-グルコピラノシド(A9)

change

[0082] The compound (3S,5S,8R,9R,10S,14R,17R,18S)-28-O-benzyl-3-aldehyde oleanolic acid (66.7 mg, 0.12 mmol) and 2,3,4,6-O-tetrabenzyl-1-(pyridin-1-yl)sulfonyl-β-D-thioglucopyranoside (138.5 mg, 0.24 mmol) were dissolved in 15 mL of redistilled tetrahydrofuran. Under argon protection, 0.1 mol / L samarium diiodide in tetrahydrofuran (15 mL, 1.5 mmol) was added at 0 °C. The mixture was stirred for 1 h and monitored by TLC. After the reaction was complete, the mixture was quenched with saturated ammonium chloride and extracted with dichloromethane. The combined organic layers were washed with saturated sodium chloride solution. The organic layers were dried over anhydrous sodium sulfate and concentrated. The crude product was subjected to column chromatography to obtain 152 mg of compound A1. A1 was then dissolved in 10 mL of dichloromethane, followed by the addition of Dess-Martin reagent (76 mg, 0.18 mmol) and stirring at room temperature for 2 h. After completion of the reaction as monitored by TLC, the reaction was quenched with saturated sodium thiosulfate and extracted with dichloromethane. The combined organic layers were washed with saturated sodium chloride, dried over anhydrous sodium sulfate, and concentrated. The crude product was subjected to column chromatography to give the title product A9 (90 mg, 90%). 1H NMR (600 MHz, CDCl3) δ 7.40 - 7.08 (m, 26H), 5.29 (t, J = 3.4 Hz, 1H), 5.05 (dt, J = 16.2, 11.9 Hz, 3H), 4.95 (d, J = 11.0 Hz, 1H), 4.83 (dd, J = 19.7, 11.0 Hz, 2H), 4.74 (d, J = 11.2 Hz, 1H), 4.65 - 4.47 (m, 3H), 4.01 (d, J = 5.8 Hz, 1H), 3.78 (t, J = 8.9 Hz, 1H), 3.68 (s, 1H), 3.66 - 3.62 (m, 1H), 3.58 (t, J = 9.1 Hz, 1H), 3.39 (dt, J = 9.7, 3.0 Hz, 1H), 3.31 (dd, J = 9.2, 6.7 Hz, 1H), 2.89 (dd, J = 13.6, 4.0 Hz, 1H), 1.98 (td, J = 13.5, 3.9 Hz, 1H), 1.87 - 1.76 (m, 2H), 1.26 (s, 3H), 1.12 (s, 3H), 0.94 (s, 3H), 0.91 (d, J = 1.5 Hz, 4H), 0.89 (s, 3H), 0.85 (s, 3H), 0.61 (s, 3H). LRMS (ESI): 1081.65 [M+H] + .

[0083] Example 10 (3S, 5S, 8R, 9R, 10S, 14R, 17R, 18S)-オレアノール acid-3-カルボニル-β-D-グルコピラノシド (A10)

change

[0084] The compound (3S,5S,8R,9R,10S,14R,17R,18S)-28-O-benzyl-3-aldehyde oleanolic acid (66.7 mg, 0.12 mmol) and 2,3,4,6-O-tetrabenzyl-1-(pyridin-1-yl)sulfonyl-β-D-thioglucopyranoside (138.5 mg, 0.24 mmol) were dissolved in 15 mL of redistilled tetrahydrofuran. Under the protection of argon, a 0.1 mol / L solution of samarium diiodide in tetrahydrofuran (15 mL, 1.5 mmol) was added at 0 °C. The mixture was stirred for 1 hour and monitored by TLC. After the reaction was complete, the mixture was quenched with saturated ammonium chloride and extracted with dichloromethane. The combined organic layers were washed with saturated sodium chloride solution. The organic layers were dried over anhydrous sodium sulfate and concentrated. The crude product was subjected to column chromatography to obtain A1. A1 was then dissolved in 10 mL of dichloromethane, followed by the addition of Dess-Martin reagent (76 mg, 0.18 mmol) and stirring at room temperature for 2 h. After completion of the reaction as monitored by TLC, the reaction was quenched with saturated sodium thiosulfate and extracted with dichloromethane. The combined organic layers were washed with saturated sodium chloride, dried over anhydrous sodium sulfate, and concentrated. The crude product was subjected to column chromatography to give 90 mg of A9. A9 was then dissolved in 15 mL of ethyl acetate:methanol (15 mL:15 mL), and heated under hydrogen gas at 50 °C with 13 mg of Pd / C for 12 h. The resulting mixture was then purified by column chromatography to give the title product A10 (38 mg, 73%).

[0085] 1H NMR (500 MHz, MeOD) δ 5.28 (s, 1H), 4.16 (s, 1H), 3.79 (d, J = 2.0 Hz, 2H), 3.46 (dd, J = 20.4, 9.3 Hz, 2H), 3.38 (s, 1H), 3.35 - 3.31 (m, 1H), 3.23 (d, J = 9.5 Hz, 1H), 3.11 (d, J = 9.5 Hz, 1H), 2.88 (dd, J = 13.5, 3.0 Hz, 1H), 2.03 (dd, J = 13.5, 10.3 Hz, 1H), 1.93 (d, J = 7.1Hz, 2H), 1.86 - 1.05 (m, 21H), 1.06 - 0.93 (m, 12H), 0.90 - 0.82 (m, 6H), 0.81 (d, J = 11.4 Hz, 1H). LRMS (ESI):629.41 [MH] - .

[0086] Example 11 (3R,5S,8R,9R,10S,14R,17R,18S)-28-O-benzyloleanolic acid-3-carbonyl-2'',3'',4'',6''-O-tetrabenzyl-β-D-glucopyranoside (A11) A11 (yield 89%) was obtained using the same raw materials, reagents and production method as in Example 9, except that (3S,5S,8R,9R,10S,14R,17R,18S)-28-O-benzyl-3-aldehyde oleanolic acid was used instead of (3R,5S,8R,9R,10S,14R,17R,18S)-28-O-benzyl-3-aldehyde oleanolic acid. 1H NMR (600 MHz, CDCl3) δ 5.28 (s, 1H), 4.16 (s, 1H), 3.79 (d, J = 2.0 Hz, 2H), 3.46 (dd, J = 20.4, 9.3 Hz, 2H), 3.38 (s, 1H), 3.35 - 3.31 (m, 1H), 3.23 (d, J = 9.5 Hz, 1H), 3.11 (d, J = 9.5 Hz, 1H), 2.88 (dd, J = 13.5, 3.0 Hz, 1H), 2.03 (dd, J = 13.5, 10.3 Hz, 1H), 1.93 (d, J = 7.1 Hz, 2H), 1.86 - 1.05 (m, 21H), 1.06 - 0.93 (m, 12H), 0.90 - 0.82 (m, 6H), 0.81 (d, J = 11.4 Hz, 1H). LRMS (ESI): 1081.65 [M+H] + .

[0087] Example 12 (3R,5S,8R,9R,10S,14R,17R,18S)-oleanolic acid-3-carbonyl-β-D-glucopyranoside (A12) A12 (yield 91%) was obtained using the same raw materials, reagents and production method as in Example 10, except that (3S,5S,8R,9R,10S,14R,17R,18S)-28-O-benzyl-3-aldehyde oleanolic acid was changed to (3R,5S,8R,9R,10S,14R,17R,18S)-28-O-benzyl-3-aldehyde oleanolic acid. 1H NMR (500 MHz, MeOD) δ 5.28 (s, 1H), 4.16 (s, 1H), 3.79 (d, J = 2.0 Hz, 2H), 3.46 (dd, J = 20.4, 9.3 Hz, 2H), 3.38 (s, 1H), 3.35 - 3.31 (m, 1H), 3.23 (d, J = 9.5 Hz, 1H), 3.11 (d, J = 9.5 Hz, 1H), 2.88 (dd, J = 13.5, 3.0 Hz, 1H), 2.03 (dd, J = 13.5, 10.3 Hz, 1H), 1.93 (d, J = 7.1Hz, 2H), 1.86 - 1.05 (m, 21H), 1.06 - 0.93 (m, 12H), 0.90 - 0.82 (m, 6H), 0.81 (d, J = 11.4 Hz, 1H). LRMS (ESI):629.41 [MH] - .

[0088] Example 13 (3S,5S,8R,9R,10S,14R,17R,18S)-oleanolic acid-3-(1'R)-(hydroxy)methyl-β-D-galactopyranoside (A13) The remaining raw materials, reagents, and production method were the same as in Example 2, except that 2,3,4,6-O-tetrabenzyl-1-(pyridin-1-yl)sulfonyl-β-D-thiogalactopyranoside was used instead of 2,3,4,6-O-tetrabenzyl-1-(pyridin-1-yl)sulfonyl-β-D-thiogalactopyranoside. A13 (yield 77%) was obtained using the same method as in Example 2. 1H NMR (500 MHz, MeOD) δ 5.28 (s, 1H), 4.16 (s, 1H), 3.79 (d, J = 2.0 Hz, 2H), 3.46 (dd, J = 20.4, 9.3 Hz, 2H), 3.38 (s, 1H), 3.35 - 3.31 (m, 1H), 3.23 (d, J = 9.5 Hz, 1H), 3.11 (d, J = 9.5 Hz, 1H), 2.88 (dd, J = 13.5, 3.0 Hz, 1H), 2.03 (dd, J = 13.5, 10.3 Hz, 1H), 1.93 (d, J = 7.1Hz, 2H), 1.86 - 1.05 (m, 21H), 1.06 - 0.93 (m, 12H), 0.90 - 0.82 (m, 6H), 0.81 (d, J = 11.4 Hz, 1H). LRMS (ESI):631.43 [MH] - .

[0089] Example 14 (3R,5S,8R,9R,10S,14R,17R,18S)-Oleanolic acid-3-(1'R)-(hydroxy)methyl-β-D-galactopyranoside (A14) The remaining raw materials, reagents, and production method were the same as in Example 2, but with the exception of 2,3,4,6-O-tetrabenzyl-1-(pyridin-1-yl)sulfonyl-β-D-thioglucopyranoside being replaced with 2,3,4,6-O-tetrabenzyl-1-(pyridin-1-yl)sulfonyl-β-D-thiogalactopyranoside, and (3S,5S,8R,9R,10S,14R,17R,18S)-28-O-benzyl-3-aldehyde oleanolic acid being replaced with (3R,5S,8R,9R,10S,14R,17R,18S)-28-O-benzyl-3-aldehyde oleanolic acid. A14 (yield 74%) was obtained using the same method as in Example 2. 1H NMR (500 MHz, MeOD) δ 5.28 (s, 1H), 4.16 (s, 1H), 3.79 (d, J = 2.0 Hz, 2H), 3.46 (dd, J = 20.4, 9.3 Hz, 2H), 3.38 (s, 1H), 3.35 - 3.31 (m, 1H), 3.23 (d, J = 9.5 Hz, 1H), 3.11 (d, J = 9.5 Hz, 1H), 2.88 (dd, J = 13.5, 3.0 Hz, 1H), 2.03 (dd, J = 13.5, 10.3 Hz, 1H), 1.93 (d, J = 7.1Hz, 2H), 1.86 - 1.05 (m, 21H), 1.06 - 0.93 (m, 12H), 0.90 - 0.82 (m, 6H), 0.81 (d, J = 11.4 Hz, 1H). LRMS (ESI):631.43 [MH] - .

[0090] Example 15 (3S,5S,8R,9R,10S,14R,17R,18S)-oleanolic acid-3-methyl-β-D-galactopyranoside (A15) A15 (yield 63%) was obtained using the same raw materials, reagents, and production method as in Example 6, except that 2,3,4,6-O-tetrabenzyl-1-(pyridin-1-yl)sulfonyl-β-D-thioglucopyranoside was used instead of 2,3,4,6-O-tetrabenzyl-1-(pyridin-1-yl)sulfonyl-β-D-thiogalactopyranoside. 1H NMR (500 MHz, MeOD) δ 5.28 (s, 1H), 4.16 (s, 1H), 3.79 (d, J = 2.0 Hz, 2H), 3.46 (dd, J = 20.4, 9.3 Hz, 2H), 3.38 (s, 1H), 3.35 - 3.31 (m, 1H), 3.23 (d, J = 9.5 Hz, 1H), 3.11 (d, J = 9.5 Hz, 1H), 2.88 (dd, J = 13.5, 3.0 Hz, 1H), 2.03 (dd, J = 13.5, 10.3 Hz, 1H), 1.93 (d, J = 7.1Hz, 2H), 1.86 - 1.05 (m, 21H), 1.06 - 0.93 (m, 12H), 0.90 - 0.82 (m, 6H), 0.81 (d, J = 11.4 Hz, 1H). LRMS (ESI):615.43 [MH] - .

[0091] Example 16 (3R,5S,8R,9R,10S,14R,17R,18S)-oleanolic acid-3-methyl-β-D-galactopyranoside (A16) The remaining raw materials, reagents, and production method were the same as in Example 6, except that 2,3,4,6-O-tetrabenzyl-1-(pyridin-1-yl)sulfonyl-β-D-thioglucopyranoside was changed to 2,3,4,6-O-tetrabenzyl-1-(pyridin-1-yl)sulfonyl-β-D-thiogalactopyranoside and (3S,5S,8R,9R,10S,14R,17R,18S)-28-O-benzyl-3-aldehyde oleanolic acid was changed to (3R,5S,8R,9R,10S,14R,17R,18S)-28-O-benzyl-3-aldehyde oleanolic acid, and A16 (yield 74%) was obtained. 1H NMR (500 MHz, MeOD) δ 5.28 (s, 1H), 4.16 (s, 1H), 3.79 (d, J = 2.0 Hz, 2H), 3.46 (dd, J = 20.4, 9.3 Hz, 2H), 3.38 (s, 1H), 3.35 - 3.31 (m, 1H), 3.23 (d, J = 9.5 Hz, 1H), 3.11 (d, J = 9.5 Hz, 1H), 2.88 (dd, J = 13.5, 3.0 Hz, 1H), 2.03 (dd, J = 13.5, 10.3 Hz, 1H), 1.93 (d, J = 7.1Hz, 2H), 1.86 - 1.05 (m, 21H), 1.06 - 0.93 (m, 12H), 0.90 - 0.82 (m, 6H), 0.81 (d, J = 11.4 Hz, 1H). LRMS (ESI):615.43 [MH] - .

[0092] Example 17 (3S,5S,8R,9R,10S,14R,17R,18S)-Oleanolic acid-3-carbonyl-β-D-galactopyranoside (A17) A17 (yield 81%) was obtained using the same raw materials, reagents, and production method as in Example 10, except that 2,3,4,6-O-tetrabenzyl-1-(pyridin-1-yl)sulfonyl-β-D-thioglucopyranoside was replaced with 2,3,4,6-O-tetrabenzyl-1-(pyridin-1-yl)sulfonyl-β-D-thiogalactopyranoside. 1H NMR (500 MHz, MeOD) δ 5.28 (s, 1H), 4.16 (s, 1H), 3.79 (d, J = 2.0 Hz, 2H), 3.46 (dd, J = 20.4, 9.3 Hz, 2H), 3.38 (s, 1H), 3.35 - 3.31 (m, 1H), 3.23 (d, J = 9.5 Hz, 1H), 3.11 (d, J = 9.5 Hz, 1H), 2.88 (dd, J = 13.5, 3.0 Hz, 1H), 2.03 (dd, J = 13.5, 10.3 Hz, 1H), 1.93 (d, J = 7.1Hz, 2H), 1.86 - 1.05 (m, 21H), 1.06 - 0.93 (m, 12H), 0.90 - 0.82 (m, 6H), 0.81 (d, J = 11.4 Hz, 1H). LRMS (ESI):629.41 [MH] - .

[0093] Example 18 (3R,5S,8R,9R,10S,14R,17R,18S)-Oleanolic acid-3-carbonyl-β-D-galactopyranoside (A18) The remaining raw materials, reagents, and production method were the same as in Example 10, except that 2,3,4,6-O-tetrabenzyl-1-(pyridin-1-yl)sulfonyl-β-D-thioglucopyranoside was changed to 2,3,4,6-O-tetrabenzyl-1-(pyridin-1-yl)sulfonyl-β-D-thiogalactopyranoside and (3S,5S,8R,9R,10S,14R,17R,18S)-28-O-benzyl-3-aldehyde oleanolic acid was changed to (3R,5S,8R,9R,10S,14R,17R,18S)-28-O-benzyl-3-aldehyde oleanolic acid. A18 (yield 86%) was obtained using the same raw materials, reagents, and production method as in Example 10. 1H NMR (500 MHz, MeOD) δ 5.28 (s, 1H), 4.16 (s, 1H), 3.79 (d, J = 2.0 Hz, 2H), 3.46 (dd, J = 20.4, 9.3 Hz, 2H), 3.38 (s, 1H), 3.35 - 3.31 (m, 1H), 3.23 (d, J = 9.5 Hz, 1H), 3.11 (d, J = 9.5 Hz, 1H), 2.88 (dd, J = 13.5, 3.0 Hz, 1H), 2.03 (dd, J = 13.5, 10.3 Hz, 1H), 1.93 (d, J = 7.1Hz, 2H), 1.86 - 1.05 (m, 21H), 1.06 - 0.93 (m, 12H), 0.90 - 0.82 (m, 6H), 0.81 (d, J = 11.4 Hz, 1H). LRMS (ESI):629.41 [MH] - .

[0094] Example 19 (3S,5S,8R,9R,10S,14R,17R,18S)-oleanolic acid-3-(1'S)-(hydroxy)methyl-α-D-mannopyranoside (A19) The remaining raw materials, reagents, and production method were the same as in Example 2, except that 2,3,4,6-O-tetrabenzyl-1-(pyridin-1-yl)sulfonyl-β-D-thioglucopyranoside was replaced with 2,3,4,6-O-tetrabenzyl-1-(pyridin-1-yl)sulfonyl-α-D-thiomannopyranoside. A19 (yield 73%) was obtained using the same method as in Example 2. 1H NMR (500 MHz, MeOD) δ 5.28 (s, 1H), 4.16 (s, 1H), 3.79 (d, J = 2.0 Hz, 2H), 3.46 (dd, J = 20.4, 9.3 Hz, 2H), 3.38 (s, 1H), 3.35 - 3.31 (m, 1H), 3.23 (d, J = 9.5 Hz, 1H), 3.11 (d, J = 9.5 Hz, 1H), 2.88 (dd, J = 13.5, 3.0 Hz, 1H), 2.03 (dd, J = 13.5, 10.3 Hz, 1H), 1.93 (d, J = 7.1Hz, 2H), 1.86 - 1.05 (m, 21H), 1.06 - 0.93 (m, 12H), 0.90 - 0.82 (m, 6H), 0.81 (d, J = 11.4 Hz, 1H). LRMS (ESI):631.43 [MH] - .

[0095] Example 20 (3R,5S,8R,9R,10S,14R,17R,18S)-oleanolic acid-3-(1'S)-(hydroxy)methyl-α-D-mannopyranoside (A20) The remaining raw materials, reagents, and production method were the same as in Example 2, but with the exception of 2,3,4,6-O-tetrabenzyl-1-(pyridin-1-yl)sulfonyl-β-D-thioglucopyranoside being replaced with 2,3,4,6-O-tetrabenzyl-1-(pyridin-1-yl)sulfonyl-α-D-thiomannopyranoside, and (3S,5S,8R,9R,10S,14R,17R,18S)-28-O-benzyl-3-aldehyde oleanolic acid being replaced with (3R,5S,8R,9R,10S,14R,17R,18S)-28-O-benzyl-3-aldehyde oleanolic acid. A20 (yield 62%) was obtained using the same method as in Example 2. 1H NMR (500 MHz, MeOD) δ 5.28 (s, 1H), 4.16 (s, 1H), 3.79 (d, J = 2.0 Hz, 2H), 3.46 (dd, J = 20.4, 9.3 Hz, 2H), 3.38 (s, 1H), 3.35 - 3.31 (m, 1H), 3.23 (d, J = 9.5 Hz, 1H), 3.11 (d, J = 9.5 Hz, 1H), 2.88 (dd, J = 13.5, 3.0 Hz, 1H), 2.03 (dd, J = 13.5, 10.3 Hz, 1H), 1.93 (d, J = 7.1Hz, 2H), 1.86 - 1.05 (m, 21H), 1.06 - 0.93 (m, 12H), 0.90 - 0.82 (m, 6H), 0.81 (d, J = 11.4 Hz, 1H). LRMS (ESI):631.43 [MH] - .

[0096] Example 21 (3S,5S,8R,9R,10S,14R,17R,18S)-oleanolic acid-3-methyl-α-D-mannopyranoside (A21) Except for changing 2,3,4,6-O-tetrabenzyl-1-(pyridin-1-yl)sulfonyl-β-D-thioglucopyranoside to 2,3,4,6-O-tetrabenzyl-1-(pyridin-1-yl)sulfonyl-α-D-thiomannopyranoside, the remaining raw materials, reagents and production method were the same as in Example 6, and A21 (yield 65%) was obtained. 1H NMR (500 MHz, MeOD) δ 5.28 (s, 1H), 4.16 (s, 1H), 3.79 (d, J = 2.0 Hz, 2H), 3.46 (dd, J = 20.4, 9.3 Hz, 2H), 3.38 (s, 1H), 3.35 - 3.31 (m, 1H), 3.23 (d, J = 9.5 Hz, 1H), 3.11 (d, J = 9.5 Hz, 1H), 2.88 (dd, J = 13.5, 3.0 Hz, 1H), 2.03 (dd, J = 13.5, 10.3 Hz, 1H), 1.93 (d, J = 7.1Hz, 2H), 1.86 - 1.05 (m, 21H), 1.06 - 0.93 (m, 12H), 0.90 - 0.82 (m, 6H), 0.81 (d, J = 11.4 Hz, 1H). LRMS (ESI):615.43 [MH] - .

[0097] Example 22 (3R,5S,8R,9R,10S,14R,17R,18S)-oleanolic acid-3-methyl-α-D-mannopyranoside (A22) The remaining raw materials, reagents, and preparation method were the same as in Example 6, but with the exception of 2,3,4,6-O-tetrabenzyl-1-(pyridin-1-yl)sulfonyl-β-D-thioglucopyranoside being replaced with 2,3,4,6-O-tetrabenzyl-1-(pyridin-1-yl)sulfonyl-α-D-thiomannopyranoside, and (3S,5S,8R,9R,10S,14R,17R,18S)-28-O-benzyl-3-aldehyde oleanolic acid being replaced with (3R,5S,8R,9R,10S,14R,17R,18S)-28-O-benzyl-3-aldehyde oleanolic acid. A22 (yield 64%) was obtained using the same method as in Example 6. 1H NMR (500 MHz, MeOD) δ 5.28 (s, 1H), 4.16 (s, 1H), 3.79 (d, J = 2.0 Hz, 2H), 3.46 (dd, J = 20.4, 9.3 Hz, 2H), 3.38 (s, 1H), 3.35 - 3.31 (m, 1H), 3.23 (d, J = 9.5 Hz, 1H), 3.11 (d, J = 9.5 Hz, 1H), 2.88 (dd, J = 13.5, 3.0 Hz, 1H), 2.03 (dd, J = 13.5, 10.3 Hz, 1H), 1.93 (d, J = 7.1Hz, 2H), 1.86 - 1.05 (m, 21H), 1.06 - 0.93 (m, 12H), 0.90 - 0.82 (m, 6H), 0.81 (d, J = 11.4 Hz, 1H). LRMS (ESI):615.43 [MH] - .

[0098] Example 23 (3S,5S,8R,9R,10S,14R,17R,18S)-oleanolic acid-3-carbonyl-α-D-mannopyranoside (A23) Except for changing 2,3,4,6-O-tetrabenzyl-1-(pyridin-1-yl)sulfonyl-β-D-thioglucopyranoside to 2,3,4,6-O-tetrabenzyl-1-(pyridin-1-yl)sulfonyl-α-D-thiomannopyranoside, the remaining raw materials, reagents, and production method were the same as in Example 10, and A23 (yield 91%) was obtained. 1H NMR (500 MHz, MeOD) δ 5.28 (s, 1H), 4.16 (s, 1H), 3.79 (d, J = 2.0 Hz, 2H), 3.46 (dd, J = 20.4, 9.3 Hz, 2H), 3.38 (s, 1H), 3.35 - 3.31 (m, 1H), 3.23 (d, J = 9.5 Hz, 1H), 3.11 (d, J = 9.5 Hz, 1H), 2.88 (dd, J = 13.5, 3.0 Hz, 1H), 2.03 (dd, J = 13.5, 10.3 Hz, 1H), 1.93 (d, J = 7.1Hz, 2H), 1.86 - 1.05 (m, 21H), 1.06 - 0.93 (m, 12H), 0.90 - 0.82 (m, 6H), 0.81 (d, J = 11.4 Hz, 1H). LRMS (ESI):629.41 [MH] - .

[0099] Example 24 (3R,5S,8R,9R,10S,14R,17R,18S)-oleanolic acid-3-carbonyl-α-D-mannopyranoside (A24) The remaining raw materials, reagents, and preparation method were the same as in Example 10, but with the exception of 2,3,4,6-O-tetrabenzyl-1-(pyridin-1-yl)sulfonyl-β-D-thioglucopyranoside being replaced with 2,3,4,6-O-tetrabenzyl-1-(pyridin-1-yl)sulfonyl-α-D-thiomannopyranoside, and (3S,5S,8R,9R,10S,14R,17R,18S)-28-O-benzyl-3-aldehyde oleanolic acid being replaced with (3R,5S,8R,9R,10S,14R,17R,18S)-28-O-benzyl-3-aldehyde oleanolic acid. A24 (yield 86%) was obtained using the same method as in Example 10. 1H NMR (500 MHz, MeOD) δ 5.28 (s, 1H), 4.16 (s, 1H), 3.79 (d, J = 2.0 Hz, 2H), 3.46 (dd, J = 20.4, 9.3 Hz, 2H), 3.38 (s, 1H), 3.35 - 3.31 (m, 1H), 3.23 (d, J = 9.5 Hz, 1H), 3.11 (d, J = 9.5 Hz, 1H), 2.88 (dd, J = 13.5, 3.0 Hz, 1H), 2.03 (dd, J = 13.5, 10.3 Hz, 1H), 1.93 (d, J = 7.1Hz, 2H), 1.86 - 1.05 (m, 21H), 1.06 - 0.93 (m, 12H), 0.90 - 0.82 (m, 6H), 0.81 (d, J = 11.4 Hz, 1H). LRMS (ESI):629.41 [MH] - .

[0100] Example 25 (3S,5S,8R,9R,10S,14R,17R,18S)-Oleanolic acid-3-(1'R)-(hydroxy)methyl-β-D-glucuronopyranoside (A25) The remaining raw materials, reagents, and production method were the same as in Example 2, except that 2,3,4,6-O-tetrabenzyl-1-(pyridin-1-yl)sulfonyl-β-D-thioglucuronopyranoside was used instead of 2,3,4,6-O-tetrabenzyl-1-(pyridin-1-yl)sulfonyl-β-D-thioglucuronopyranoside. A25 (yield 77%) was obtained using the same method as in Example 2. 1H NMR (500 MHz, MeOD) δ 5.28 (s, 1H), 4.16 (s, 1H), 3.79 (d, J = 2.0 Hz, 2H), 3.46 (dd, J = 20.4, 9.3 Hz, 2H), 3.38 (s, 1H), 3.35 - 3.31 (m, 1H), 3.23 (d, J = 9.5 Hz, 1H), 3.11 (d, J = 9.5 Hz, 1H), 2.88 (dd, J = 13.5, 3.0 Hz, 1H), 2.03 (dd, J = 13.5, 10.3 Hz, 1H), 1.93 (d, J = 7.1Hz, 2H), 1.86 - 1.05 (m, 21H), 1.06 - 0.93 (m, 12H), 0.90 - 0.82 (m, 6H), 0.81 (d, J = 11.4 Hz, 1H). LRMS (ESI):645.41 [MH] - .

[0101] Example 26 (3R,5S,8R,9R,10S,14R,17R,18S)-Oleanolic acid-3-(1'R)-(hydroxy)methyl-β-D-glucuronopyranoside (A26) The remaining raw materials, reagents, and production method were the same as in Example 2, but with the exception of 2,3,4,6-O-tetrabenzyl-1-(pyridin-1-yl)sulfonyl-β-D-thioglucopyranoside being replaced with 2,3,4,6-O-tetrabenzyl-1-(pyridin-1-yl)sulfonyl-β-D-thioglucuronopyranoside, and (3S,5S,8R,9R,10S,14R,17R,18S)-28-O-benzyl-3-aldehyde oleanolic acid being replaced with (3R,5S,8R,9R,10S,14R,17R,18S)-28-O-benzyl-3-aldehyde oleanolic acid. A26 (72% yield) was obtained using the same method as in Example 2. 1H NMR (500 MHz, MeOD) δ 5.28 (s, 1H), 4.16 (s, 1H), 3.79 (d, J = 2.0 Hz, 2H), 3.46 (dd, J = 20.4, 9.3 Hz, 2H), 3.38 (s, 1H), 3.35 - 3.31 (m, 1H), 3.23 (d, J = 9.5 Hz, 1H), 3.11 (d, J = 9.5 Hz, 1H), 2.88 (dd, J = 13.5, 3.0 Hz, 1H), 2.03 (dd, J = 13.5, 10.3 Hz, 1H), 1.93 (d, J = 7.1Hz, 2H), 1.86 - 1.05 (m, 21H), 1.06 - 0.93 (m, 12H), 0.90 - 0.82 (m, 6H), 0.81 (d, J = 11.4 Hz, 1H). LRMS (ESI):645.41 [MH] - .

[0102] Example 27 (3S,5S,8R,9R,10S,14R,17R,18S)-Oleanolic acid 3-methyl-β-D-glucuronopyranoside (A27) A27 (yield 65%) was obtained using the same raw materials, reagents, and production method as in Example 6, except that 2,3,4,6-O-tetrabenzyl-1-(pyridin-1-yl)sulfonyl-β-D-thioglucuronopyranoside was used instead of 2,3,4,6-O-tetrabenzyl-1-(pyridin-1-yl)sulfonyl-β-D-thioglucuronopyranoside. 1H NMR (500 MHz, MeOD) δ 5.28 (s, 1H), 4.16 (s, 1H), 3.79 (d, J = 2.0 Hz, 2H), 3.46 (dd, J = 20.4, 9.3 Hz, 2H), 3.38 (s, 1H), 3.35 - 3.31 (m, 1H), 3.23 (d, J = 9.5 Hz, 1H), 3.11 (d, J = 9.5 Hz, 1H), 2.88 (dd, J = 13.5, 3.0 Hz, 1H), 2.03 (dd, J = 13.5, 10.3 Hz, 1H), 1.93 (d, J = 7.1Hz, 2H), 1.86 - 1.05 (m, 21H), 1.06 - 0.93 (m, 12H), 0.90 - 0.82 (m, 6H), 0.81 (d, J = 11.4 Hz, 1H). LRMS (ESI):629.41 [MH] - .

[0103] Example 28 (3R,5S,8R,9R,10S,14R,17R,18S)-Oleanolic acid 3-methyl-β-D-glucuronopyranoside (A28) The remaining raw materials, reagents, and preparation method were the same as in Example 6, but with the exception of 2,3,4,6-O-tetrabenzyl-1-(pyridin-1-yl)sulfonyl-β-D-thioglucopyranoside being replaced with 2,3,4,6-O-tetrabenzyl-1-(pyridin-1-yl)sulfonyl-β-D-thioglucuronopyranoside, and (3S,5S,8R,9R,10S,14R,17R,18S)-28-O-benzyl-3-aldehyde oleanolic acid being replaced with (3R,5S,8R,9R,10S,14R,17R,18S)-28-O-benzyl-3-aldehyde oleanolic acid. A28 (yield 65%) was obtained using the same method as in Example 6, using the same starting materials, reagents, and preparation method as in Example 6. 1H NMR (500 MHz, MeOD) δ 5.28 (s, 1H), 4.16 (s, 1H), 3.79 (d, J = 2.0 Hz, 2H), 3.46 (dd, J = 20.4, 9.3 Hz, 2H), 3.38 (s, 1H), 3.35 - 3.31 (m, 1H), 3.23 (d, J = 9.5 Hz, 1H), 3.11 (d, J = 9.5 Hz, 1H), 2.88 (dd, J = 13.5, 3.0 Hz, 1H), 2.03 (dd, J = 13.5, 10.3 Hz, 1H), 1.93 (d, J = 7.1Hz, 2H), 1.86 - 1.05 (m, 21H), 1.06 - 0.93 (m, 12H), 0.90 - 0.82 (m, 6H), 0.81 (d, J = 11.4 Hz, 1H). LRMS (ESI):629.41 [MH] - .

[0104] Example 29 (3S,5S,8R,9R,10S,14R,17R,18S)-Oleanolic acid-3-carbonyl-β-D-glucuronopyranoside (A29) Except for changing 2,3,4,6-O-tetrabenzyl-1-(pyridin-1-yl)sulfonyl-β-D-thioglucuronopyranoside to 2,3,4,6-O-tetrabenzyl-1-(pyridin-1-yl)sulfonyl-β-D-thioglucuronopyranoside, the remaining raw materials, reagents, and production method were the same as in Example 10, and A29 (yield 89%) was obtained. 1H NMR (500 MHz, MeOD) δ 5.28 (s, 1H), 4.16 (s, 1H), 3.79 (d, J = 2.0 Hz, 2H), 3.46 (dd, J = 20.4, 9.3 Hz, 2H), 3.38 (s, 1H), 3.35 - 3.31 (m, 1H), 3.23 (d, J = 9.5 Hz, 1H), 3.11 (d, J = 9.5 Hz, 1H), 2.88 (dd, J = 13.5, 3.0 Hz, 1H), 2.03 (dd, J = 13.5, 10.3 Hz, 1H), 1.93 (d, J = 7.1Hz, 2H), 1.86 - 1.05 (m, 21H), 1.06 - 0.93 (m, 12H), 0.90 - 0.82 (m, 6H), 0.81 (d, J = 11.4 Hz, 1H). LRMS (ESI):643.39 [MH] - .

[0105] Example 30 (3R,5S,8R,9R,10S,14R,17R,18S)-Oleanolic acid 3-carbonyl-β-D-glucuronopyranoside (A30) The remaining raw materials, reagents, and preparation method were the same as in Example 10, but with the exception of 2,3,4,6-O-tetrabenzyl-1-(pyridin-1-yl)sulfonyl-β-D-thioglucopyranoside being replaced with 2,3,4,6-O-tetrabenzyl-1-(pyridin-1-yl)sulfonyl-β-D-thioglucuronopyranoside, and (3S,5S,8R,9R,10S,14R,17R,18S)-28-O-benzyl-3-aldehyde oleanolic acid being replaced with (3R,5S,8R,9R,10S,14R,17R,18S)-28-O-benzyl-3-aldehyde oleanolic acid. A30 (yield 88%) was obtained using the same method as in Example 10. 1H NMR (500 MHz, MeOD) δ 5.28 (s, 1H), 4.16 (s, 1H), 3.79 (d, J = 2.0 Hz, 2H), 3.46 (dd, J = 20.4, 9.3 Hz, 2H), 3.38 (s, 1H), 3.35 - 3.31 (m, 1H), 3.23 (d, J = 9.5 Hz, 1H), 3.11 (d, J = 9.5 Hz, 1H), 2.88 (dd, J = 13.5, 3.0 Hz, 1H), 2.03 (dd, J = 13.5, 10.3 Hz, 1H), 1.93 (d, J = 7.1Hz, 2H), 1.86 - 1.05 (m, 21H), 1.06 - 0.93 (m, 12H), 0.90 - 0.82 (m, 6H), 0.81 (d, J = 11.4 Hz, 1H). LRMS (ESI):643.39 [MH] - .

[0106] Example 31 (3S,5S,8R,9R,10S,14R,17R,18S)-oleanolic acid-3-(1'R)-(hydroxy)methyl-6''-deoxy-β-D-glucopyranoside (A31) The remaining raw materials, reagents, and production method were the same as in Example 2, except that 2,3,4,6-O-tetrabenzyl-1-(pyridin-1-yl)sulfonyl-β-D-thioglucopyranoside was replaced with 2,3,4,6-O-tetrabenzyl-1-(pyridin-1-yl)sulfonyl-6-deoxy-β-D-thioglucopyranoside. A31 (yield 67%) was obtained using the same method as in Example 2. 1H NMR (500 MHz, MeOD) δ 5.28 (s, 1H), 4.16 (s, 1H), 3.79 (d, J = 2.0 Hz, 2H), 3.46 (dd, J = 20.4, 9.3 Hz, 2H), 3.38 (s, 1H), 3.35 - 3.31 (m, 1H), 3.23 (d, J = 9.5 Hz, 1H), 3.11 (d, J = 9.5 Hz, 1H), 2.88 (dd, J = 13.5, 3.0 Hz, 1H), 2.03 (dd, J = 13.5, 10.3 Hz, 1H), 1.93 (d, J = 7.1Hz, 2H), 1.86 - 1.05 (m, 21H), 1.06 - 0.93 (m, 12H), 0.90 - 0.82 (m, 6H), 0.81 (d, J = 11.4 Hz, 1H). LRMS (ESI):615.43 [MH] - .

[0107] Example 32 (3R,5S,8R,9R,10S,14R,17R,18S)-oleanolic acid-3-(1'R)-(hydroxy)methyl-6''-deoxy-β-D-glucopyranoside (A32) The remaining raw materials, reagents, and production method were the same as in Example 2, but with the exception of 2,3,4,6-O-tetrabenzyl-1-(pyridin-1-yl)sulfonyl-β-D-thioglucopyranoside being replaced with 2,3,4,6-O-tetrabenzyl-1-(pyridin-1-yl)sulfonyl-6-deoxy-β-D-thioglucopyranoside, and (3S,5S,8R,9R,10S,14R,17R,18S)-28-O-benzyl-3-aldehyde oleanolic acid being replaced with (3R,5S,8R,9R,10S,14R,17R,18S)-28-O-benzyl-3-aldehyde oleanolic acid. A32 (yield 78%) was obtained using the same method as in Example 2. 1H NMR (500 MHz, MeOD) δ 5.28 (s, 1H), 4.16 (s, 1H), 3.79 (d, J = 2.0 Hz, 2H), 3.46 (dd, J = 20.4, 9.3 Hz, 2H), 3.38 (s, 1H), 3.35 - 3.31 (m, 1H), 3.23 (d, J = 9.5 Hz, 1H), 3.11 (d, J = 9.5 Hz, 1H), 2.88 (dd, J = 13.5, 3.0 Hz, 1H), 2.03 (dd, J = 13.5, 10.3 Hz, 1H), 1.93 (d, J = 7.1Hz, 2H), 1.86 - 1.05 (m, 21H), 1.06 - 0.93 (m, 12H), 0.90 - 0.82 (m, 6H), 0.81 (d, J = 11.4 Hz, 1H). LRMS (ESI):615.43 [MH] - .

[0108] Example 33 (3S,5S,8R,9R,10S,14R,17R,18S)-oleanolic acid-3-methyl-6″-deoxy-β-D-glucopyranoside (A33) A33 (yield 68%) was obtained using the same raw materials, reagents, and production method as in Example 6, except that 2,3,4,6-O-tetrabenzyl-1-(pyridin-1-yl)sulfonyl-β-D-thioglucopyranoside was used instead of 2,3,4,6-O-tetrabenzyl-1-(pyridin-1-yl)sulfonyl-6-deoxy-β-D-thioglucopyranoside. 1H NMR (500 MHz, MeOD) δ 5.28 (s, 1H), 4.16 (s, 1H), 3.79 (d, J = 2.0 Hz, 2H), 3.46 (dd, J = 20.4, 9.3 Hz, 2H), 3.38 (s, 1H), 3.35 - 3.31 (m, 1H), 3.23 (d, J = 9.5 Hz, 1H), 3.11 (d, J = 9.5 Hz, 1H), 2.88 (dd, J = 13.5, 3.0 Hz, 1H), 2.03 (dd, J = 13.5, 10.3 Hz, 1H), 1.93 (d, J = 7.1Hz, 2H), 1.86 - 1.05 (m, 21H), 1.06 - 0.93 (m, 12H), 0.90 - 0.82 (m, 6H), 0.81 (d, J = 11.4 Hz, 1H). LRMS (ESI):599.44 [MH] - .

[0109] Example 34 (3R,5S,8R,9R,10S,14R,17R,18S)-Oleanolic acid-3-methyl-6″-deoxy-β-D-glucopyranoside (A34) The remaining raw materials, reagents, and preparation method were the same as in Example 6, but with the exception of 2,3,4,6-O-tetrabenzyl-1-(pyridin-1-yl)sulfonyl-β-D-thioglucopyranoside being replaced with 2,3,4,6-O-tetrabenzyl-1-(pyridin-1-yl)sulfonyl-6-deoxy-β-D-thioglucopyranoside, and (3S,5S,8R,9R,10S,14R,17R,18S)-28-O-benzyl-3-aldehyde oleanolic acid being replaced with (3R,5S,8R,9R,10S,14R,17R,18S)-28-O-benzyl-3-aldehyde oleanolic acid. A34 (yield 65%) was obtained using the same method as in Example 6. 1H NMR (500 MHz, MeOD) δ 5.28 (s, 1H), 4.16 (s, 1H), 3.79 (d, J = 2.0 Hz, 2H), 3.46 (dd, J = 20.4, 9.3 Hz, 2H), 3.38 (s, 1H), 3.35 - 3.31 (m, 1H), 3.23 (d, J = 9.5 Hz, 1H), 3.11 (d, J = 9.5 Hz, 1H), 2.88 (dd, J = 13.5, 3.0 Hz, 1H), 2.03 (dd, J = 13.5, 10.3 Hz, 1H), 1.93 (d, J = 7.1Hz, 2H), 1.86 - 1.05 (m, 21H), 1.06 - 0.93 (m, 12H), 0.90 - 0.82 (m, 6H), 0.81 (d, J = 11.4 Hz, 1H). LRMS (ESI):599.44 [MH] - .

[0110] Example 35 (3S,5S,8R,9R,10S,14R,17R,18S)-Oleanolic acid-3-carbonyl-6″-deoxy-β-D-glucopyranoside (A35) The remaining raw materials, reagents and production method were the same as in Example 10, except that 2,3,4,6-O-tetrabenzyl-1-(pyridin-1-yl)sulfonyl-β-D-thioglucopyranoside was replaced with 2,3,4,6-O-tetrabenzyl-1-(pyridin-1-yl)sulfonyl-6-deoxy-β-D-thioglucopyranoside, and A35 (yield 86%) was obtained. 1H NMR (500 MHz, MeOD) δ 5.28 (s, 1H), 4.16 (s, 1H), 3.79 (d, J = 2.0 Hz, 2H), 3.46 (dd, J = 20.4, 9.3 Hz, 2H), 3.38 (s, 1H), 3.35 - 3.31 (m, 1H), 3.23 (d, J = 9.5 Hz, 1H), 3.11 (d, J = 9.5 Hz, 1H), 2.88 (dd, J = 13.5, 3.0 Hz, 1H), 2.03 (dd, J = 13.5, 10.3 Hz, 1H), 1.93 (d, J = 7.1Hz, 2H), 1.86 - 1.05 (m, 21H), 1.06 - 0.93 (m, 12H), 0.90 - 0.82 (m, 6H), 0.81 (d, J = 11.4 Hz, 1H). LRMS (ESI):613.42 [MH] - .

[0111] Example 36 (3R,5S,8R,9R,10S,14R,17R,18S)-Oleanolic acid 3-carbonyl-6″-deoxy-β-D-glucopyranoside (A36) The remaining raw materials, reagents, and preparation method were the same as in Example 10, but with the exception of 2,3,4,6-O-tetrabenzyl-1-(pyridin-1-yl)sulfonyl-β-D-thioglucopyranoside being replaced with 2,3,4,6-O-tetrabenzyl-1-(pyridin-1-yl)sulfonyl-6-deoxy-β-D-thioglucopyranoside, and (3S,5S,8R,9R,10S,14R,17R,18S)-28-O-benzyl-3-aldehyde oleanolic acid being replaced with (3R,5S,8R,9R,10S,14R,17R,18S)-28-O-benzyl-3-aldehyde oleanolic acid. A36 (yield 85%) was obtained using the same method as in Example 10. 1H NMR (500 MHz, MeOD) δ 5.28 (s, 1H), 4.16 (s, 1H), 3.79 (d, J = 2.0 Hz, 2H), 3.46 (dd, J = 20.4, 9.3 Hz, 2H), 3.38 (s, 1H), 3.35 - 3.31 (m, 1H), 3.23 (d, J = 9.5 Hz, 1H), 3.11 (d, J = 9.5 Hz, 1H), 2.88 (dd, J = 13.5, 3.0 Hz, 1H), 2.03 (dd, J = 13.5, 10.3 Hz, 1H), 1.93 (d, J = 7.1Hz, 2H), 1.86 - 1.05 (m, 21H), 1.06 - 0.93 (m, 12H), 0.90 - 0.82 (m, 6H), 0.81 (d, J = 11.4 Hz, 1H). LRMS (ESI):613.42 [MH] - .

[0112] Example 37 (3S,5S,8R,9R,10S,14R,17R,18S)-Oleanolic acid-3-(1'R)-(hydroxy)methyl-β-D-xylopyranoside (A37) The remaining raw materials, reagents, and production method were the same as in Example 2, except that 2,3,4,6-O-tetrabenzyl-1-(pyridin-1-yl)sulfonyl-β-D-thioglucopyranoside was replaced with 2,3,4,6-O-tetrabenzyl-1-(pyridin-1-yl)sulfonyl-β-D-thioxilopyranoside. A37 (yield 77%) was obtained using the same procedure as in Example 2. 1H NMR (500 MHz, MeOD) δ 5.28 (s, 1H), 4.16 (s, 1H), 3.79 (d, J = 2.0 Hz, 2H), 3.46 (dd, J = 20.4, 9.3 Hz, 2H), 3.38 (s, 1H), 3.35 - 3.31 (m, 1H), 3.23 (d, J = 9.5 Hz, 1H), 3.11 (d, J = 9.5 Hz, 1H), 2.88 (dd, J = 13.5, 3.0 Hz, 1H), 2.03 (dd, J = 13.5, 10.3 Hz, 1H), 1.93 (d, J = 7.1Hz, 2H), 1.86 - 1.05 (m, 21H), 1.06 - 0.93 (m, 12H), 0.90 - 0.82 (m, 6H), 0.81 (d, J = 11.4 Hz, 1H). LRMS (ESI):601.42 [MH] - .

[0113] Example 38 (3R,5S,8R,9R,10S,14R,17R,18S)-Oleanolic acid-3-(1'R)-(hydroxy)methyl-β-D-xylopyranoside (A38) The remaining raw materials, reagents, and production method were the same as in Example 2, but with the exception of 2,3,4,6-O-tetrabenzyl-1-(pyridin-1-yl)sulfonyl-β-D-thioglucopyranoside being replaced with 2,3,4,6-O-tetrabenzyl-1-(pyridin-1-yl)sulfonyl-β-D-thioxilopyranoside, and (3S,5S,8R,9R,10S,14R,17R,18S)-28-O-benzyl-3-aldehyde oleanolic acid being replaced with (3R,5S,8R,9R,10S,14R,17R,18S)-28-O-benzyl-3-aldehyde oleanolic acid. A38 (yield 78%) was obtained using the same method as in Example 2. 1H NMR (500 MHz, MeOD) δ 5.28 (s, 1H), 4.16 (s, 1H), 3.79 (d, J = 2.0 Hz, 2H), 3.46 (dd, J = 20.4, 9.3 Hz, 2H), 3.38 (s, 1H), 3.35 - 3.31 (m, 1H), 3.23 (d, J = 9.5 Hz, 1H), 3.11 (d, J = 9.5 Hz, 1H), 2.88 (dd, J = 13.5, 3.0 Hz, 1H), 2.03 (dd, J = 13.5, 10.3 Hz, 1H), 1.93 (d, J = 7.1Hz, 2H), 1.86 - 1.05 (m, 21H), 1.06 - 0.93 (m, 12H), 0.90 - 0.82 (m, 6H), 0.81 (d, J = 11.4 Hz, 1H). LRMS (ESI):601.42 [MH] - .

[0114] Example 39 (3S,5S,8R,9R,10S,14R,17R,18S)-oleanolic acid 3-methyl-β-D-xylopyranoside (A39) A39 (yield 69%) was obtained using the same raw materials, reagents, and production method as in Example 6, except that 2,3,4,6-O-tetrabenzyl-1-(pyridin-1-yl)sulfonyl-β-D-thioglucopyranoside was used instead of 2,3,4,6-O-tetrabenzyl-1-(pyridin-1-yl)sulfonyl-β-D-thioxilopyranoside. 1H NMR (500 MHz, MeOD) δ 5.28 (s, 1H), 4.16 (s, 1H), 3.79 (d, J = 2.0 Hz, 2H), 3.46 (dd, J = 20.4, 9.3 Hz, 2H), 3.38 (s, 1H), 3.35 - 3.31 (m, 1H), 3.23 (d, J = 9.5 Hz, 1H), 3.11 (d, J = 9.5 Hz, 1H), 2.88 (dd, J = 13.5, 3.0 Hz, 1H), 2.03 (dd, J = 13.5, 10.3 Hz, 1H), 1.93 (d, J = 7.1Hz, 2H), 1.86 - 1.05 (m, 21H), 1.06 - 0.93 (m, 12H), 0.90 - 0.82 (m, 6H), 0.81 (d, J = 11.4 Hz, 1H). LRMS (ESI):585.42 [MH] - .

[0115] Example 40 (3R,5S,8R,9R,10S,14R,17R,18S)-oleanolic acid 3-methyl-β-D-xylopyranoside (A40) The remaining raw materials, reagents, and preparation methods were the same as in Example 6, but with the exception of 2,3,4,6-O-tetrabenzyl-1-(pyridin-1-yl)sulfonyl-β-D-thioglucopyranoside, which was replaced with 2,3,4,6-O-tetrabenzyl-1-(pyridin-1-yl)sulfonyl-β-D-thioxilopyranoside, and (3S,5S,8R,9R,10S,14R,17R,18S)-28-O-benzyl-3-aldehyde oleanolic acid, which was replaced with (3R,5S,8R,9R,10S,14R,17R,18S)-28-O-benzyl-3-aldehyde oleanolic acid. A40 (yield 66%) was obtained using the same procedures as in Example 6. 1H NMR (500 MHz, MeOD) δ 5.28 (s, 1H), 4.16 (s, 1H), 3.79 (d, J = 2.0 Hz, 2H), 3.46 (dd, J = 20.4, 9.3 Hz, 2H), 3.38 (s, 1H), 3.35 - 3.31 (m, 1H), 3.23 (d, J = 9.5 Hz, 1H), 3.11 (d, J = 9.5 Hz, 1H), 2.88 (dd, J = 13.5, 3.0 Hz, 1H), 2.03 (dd, J = 13.5, 10.3 Hz, 1H), 1.93 (d, J = 7.1Hz, 2H), 1.86 - 1.05 (m, 21H), 1.06 - 0.93 (m, 12H), 0.90 - 0.82 (m, 6H), 0.81 (d, J = 11.4 Hz, 1H). LRMS (ESI):585.42 [MH] - .

[0116] Example 41 (3S,5S,8R,9R,10S,14R,17R,18S)-oleanolic acid-3-carbonyl-β-D-xylopyranoside (A41) The remaining raw materials, reagents and production method were the same as in Example 10, except that 2,3,4,6-O-tetrabenzyl-1-(pyridin-1-yl)sulfonyl-β-D-thioglucopyranoside was replaced with 2,3,4,6-O-tetrabenzyl-1-(pyridin-1-yl)sulfonyl-β-D-thioxilopyranoside, and A41 (yield 88%) was obtained. 1H NMR (500 MHz, MeOD) δ 5.28 (s, 1H), 4.16 (s, 1H), 3.79 (d, J = 2.0 Hz, 2H), 3.46 (dd, J = 20.4, 9.3 Hz, 2H), 3.38 (s, 1H), 3.35 - 3.31 (m, 1H), 3.23 (d, J = 9.5 Hz, 1H), 3.11 (d, J = 9.5 Hz, 1H), 2.88 (dd, J = 13.5, 3.0 Hz, 1H), 2.03 (dd, J = 13.5, 10.3 Hz, 1H), 1.93 (d, J = 7.1Hz, 2H), 1.86 - 1.05 (m, 21H), 1.06 - 0.93 (m, 12H), 0.90 - 0.82 (m, 6H), 0.81 (d, J = 11.4 Hz, 1H). LRMS (ESI):599.40 [MH] - .

[0117] Example 42 (3R,5S,8R,9R,10S,14R,17R,18S)-oleanolic acid 3-carbonyl-β-D-xylopyranoside (A42) The remaining raw materials, reagents, and preparation methods were the same as in Example 10, but with the exception of 2,3,4,6-O-tetrabenzyl-1-(pyridin-1-yl)sulfonyl-β-D-thioglucopyranoside, which was replaced with 2,3,4,6-O-tetrabenzyl-1-(pyridin-1-yl)sulfonyl-β-D-thioxilopyranoside, and (3S,5S,8R,9R,10S,14R,17R,18S)-28-O-benzyl-3-aldehyde oleanolic acid, which was replaced with (3R,5S,8R,9R,10S,14R,17R,18S)-28-O-benzyl-3-aldehyde oleanolic acid. A42 (yield 81%) was obtained using the same method as in Example 10. 1H NMR (500 MHz, MeOD) δ 5.28 (s, 1H), 4.16 (s, 1H), 3.79 (d, J = 2.0 Hz, 2H), 3.46 (dd, J = 20.4, 9.3 Hz, 2H), 3.38 (s, 1H), 3.35 - 3.31 (m, 1H), 3.23 (d, J = 9.5 Hz, 1H), 3.11 (d, J = 9.5 Hz, 1H), 2.88 (dd, J = 13.5, 3.0 Hz, 1H), 2.03 (dd, J = 13.5, 10.3 Hz, 1H), 1.93 (d, J = 7.1Hz, 2H), 1.86 - 1.05 (m, 21H), 1.06 - 0.93 (m, 12H), 0.90 - 0.82 (m, 6H), 0.81 (d, J = 11.4 Hz, 1H). LRMS (ESI):599.40 [MH] - .

[0118] Example 43 (3S,5S,8R,9R,10S,14R,17R,18S)-Oleanolic acid-3-(1'S)-(hydroxy)methyl-α-L-rhamnopyranoside (A43) The remaining raw materials, reagents, and production method were the same as in Example 2, except that 2,3,4,6-O-tetrabenzyl-1-(pyridin-1-yl)sulfonyl-β-D-thioglucopyranoside was replaced with 2,3,4,6-O-tetrabenzyl-1-(pyridin-1-yl)sulfonyl-α-D-thiorhamnopyranoside. A43 (yield 75%) was obtained using the same method as in Example 2. 1H NMR (500 MHz, MeOD) δ 5.28 (s, 1H), 4.16 (s, 1H), 3.79 (d, J = 2.0 Hz, 2H), 3.46 (dd, J = 20.4, 9.3 Hz, 2H), 3.38 (s, 1H), 3.35 - 3.31 (m, 1H), 3.23 (d, J = 9.5 Hz, 1H), 3.11 (d, J = 9.5 Hz, 1H), 2.88 (dd, J = 13.5, 3.0 Hz, 1H), 2.03 (dd, J = 13.5, 10.3 Hz, 1H), 1.93 (d, J = 7.1Hz, 2H), 1.86 - 1.05 (m, 21H), 1.06 - 0.93 (m, 12H), 0.90 - 0.82 (m, 6H), 0.81 (d, J = 11.4 Hz, 1H). LRMS (ESI):615.43 [MH] - .

[0119] Example 44 (3R,5S,8R,9R,10S,14R,17R,18S)-Oleanolic acid-3-(1'S)-(hydroxy)methyl-α-L-rhamnopyranoside (A44) The remaining raw materials, reagents, and production method were the same as in Example 2, but with the exception of 2,3,4,6-O-tetrabenzyl-1-(pyridin-1-yl)sulfonyl-β-D-thioglucopyranoside being replaced with 2,3,4,6-O-tetrabenzyl-1-(pyridin-1-yl)sulfonyl-α-D-thiorhamnopyranoside, and (3S,5S,8R,9R,10S,14R,17R,18S)-28-O-benzyl-3-aldehyde oleanolic acid being replaced with (3R,5S,8R,9R,10S,14R,17R,18S)-28-O-benzyl-3-aldehyde oleanolic acid. A44 (71% yield) was obtained using the same method as in Example 2, using the same raw materials, reagents, and production method as in Example 2. 1H NMR (500 MHz, MeOD) δ 5.28 (s, 1H), 4.16 (s, 1H), 3.79 (d, J = 2.0 Hz, 2H), 3.46 (dd, J = 20.4, 9.3 Hz, 2H), 3.38 (s, 1H), 3.35 - 3.31 (m, 1H), 3.23 (d, J = 9.5 Hz, 1H), 3.11 (d, J = 9.5 Hz, 1H), 2.88 (dd, J = 13.5, 3.0 Hz, 1H), 2.03 (dd, J = 13.5, 10.3 Hz, 1H), 1.93 (d, J = 7.1Hz, 2H), 1.86 - 1.05 (m, 21H), 1.06 - 0.93 (m, 12H), 0.90 - 0.82 (m, 6H), 0.81 (d, J = 11.4 Hz, 1H). LRMS (ESI):615.43 [MH] - .

[0120] Example 45 (3S,5S,8R,9R,10S,14R,17R,18S)-oleanolic acid-3-(1'S)-methyl-α-L-rhamnopyranoside (A45) A45 (yield 68%) was obtained using the same raw materials, reagents, and production method as in Example 6, except that 2,3,4,6-O-tetrabenzyl-1-(pyridin-1-yl)sulfonyl-β-D-thioglucopyranoside was replaced with 2,3,4,6-O-tetrabenzyl-1-(pyridin-1-yl)sulfonyl-α-D-thiorhamnopyranoside. 1H NMR (500 MHz, MeOD) δ 5.28 (s, 1H), 4.16 (s, 1H), 3.79 (d, J = 2.0 Hz, 2H), 3.46 (dd, J = 20.4, 9.3 Hz, 2H), 3.38 (s, 1H), 3.35 - 3.31 (m, 1H), 3.23 (d, J = 9.5 Hz, 1H), 3.11 (d, J = 9.5 Hz, 1H), 2.88 (dd, J = 13.5, 3.0 Hz, 1H), 2.03 (dd, J = 13.5, 10.3 Hz, 1H), 1.93 (d, J = 7.1Hz, 2H), 1.86 - 1.05 (m, 21H), 1.06 - 0.93 (m, 12H), 0.90 - 0.82 (m, 6H), 0.81 (d, J = 11.4 Hz, 1H). LRMS (ESI):599.44 [MH] - .

[0121] Example 46 (3R,5S,8R,9R,10S,14R,17R,18S)-oleanolic acid-3-(1'S)-methyl-α-L-rhamnopyranoside (A46) The remaining raw materials, reagents, and preparation method were the same as in Example 6, but with the exception of 2,3,4,6-O-tetrabenzyl-1-(pyridin-1-yl)sulfonyl-β-D-thioglucopyranoside being replaced with 2,3,4,6-O-tetrabenzyl-1-(pyridin-1-yl)sulfonyl-α-D-thiorhamnopyranoside, and (3S,5S,8R,9R,10S,14R,17R,18S)-28-O-benzyl-3-aldehyde oleanolic acid being replaced with (3R,5S,8R,9R,10S,14R,17R,18S)-28-O-benzyl-3-aldehyde oleanolic acid. A46 (yield 66%) was obtained using the same method as in Example 6. 1H NMR (500 MHz, MeOD) δ 5.28 (s, 1H), 4.16 (s, 1H), 3.79 (d, J = 2.0 Hz, 2H), 3.46 (dd, J = 20.4, 9.3 Hz, 2H), 3.38 (s, 1H), 3.35 - 3.31 (m, 1H), 3.23 (d, J = 9.5 Hz, 1H), 3.11 (d, J = 9.5 Hz, 1H), 2.88 (dd, J = 13.5, 3.0 Hz, 1H), 2.03 (dd, J = 13.5, 10.3 Hz, 1H), 1.93 (d, J = 7.1Hz, 2H), 1.86 - 1.05 (m, 21H), 1.06 - 0.93 (m, 12H), 0.90 - 0.82 (m, 6H), 0.81 (d, J = 11.4 Hz, 1H). LRMS (ESI):599.44 [MH] - .

[0122] Example 47 (3S,5S,8R,9R,10S,14R,17R,18S)-oleanolic acid-3-(1'S)-carbonyl-α-L-rhamnopyranoside (A47) A47 (yield 84%) was obtained using the same raw materials, reagents, and production method as in Example 10, except that 2,3,4,6-O-tetrabenzyl-1-(pyridin-1-yl)sulfonyl-β-D-thioglucopyranoside was replaced with 2,3,4,6-O-tetrabenzyl-1-(pyridin-1-yl)sulfonyl-α-D-thiorhamnopyranoside. 1H NMR (500 MHz, MeOD) δ 5.28 (s, 1H), 4.16 (s, 1H), 3.79 (d, J = 2.0 Hz, 2H), 3.46 (dd, J = 20.4, 9.3 Hz, 2H), 3.38 (s, 1H), 3.35 - 3.31 (m, 1H), 3.23 (d, J = 9.5 Hz, 1H), 3.11 (d, J = 9.5 Hz, 1H), 2.88 (dd, J = 13.5, 3.0 Hz, 1H), 2.03 (dd, J = 13.5, 10.3 Hz, 1H), 1.93 (d, J = 7.1Hz, 2H), 1.86 - 1.05 (m, 21H), 1.06 - 0.93 (m, 12H), 0.90 - 0.82 (m, 6H), 0.81 (d, J = 11.4 Hz, 1H). LRMS (ESI):613.42 [MH] - .

[0123] Example 48 (3R,5S,8R,9R,10S,14R,17R,18S)-oleanolic acid-3-(1'S)-carbonyl-α-L-rhamnopyranoside (A48) The remaining raw materials, reagents, and preparation method were the same as in Example 10, but A48 (yield 87%) was obtained. 1H NMR (500 MHz, MeOD) δ 5.28 (s, 1H), 4.16 (s, 1H), 3.79 (d, J = 2.0 Hz, 2H), 3.46 (dd, J = 20.4, 9.3 Hz, 2H), 3.38 (s, 1H), 3.35 - 3.31 (m, 1H), 3.23 (d, J = 9.5 Hz, 1H), 3.11 (d, J = 9.5 Hz, 1H), 2.88 (dd, J = 13.5, 3.0 Hz, 1H), 2.03 (dd, J = 13.5, 10.3 Hz, 1H), 1.93 (d, J = 7.1Hz, 2H), 1.86 - 1.05 (m, 21H), 1.06 - 0.93 (m, 12H), 0.90 - 0.82 (m, 6H), 0.81 (d, J = 11.4 Hz, 1H). LRMS (ESI):613.42 [MH] - .

[0124] Example 49 (3S,5S,8R,9R,10S,14R,17R,18S)-oleanolic acid-3-(1'S)-(hydroxy)methyl-α-L-fucopyranoside (A49) The remaining raw materials, reagents, and production method were the same as in Example 2, except that 2,3,4,6-O-tetrabenzyl-1-(pyridin-1-yl)sulfonyl-β-D-thioglucopyranoside was used instead of 2,3,4,6-O-tetrabenzyl-1-(pyridin-1-yl)sulfonyl-β-D-thiofcopyranoside. A49 (yield 72%) was obtained using the same method as in Example 2. 1H NMR (500 MHz, MeOD) δ 5.28 (s, 1H), 4.16 (s, 1H), 3.79 (d, J = 2.0 Hz, 2H), 3.46 (dd, J = 20.4, 9.3 Hz, 2H), 3.38 (s, 1H), 3.35 - 3.31 (m, 1H), 3.23 (d, J = 9.5 Hz, 1H), 3.11 (d, J = 9.5 Hz, 1H), 2.88 (dd, J = 13.5, 3.0 Hz, 1H), 2.03 (dd, J = 13.5, 10.3 Hz, 1H), 1.93 (d, J = 7.1Hz, 2H), 1.86 - 1.05 (m, 21H), 1.06 - 0.93 (m, 12H), 0.90 - 0.82 (m, 6H), 0.81 (d, J = 11.4 Hz, 1H). LRMS (ESI):615.43 [MH] - .

[0125] Example 50 (3R,5S,8R,9R,10S,14R,17R,18S)-oleanolic acid-3-(1'S)-(hydroxy)methyl-α-L-fucopyranoside (A50) The remaining raw materials, reagents, and production method were the same as in Example 2, but with the exception of 2,3,4,6-O-tetrabenzyl-1-(pyridin-1-yl)sulfonyl-β-D-thioglucopyranoside being replaced with 2,3,4,6-O-tetrabenzyl-1-(pyridin-1-yl)sulfonyl-β-D-thiofcopyranoside, and (3S,5S,8R,9R,10S,14R,17R,18S)-28-O-benzyl-3-aldehyde oleanolic acid being replaced with (3R,5S,8R,9R,10S,14R,17R,18S)-28-O-benzyl-3-aldehyde oleanolic acid. A50 (yield 71%) was obtained using the same method as in Example 2. 1H NMR (500 MHz, MeOD) δ 5.28 (s, 1H), 4.16 (s, 1H), 3.79 (d, J = 2.0 Hz, 2H), 3.46 (dd, J = 20.4, 9.3 Hz, 2H), 3.38 (s, 1H), 3.35 - 3.31 (m, 1H), 3.23 (d, J = 9.5 Hz, 1H), 3.11 (d, J = 9.5 Hz, 1H), 2.88 (dd, J = 13.5, 3.0 Hz, 1H), 2.03 (dd, J = 13.5, 10.3 Hz, 1H), 1.93 (d, J = 7.1Hz, 2H), 1.86 - 1.05 (m, 21H), 1.06 - 0.93 (m, 12H), 0.90 - 0.82 (m, 6H), 0.81 (d, J = 11.4 Hz, 1H). LRMS (ESI):615.43 [MH] - .

[0126] Example 51 (3S,5S,8R,9R,10S,14R,17R,18S)-oleanolic acid-3-(1'S)-methyl-α-L-fucopyranoside (A51) The remaining raw materials, reagents, and production method were the same as in Example 6, except that 2,3,4,6-O-tetrabenzyl-1-(pyridin-1-yl)sulfonyl-β-D-thioglucopyranoside was used instead of 2,3,4,6-O-tetrabenzyl-1-(pyridin-1-yl)sulfonyl-β-D-thiofcopyranoside. A51 (yield 69%) was obtained. 1H NMR (500 MHz, MeOD) δ 5.28 (s, 1H), 4.16 (s, 1H), 3.79 (d, J = 2.0 Hz, 2H), 3.46 (dd, J = 20.4, 9.3 Hz, 2H), 3.38 (s, 1H), 3.35 - 3.31 (m, 1H), 3.23 (d, J = 9.5 Hz, 1H), 3.11 (d, J = 9.5 Hz, 1H), 2.88 (dd, J = 13.5, 3.0 Hz, 1H), 2.03 (dd, J = 13.5, 10.3 Hz, 1H), 1.93 (d, J = 7.1Hz, 2H), 1.86 - 1.05 (m, 21H), 1.06 - 0.93 (m, 12H), 0.90 - 0.82 (m, 6H), 0.81 (d, J = 11.4 Hz, 1H). LRMS (ESI):599.44 [MH] - .

[0127] Example 52 (3R,5S,8R,9R,10S,14R,17R,18S)-oleanolic acid-3-(1'S)-methyl-α-L-fucopyranoside (A52) The remaining raw materials, reagents, and production method were the same as in Example 6, but with the exception of 2,3,4,6-O-tetrabenzyl-1-(pyridin-1-yl)sulfonyl-β-D-thioglucopyranoside being replaced with 2,3,4,6-O-tetrabenzyl-1-(pyridin-1-yl)sulfonyl-β-D-thiofcopyranoside, and (3S,5S,8R,9R,10S,14R,17R,18S)-28-O-benzyl-3-aldehyde oleanolic acid being replaced with (3R,5S,8R,9R,10S,14R,17R,18S)-28-O-benzyl-3-aldehyde oleanolic acid. A52 (yield 61%) was obtained using the same method as in Example 6. 1H NMR (500 MHz, MeOD) δ 5.28 (s, 1H), 4.16 (s, 1H), 3.79 (d, J = 2.0 Hz, 2H), 3.46 (dd, J = 20.4, 9.3 Hz, 2H), 3.38 (s, 1H), 3.35 - 3.31 (m, 1H), 3.23 (d, J = 9.5 Hz, 1H), 3.11 (d, J = 9.5 Hz, 1H), 2.88 (dd, J = 13.5, 3.0 Hz, 1H), 2.03 (dd, J = 13.5, 10.3 Hz, 1H), 1.93 (d, J = 7.1Hz, 2H), 1.86 - 1.05 (m, 21H), 1.06 - 0.93 (m, 12H), 0.90 - 0.82 (m, 6H), 0.81 (d, J = 11.4 Hz, 1H). LRMS (ESI):599.44 [MH] - .

[0128] Example 53 (3S,5S,8R,9R,10S,14R,17R,18S)-oleanolic acid-3-(1'S)-carbonyl-α-L-fucopyranoside (A53) A53 (yield 86%) was obtained using the same raw materials, reagents, and production method as in Example 10, except that 2,3,4,6-O-tetrabenzyl-1-(pyridin-1-yl)sulfonyl-β-D-thioglucopyranoside was used instead of 2,3,4,6-O-tetrabenzyl-1-(pyridin-1-yl)sulfonyl-β-D-thiofcopyranoside. 1H NMR (500 MHz, MeOD) δ 5.28 (s, 1H), 4.16 (s, 1H), 3.79 (d, J = 2.0 Hz, 2H), 3.46 (dd, J = 20.4, 9.3 Hz, 2H), 3.38 (s, 1H), 3.35 - 3.31 (m, 1H), 3.23 (d, J = 9.5 Hz, 1H), 3.11 (d, J = 9.5 Hz, 1H), 2.88 (dd, J = 13.5, 3.0 Hz, 1H), 2.03 (dd, J = 13.5, 10.3 Hz, 1H), 1.93 (d, J = 7.1Hz, 2H), 1.86 - 1.05 (m, 21H), 1.06 - 0.93 (m, 12H), 0.90 - 0.82 (m, 6H), 0.81 (d, J = 11.4 Hz, 1H). LRMS (ESI):613.42 [MH] - .

[0129] Example 54 (3R,5S,8R,9R,10S,14R,17R,18S)-oleanolic acid-3-(1'S)-carbonyl-α-L-fucopyranoside (A54) The remaining raw materials, reagents, and preparation method were the same as in Example 10, but with the exception of 2,3,4,6-O-tetrabenzyl-1-(pyridin-1-yl)sulfonyl-β-D-thioglucopyranoside being replaced with 2,3,4,6-O-tetrabenzyl-1-(pyridin-1-yl)sulfonyl-β-D-thiofcopyranoside, and (3S,5S,8R,9R,10S,14R,17R,18S)-28-O-benzyl-3-aldehyde oleanolic acid being replaced with (3R,5S,8R,9R,10S,14R,17R,18S)-28-O-benzyl-3-aldehyde oleanolic acid. A54 (yield 82%) was obtained using the same method as in Example 10. 1H NMR (500 MHz, MeOD) δ 5.28 (s, 1H), 4.16 (s, 1H), 3.79 (d, J = 2.0 Hz, 2H), 3.46 (dd, J = 20.4, 9.3 Hz, 2H), 3.38 (s, 1H), 3.35 - 3.31 (m, 1H), 3.23 (d, J = 9.5 Hz, 1H), 3.11 (d, J = 9.5 Hz, 1H), 2.88 (dd, J = 13.5, 3.0 Hz, 1H), 2.03 (dd, J = 13.5, 10.3 Hz, 1H), 1.93 (d, J = 7.1Hz, 2H), 1.86 - 1.05 (m, 21H), 1.06 - 0.93 (m, 12H), 0.90 - 0.82 (m, 6H), 0.81 (d, J = 11.4 Hz, 1H). LRMS (ESI):613.42 [MH] - .

[0130] Example 55 (3S,5S,8R,9R,10S,14R,17R,18S)-Oleanolic acid-3-(1'R)-(hydroxy)methyl-6''-deoxy-6''-fluoro-β-D-glucopyranoside (A55) The remaining raw materials, reagents, and production method were the same as in Example 2, except that 2,3,4,6-O-tetrabenzyl-1-(pyridin-1-yl)sulfonyl-β-D-thioglucopyranoside was replaced with 2,3,4,6-O-tetrabenzyl-1-(pyridin-1-yl)sulfonyl-6-deoxy-6-fluoro-β-D-thioglucopyranoside. A55 (yield 72%) was obtained using the same method as in Example 2. 1H NMR (500 MHz, MeOD) δ 5.28 (s, 1H), 4.16 (s, 1H), 3.79 (d, J = 2.0 Hz, 2H), 3.46 (dd, J = 20.4, 9.3 Hz, 2H), 3.38 (s, 1H), 3.35 - 3.31 (m, 1H), 3.23 (d, J = 9.5 Hz, 1H), 3.11 (d, J = 9.5 Hz, 1H), 2.88 (dd, J = 13.5, 3.0 Hz, 1H), 2.03 (dd, J = 13.5, 10.3 Hz, 1H), 1.93 (d, J = 7.1Hz, 2H), 1.86 - 1.05 (m, 21H), 1.06 - 0.93 (m, 12H), 0.90 - 0.82 (m, 6H), 0.81 (d, J = 11.4 Hz, 1H). LRMS (ESI):633.42 [MH] - .

[0131] Example 56 (3R,5S,8R,9R,10S,14R,17R,18S)-Oleanolic acid-3-(1'R)-(hydroxy)methyl-6''-deoxy-6''-fluoro-β-D-glucopyranoside (A56) The remaining raw materials, reagents, and production method were the same as in Example 2, but with the exception of 2,3,4,6-O-tetrabenzyl-1-(pyridin-1-yl)sulfonyl-β-D-thioglucopyranoside being replaced with 2,3,4,6-O-tetrabenzyl-1-(pyridin-1-yl)sulfonyl-6-deoxy-6-fluoro-β-D-thioglucopyranoside, and (3S,5S,8R,9R,10S,14R,17R,18S)-28-O-benzyl-3-aldehyde oleanolic acid being replaced with (3R,5S,8R,9R,10S,14R,17R,18S)-28-O-benzyl-3-aldehyde oleanolic acid. A56 (yield 68%) was obtained using the same procedure as in Example 2. 1H NMR (500 MHz, MeOD) δ 5.28 (s, 1H), 4.16 (s, 1H), 3.79 (d, J = 2.0 Hz, 2H), 3.46 (dd, J = 20.4, 9.3 Hz, 2H), 3.38 (s, 1H), 3.35 - 3.31 (m, 1H), 3.23 (d, J = 9.5 Hz, 1H), 3.11 (d, J = 9.5 Hz, 1H), 2.88 (dd, J = 13.5, 3.0 Hz, 1H), 2.03 (dd, J = 13.5, 10.3 Hz, 1H), 1.93 (d, J = 7.1Hz, 2H), 1.86 - 1.05 (m, 21H), 1.06 - 0.93 (m, 12H), 0.90 - 0.82 (m, 6H), 0.81 (d, J = 11.4 Hz, 1H). LRMS (ESI):633.42 [MH] - .

[0132] Example 57 (3S,5S,8R,9R,10S,14R,17R,18S)-oleanolic acid-3-methyl-6"-deoxy-6"-fluoro-β-D-glucopyranoside (A57) A57 (yield 65%) was obtained using the same raw materials, reagents and production method as in Example 6, except that 2,3,4,6-O-tetrabenzyl-1-(pyridin-1-yl)sulfonyl-β-D-thioglucopyranoside was replaced with 2,3,4,6-O-tetrabenzyl-1-(pyridin-1-yl)sulfonyl-6-deoxy-6-fluoro-β-D-thioglucopyranoside. 1H NMR (500 MHz, MeOD) δ 5.28 (s, 1H), 4.16 (s, 1H), 3.79 (d, J = 2.0 Hz, 2H), 3.46 (dd, J = 20.4, 9.3 Hz, 2H), 3.38 (s, 1H), 3.35 - 3.31 (m, 1H), 3.23 (d, J = 9.5 Hz, 1H), 3.11 (d, J = 9.5 Hz, 1H), 2.88 (dd, J = 13.5, 3.0 Hz, 1H), 2.03 (dd, J = 13.5, 10.3 Hz, 1H), 1.93 (d, J = 7.1Hz, 2H), 1.86 - 1.05 (m, 21H), 1.06 - 0.93 (m, 12H), 0.90 - 0.82 (m, 6H), 0.81 (d, J = 11.4 Hz, 1H). LRMS (ESI):617.43 [MH] - .

[0133] Example 58 3R,5S,8R,9R,10S,14R,17R,18S)-Oleanolic acid-3-methyl-6"-deoxy-6"-fluoro-β-D-glucopyranoside (A58) The remaining raw materials, reagents, and production method were the same as in Example 6, but A58 (yield 66%) was obtained. 1H NMR (500 MHz, MeOD) δ 5.28 (s, 1H), 4.16 (s, 1H), 3.79 (d, J = 2.0 Hz, 2H), 3.46 (dd, J = 20.4, 9.3 Hz, 2H), 3.38 (s, 1H), 3.35 - 3.31 (m, 1H), 3.23 (d, J = 9.5 Hz, 1H), 3.11 (d, J = 9.5 Hz, 1H), 2.88 (dd, J = 13.5, 3.0 Hz, 1H), 2.03 (dd, J = 13.5, 10.3 Hz, 1H), 1.93 (d, J = 7.1Hz, 2H), 1.86 - 1.05 (m, 21H), 1.06 - 0.93 (m, 12H), 0.90 - 0.82 (m, 6H), 0.81 (d, J = 11.4 Hz, 1H). LRMS (ESI):617.43 [MH] - .

[0134] Example 59 (3S,5S,8R,9R,10S,14R,17R,18S)-Oleanolic acid 3-carbonyl-6"-deoxy-6"-fluoro-β-D-glucopyranoside (A59) A59 (yield 86%) was obtained using the same raw materials, reagents, and production method as in Example 10, except that 2,3,4,6-O-tetrabenzyl-1-(pyridin-1-yl)sulfonyl-β-D-thioglucopyranoside was replaced with 2,3,4,6-O-tetrabenzyl-1-(pyridin-1-yl)sulfonyl-6-deoxy-6-fluoro-β-D-thioglucopyranoside. 1H NMR (500 MHz, MeOD) δ 5.28 (s, 1H), 4.16 (s, 1H), 3.79 (d, J = 2.0 Hz, 2H), 3.46 (dd, J = 20.4, 9.3 Hz, 2H), 3.38 (s, 1H), 3.35 - 3.31 (m, 1H), 3.23 (d, J = 9.5 Hz, 1H), 3.11 (d, J = 9.5 Hz, 1H), 2.88 (dd, J = 13.5, 3.0 Hz, 1H), 2.03 (dd, J = 13.5, 10.3 Hz, 1H), 1.93 (d, J = 7.1Hz, 2H), 1.86 - 1.05 (m, 21H), 1.06 - 0.93 (m, 12H), 0.90 - 0.82 (m, 6H), 0.81 (d, J = 11.4 Hz, 1H). LRMS (ESI):631.41 [MH] - .

[0135] Example 60 (3R,5S,8R,9R,10S,14R,17R,18S)-oleanolic acid-3-carbonyl-6"-deoxy-6"-fluoro-β-D-glucopyranoside (A60) The remaining raw materials, reagents, and production method were the same as in Example 10, but A60 (yield 89%) was obtained. 1H NMR (500 MHz, MeOD) δ 5.28 (s, 1H), 4.16 (s, 1H), 3.79 (d, J = 2.0 Hz, 2H), 3.46 (dd, J = 20.4, 9.3 Hz, 2H), 3.38 (s, 1H), 3.35 - 3.31 (m, 1H), 3.23 (d, J = 9.5 Hz, 1H), 3.11 (d, J = 9.5 Hz, 1H), 2.88 (dd, J = 13.5, 3.0 Hz, 1H), 2.03 (dd, J = 13.5, 10.3 Hz, 1H), 1.93 (d, J = 7.1Hz, 2H), 1.86 - 1.05 (m, 21H), 1.06 - 0.93 (m, 12H), 0.90 - 0.82 (m, 6H), 0.81 (d, J = 11.4 Hz, 1H). LRMS (ESI):631.41 [MH] - .

[0136] Example 61 (3S,5S,8R,9R,10S,14R,17R,18S)-oleanolic acid-3-(1'R)-(hydroxy)methyl-β-D-xylopyranose (1→3)-β-D-glucuronopyranoside (A61) The remaining raw materials, reagents, and production method were the same as in Example 2, except that 2,3,4,6-O-tetrabenzyl-1-(pyridin-1-yl)sulfonyl-β-D-thioglucopyranoside was replaced with 2,3,4,6-O-tetrabenzyl-1-(pyridin-1-yl)sulfonyl-β-D-xylopyranose(1→3)-β-D-thioglucuronopyranoside. A61 (yield 70%) was obtained using the same method as in Example 2. 1H NMR (500 MHz, MeOD) δ 5.28 (s, 1H), 4.16 (s, 1H), 3.79 (d, J = 2.0 Hz, 2H), 3.46 (dd, J = 20.4, 9.3 Hz, 2H), 3.38 (s, 1H), 3.35 - 3.31 (m, 1H), 3.23 (d, J = 9.5 Hz, 1H), 3.11 (d, J = 9.5 Hz, 1H), 2.88 (dd, J = 13.5, 3.0 Hz, 1H), 2.03 (dd, J = 13.5, 10.3 Hz, 1H), 1.93 (d, J = 7.1Hz, 2H), 1.86 - 1.05 (m, 21H), 1.06 - 0.93 (m, 12H), 0.90 - 0.82 (m, 6H), 0.81 (d, J = 11.4 Hz, 1H). LRMS (ESI):777.45[MH] - .

[0137] Example 62 (3R,5S,8R,9R,10S,14R,17R,18S)-oleanolic acid-3-(1'R)-(hydroxy)methyl-β-D-xylopyranose (1→3)-β-D-glucuronopyranoside (A62) The remaining raw materials, reagents, and preparation method were the same as in Example 2, but A62 (yield 68%) was obtained. 1H NMR (500 MHz, MeOD) δ 5.28 (s, 1H), 4.16 (s, 1H), 3.79 (d, J = 2.0 Hz, 2H), 3.46 (dd, J = 20.4, 9.3 Hz, 2H), 3.38 (s, 1H), 3.35 - 3.31 (m, 1H), 3.23 (d, J = 9.5 Hz, 1H), 3.11 (d, J = 9.5 Hz, 1H), 2.88 (dd, J = 13.5, 3.0 Hz, 1H), 2.03 (dd, J = 13.5, 10.3 Hz, 1H), 1.93 (d, J = 7.1Hz, 2H), 1.86 - 1.05 (m, 21H), 1.06 - 0.93 (m, 12H), 0.90 - 0.82 (m, 6H), 0.81 (d, J = 11.4 Hz, 1H). LRMS (ESI):777.45 [MH] - .

[0138] Example 63 (3S,5S,8R,9R,10S,14R,17R,18S)-oleanolic acid-3-methyl-β-D-xylopyranose (1→3)-β-D-glucuronopyranoside (A63) A63 (yield 69%) was obtained using the same raw materials, reagents, and production method as in Example 6, except that 2,3,4,6-O-tetrabenzyl-1-(pyridin-1-yl)sulfonyl-β-D-thioglucopyranoside was replaced with 2,3,4,6-O-tetrabenzyl-1-(pyridin-1-yl)sulfonyl-β-D-xylopyranose(1→3)-β-D-thioglucuronopyranoside. 1H NMR (500 MHz, MeOD) δ 5.28 (s, 1H), 4.16 (s, 1H), 3.79 (d, J = 2.0 Hz, 2H), 3.46 (dd, J = 20.4, 9.3 Hz, 2H), 3.38 (s, 1H), 3.35 - 3.31 (m, 1H), 3.23 (d, J = 9.5 Hz, 1H), 3.11 (d, J = 9.5 Hz, 1H), 2.88 (dd, J = 13.5, 3.0 Hz, 1H), 2.03 (dd, J = 13.5, 10.3 Hz, 1H), 1.93 (d, J = 7.1Hz, 2H), 1.86 - 1.05 (m, 21H), 1.06 - 0.93 (m, 12H), 0.90 - 0.82 (m, 6H), 0.81 (d, J = 11.4 Hz, 1H). LRMS (ESI):761.46 [MH].

[0139] Example 64 (3R,5S,8R,9R,10S,14R,17R,18S)-oleanolic acid-3-methyl-β-D-xylopyranose (1→3)-β-D-glucuronopyranoside (A64) The remaining raw materials, reagents, and preparation methods were the same as in Example 6, but with the exception of 2,3,4,6-O-tetrabenzyl-1-(pyridin-1-yl)sulfonyl-β-D-thioglucopyranoside being replaced with 2,3,4,6-O-tetrabenzyl-1-(pyridin-1-yl)sulfonyl-β-D-xylopyranose (1→3)-β-D-thioglucuronopyranoside, and (3S,5S,8R,9R,10S,14R,17R,18S)-28-O-benzyl-3-aldehyde oleanolic acid being replaced with (3R,5S,8R,9R,10S,14R,17R,18S)-28-O-benzyl-3-aldehyde oleanolic acid. A64 (70% yield) was obtained using the same procedures as in Example 6. 1H NMR (500 MHz, MeOD) δ 5.28 (s, 1H), 4.16 (s, 1H), 3.79 (d, J = 2.0 Hz, 2H), 3.46 (dd, J = 20.4, 9.3 Hz, 2H), 3.38 (s, 1H), 3.35 - 3.31 (m, 1H), 3.23 (d, J = 9.5 Hz, 1H), 3.11 (d, J = 9.5 Hz, 1H), 2.88 (dd, J = 13.5, 3.0 Hz, 1H), 2.03 (dd, J = 13.5, 10.3 Hz, 1H), 1.93 (d, J = 7.1Hz, 2H), 1.86 - 1.05 (m, 21H), 1.06 - 0.93 (m, 12H), 0.90 - 0.82 (m, 6H), 0.81 (d, J = 11.4 Hz, 1H). LRMS (ESI):761.46 [MH] - .

[0140] Example 65 (3S,5S,8R,9R,10S,14R,17R,18S)-oleanolic acid-3-carbonyl-β-D-xylopyranose (1→3)-β-D-glucuronopyranoside (A65) A65 (yield 86%) was obtained using the same raw materials, reagents, and production method as in Example 10, except that 2,3,4,6-O-tetrabenzyl-1-(pyridin-1-yl)sulfonyl-β-D-thioglucopyranoside was replaced with 2,3,4,6-O-tetrabenzyl-1-(pyridin-1-yl)sulfonyl-β-D-xylopyranose (1→3)-β-D-thioglucuronopyranoside. 1H NMR (500 MHz, MeOD) δ 5.28 (s, 1H), 4.16 (s, 1H), 3.79 (d, J = 2.0 Hz, 2H), 3.46 (dd, J = 20.4, 9.3 Hz, 2H), 3.38 (s, 1H), 3.35 - 3.31 (m, 1H), 3.23 (d, J = 9.5 Hz, 1H), 3.11 (d, J = 9.5 Hz, 1H), 2.88 (dd, J = 13.5, 3.0 Hz, 1H), 2.03 (dd, J = 13.5, 10.3 Hz, 1H), 1.93 (d, J = 7.1Hz, 2H), 1.86 - 1.05 (m, 21H), 1.06 - 0.93 (m, 12H), 0.90 - 0.82 (m, 6H), 0.81 (d, J = 11.4 Hz, 1H). LRMS (ESI):775.43 [MH] - .

[0141] Example 66 (3R,5S,8R,9R,10S,14R,17R,18S)-oleanolic acid-3-carbonyl-β-D-xylopyranose (1→3)-β-D-glucuronopyranoside (A66) The remaining raw materials, reagents, and preparation methods were the same as in Example 10, but A66 (yield 89%) was obtained. 1H NMR (500 MHz, MeOD) δ 5.28 (s, 1H), 4.16 (s, 1H), 3.79 (d, J = 2.0 Hz, 2H), 3.46 (dd, J = 20.4, 9.3 Hz, 2H), 3.38 (s, 1H), 3.35 - 3.31 (m, 1H), 3.23 (d, J = 9.5 Hz, 1H), 3.11 (d, J = 9.5 Hz, 1H), 2.88 (dd, J = 13.5, 3.0 Hz, 1H), 2.03 (dd, J = 13.5, 10.3 Hz, 1H), 1.93 (d, J = 7.1Hz, 2H), 1.86 - 1.05 (m, 21H), 1.06 - 0.93 (m, 12H), 0.90 - 0.82 (m, 6H), 0.81 (d, J = 11.4 Hz, 1H). LRMS (ESI):775.43 [MH] - .

[0142] Example 67 (3S,5S,8R,9R,10S,14R,17R,18S,19S,20R)-Ursolic acid-3-(1'R)-(hydroxy)methyl-β-D-glucuronopyranoside (A67) The remaining raw materials, reagents, and production method were the same as in Example 2, but the compound A67 (yield 72%) was obtained. 1H NMR (500 MHz, MeOD) δ 5.28 (s, 1H), 4.16 (s, 1H), 3.79 (d, J = 2.0 Hz, 2H), 3.46 (dd, J = 20.4, 9.3 Hz, 2H), 3.38 (s, 1H), 3.35 - 3.31 (m, 1H), 3.23 (d, J = 9.5 Hz, 1H), 3.11 (d, J = 9.5 Hz, 1H), 2.88 (dd, J = 13.5, 3.0 Hz, 1H), 2.03 (dd, J = 13.5, 10.3 Hz, 1H), 1.93 (d, J = 7.1Hz, 2H), 1.86 - 1.05 (m, 21H), 1.06 - 0.93 (m, 12H), 0.90 - 0.82 (m, 6H), 0.81 (d, J = 11.4 Hz, 1H). LRMS (ESI):645.41 [MH] - .

[0143] Example 68 (3R,5S,8R,9R,10S,14R,17R,18S,19S,20R)-Ursolic acid-3-(1'R)-(hydroxy)methyl-β-D-glucuronopyranoside (A68) The remaining raw materials, reagents, and production method were the same as in Example 2, but with the exception of 2,3,4,6-O-tetrabenzyl-1-(pyridin-1-yl)sulfonyl-β-D-thioglucopyranoside, which was replaced with 2,3,4,6-O-tetrabenzyl-1-(pyridin-1-yl)sulfonyl-β-D-thioglucuronopyranoside, and (3S,5S,8R,9R,10S,14R,17R,18S)-28-O-benzyl-3-aldehyde oleanolic acid, which was replaced with (3R,5S,8R,9R,10S,14R,17R,18S,19S,20R)-28-O-benzyl-3-aldehyde ursolic acid. A68 (yield 68%) was obtained using the same method as in Example 2. 1H NMR (500 MHz, MeOD) δ 5.28 (s, 1H), 4.16 (s, 1H), 3.79 (d, J = 2.0 Hz, 2H), 3.46 (dd, J = 20.4, 9.3 Hz, 2H), 3.38 (s, 1H), 3.35 - 3.31 (m, 1H), 3.23 (d, J = 9.5 Hz, 1H), 3.11 (d, J = 9.5 Hz, 1H), 2.88 (dd, J = 13.5, 3.0 Hz, 1H), 2.03 (dd, J = 13.5, 10.3 Hz, 1H), 1.93 (d, J = 7.1Hz, 2H), 1.86 - 1.05 (m, 21H), 1.06 - 0.93 (m, 12H), 0.90 - 0.82 (m, 6H), 0.81 (d, J = 11.4 Hz, 1H). LRMS (ESI):645.41 [MH] - .

[0144] Example 69 (3S,5S,8R,9R,10S,14R,17R,18S,19S,20R)-Ursolic acid-3-methyl-β-D-glucuronopyranoside (A69) The remaining raw materials, reagents, and production method were the same as in Example 6, but with the exception of 2,3,4,6-O-tetrabenzyl-1-(pyridin-1-yl)sulfonyl-β-D-thioglucopyranoside, which was replaced with 2,3,4,6-O-tetrabenzyl-1-(pyridin-1-yl)sulfonyl-β-D-thioglucuronopyranoside, and (3S,5S,8R,9R,10S,14R,17R,18S)-28-O-benzyl-3-aldehyde oleanolic acid, which was replaced with (3S,5S,8R,9R,10S,14R,17R,18S,19S,20R)-28-O-benzyl-3-aldehyde ursolic acid. A69 (yield 68%) was obtained using the same method as in Example 6. 1H NMR (500 MHz, MeOD) δ 5.28 (s, 1H), 4.16 (s, 1H), 3.79 (d, J = 2.0 Hz, 2H), 3.46 (dd, J = 20.4, 9.3 Hz, 2H), 3.38 (s, 1H), 3.35 - 3.31 (m, 1H), 3.23 (d, J = 9.5 Hz, 1H), 3.11 (d, J = 9.5 Hz, 1H), 2.88 (dd, J = 13.5, 3.0 Hz, 1H), 2.03 (dd, J = 13.5, 10.3 Hz, 1H), 1.93 (d, J = 7.1Hz, 2H), 1.86 - 1.05 (m, 21H), 1.06 - 0.93 (m, 12H), 0.90 - 0.82 (m, 6H), 0.81 (d, J = 11.4 Hz, 1H). LRMS (ESI):613.42 [MH] - .

[0145] Example 70 (3R,5S,8R,9R,10S,14R,17R,18S,19S,20R)-Ursolic acid 3-methyl-β-D-glucuronopyranoside (A70) The remaining raw materials, reagents, and preparation method were the same as in Example 6, but with the exception of 2,3,4,6-O-tetrabenzyl-1-(pyridin-1-yl)sulfonyl-β-D-thioglucopyranoside, which was replaced with 2,3,4,6-O-tetrabenzyl-1-(pyridin-1-yl)sulfonyl-β-D-thioglucuronopyranoside, and (3S,5S,8R,9R,10S,14R,17R,18S)-28-O-benzyl-3-aldehyde oleanolic acid, which was replaced with (3R,5S,8R,9R,10S,14R,17R,18S,19S,20R)-28-O-benzyl-3-aldehyde ursolic acid. A70 (yield 63%) was obtained using the same method as in Example 6. 1H NMR (500 MHz, MeOD) δ 5.28 (s, 1H), 4.16 (s, 1H), 3.79 (d, J = 2.0 Hz, 2H), 3.46 (dd, J = 20.4, 9.3 Hz, 2H), 3.38 (s, 1H), 3.35 - 3.31 (m, 1H), 3.23 (d, J = 9.5 Hz, 1H), 3.11 (d, J = 9.5 Hz, 1H), 2.88 (dd, J = 13.5, 3.0 Hz, 1H), 2.03 (dd, J = 13.5, 10.3 Hz, 1H), 1.93 (d, J = 7.1Hz, 2H), 1.86 - 1.05 (m, 21H), 1.06 - 0.93 (m, 12H), 0.90 - 0.82 (m, 6H), 0.81 (d, J = 11.4 Hz, 1H). LRMS (ESI):613.42 [MH] - .

[0146] Example 71 (3S,5S,8R,9R,10S,14R,17R,18S,19S,20R)-Ursolic acid-3-carbonyl-β-D-glucuronopyranoside (A71) The remaining raw materials, reagents, and preparation method were the same as in Example 10, but with the exception of 2,3,4,6-O-tetrabenzyl-1-(pyridin-1-yl)sulfonyl-β-D-thioglucopyranoside being replaced with 2,3,4,6-O-tetrabenzyl-1-(pyridin-1-yl)sulfonyl-β-D-thioglucuronopyranoside, and (3S,5S,8R,9R,10S,14R,17R,18S)-28-O-benzyl-3-aldehyde oleanolic acid being replaced with (3S,5S,8R,9R,10S,14R,17R,18S,19S,20R)-28-O-benzyl-3-aldehyde ursolic acid. A71 (yield 85%) was obtained using the same method as in Example 10. 1H NMR (500 MHz, MeOD) δ 5.28 (s, 1H), 4.16 (s, 1H), 3.79 (d, J = 2.0 Hz, 2H), 3.46 (dd, J = 20.4, 9.3 Hz, 2H), 3.38 (s, 1H), 3.35 - 3.31 (m, 1H), 3.23 (d, J = 9.5 Hz, 1H), 3.11 (d, J = 9.5 Hz, 1H), 2.88 (dd, J = 13.5, 3.0 Hz, 1H), 2.03 (dd, J = 13.5, 10.3 Hz, 1H), 1.93 (d, J = 7.1Hz, 2H), 1.86 - 1.05 (m, 21H), 1.06 - 0.93 (m, 12H), 0.90 - 0.82 (m, 6H), 0.81 (d, J = 11.4 Hz, 1H). LRMS (ESI):627.40 [MH] - .

[0147] Example 72 (3R,5S,8R,9R,10S,14R,17R,18S,19S,20R)-Ursolic acid-3-carbonyl-β-D-glucuronopyranoside (A72) The remaining raw materials, reagents, and preparation method were the same as in Example 10, but A72 (yield 89%) was obtained. 1H NMR (500 MHz, MeOD) δ 5.28 (s, 1H), 4.16 (s, 1H), 3.79 (d, J = 2.0 Hz, 2H), 3.46 (dd, J = 20.4, 9.3 Hz, 2H), 3.38 (s, 1H), 3.35 - 3.31 (m, 1H), 3.23 (d, J = 9.5 Hz, 1H), 3.11 (d, J = 9.5 Hz, 1H), 2.88 (dd, J = 13.5, 3.0 Hz, 1H), 2.03 (dd, J = 13.5, 10.3 Hz, 1H), 1.93 (d, J = 7.1Hz, 2H), 1.86 - 1.05 (m, 21H), 1.06 - 0.93 (m, 12H), 0.90 - 0.82 (m, 6H), 0.81 (d, J = 11.4 Hz, 1H). LRMS (ESI):627.40 [MH] - .

[0148] Example 73 (3S,5S,8R,9R,10S,13R,14R,17S,18R,19R)-Betulinic acid-3-(1'R)-(hydroxy)methyl-β-D-glucuronopyranoside (A73) The remaining raw materials, reagents, and preparation method were the same as in Example 2, but with the exception of 2,3,4,6-O-tetrabenzyl-1-(pyridin-1-yl)sulfonyl-β-D-thioglucuronopyranoside, and (3S,5S,8R,9R,10S,14R,17R,18S)-28-O-benzyl-3-aldehyde oleanolic acid, the compound A73 (yield 71%) was obtained. 1H NMR (500 MHz, MeOD) δ 5.28 (s, 1H), 4.16 (s, 1H), 3.79 (d, J = 2.0 Hz, 2H), 3.46 (dd, J = 20.4, 9.3 Hz, 2H), 3.38 (s, 1H), 3.35 - 3.31 (m, 1H), 3.23 (d, J = 9.5 Hz, 1H), 3.11 (d, J = 9.5 Hz, 1H), 2.88 (dd, J = 13.5, 3.0 Hz, 1H), 2.03 (dd, J = 13.5, 10.3 Hz, 1H), 1.93 (d, J = 7.1Hz, 2H), 1.86 - 1.05 (m, 21H), 1.06 - 0.93 (m, 12H), 0.90 - 0.82 (m, 6H), 0.81 (d, J = 11.4 Hz, 1H). LRMS (ESI):645.41 [MH] - .

[0149] Example 74 (3S,5S,8R,9R,10S,13R,14R,17S,18R,19R)-Betulinic acid-3-(1'R)-(hydroxy)methyl-β-D-glucuronopyranoside (A74) The remaining raw materials, reagents, and preparation method were the same as in Example 2, but with the exception of 2,3,4,6-O-tetrabenzyl-1-(pyridin-1-yl)sulfonyl-β-D-thioglucuronopyranoside, and (3S,5S,8R,9R,10S,14R,17R,18S)-28-O-benzyl-3-aldehyde oleanolic acid, the compound A74 (yield 69%) was obtained. 1H NMR (500 MHz, MeOD) δ 5.28 (s, 1H), 4.16 (s, 1H), 3.79 (d, J = 2.0 Hz, 2H), 3.46 (dd, J = 20.4, 9.3 Hz, 2H), 3.38 (s, 1H), 3.35 - 3.31 (m, 1H), 3.23 (d, J = 9.5 Hz, 1H), 3.11 (d, J = 9.5 Hz, 1H), 2.88 (dd, J = 13.5, 3.0 Hz, 1H), 2.03 (dd, J = 13.5, 10.3 Hz, 1H), 1.93 (d, J = 7.1Hz, 2H), 1.86 - 1.05 (m, 21H), 1.06 - 0.93 (m, 12H), 0.90 - 0.82 (m, 6H), 0.81 (d, J = 11.4 Hz, 1H). LRMS (ESI):645.41 [MH] - .

[0150] Example 75 (3S,5S,8R,9R,10S,13R,14R,17S,18R,19R)-Betulinic acid-3-methyl-β-D-glucuronopyranoside (A75) The remaining raw materials, reagents, and preparation method were the same as in Example 6, except that 2,3,4,6-O-tetrabenzyl-1-(pyridin-1-yl)sulfonyl-β-D-thioglucopyranoside was replaced with 2,3,4,6-O-tetrabenzyl-1-(pyridin-1-yl)sulfonyl-β-D-thioglucuronopyranoside, and (3S,5S,8R,9R,10S,14R,17R,18S)-28-O-benzyl-3-aldehyde oleanolic acid was replaced with (3S,5S,8R,9R,10S,13R,14R,17S,18R,19R)-28-O-benzyl-3-aldehyde betulinic acid. A75 (yield 70%) was obtained using the same method as in Example 6. 1H NMR (500 MHz, MeOD) δ 5.28 (s, 1H), 4.16 (s, 1H), 3.79 (d, J = 2.0 Hz, 2H), 3.46 (dd, J = 20.4, 9.3 Hz, 2H), 3.38 (s, 1H), 3.35 - 3.31 (m, 1H), 3.23 (d, J = 9.5 Hz, 1H), 3.11 (d, J = 9.5 Hz, 1H), 2.88 (dd, J = 13.5, 3.0 Hz, 1H), 2.03 (dd, J = 13.5, 10.3 Hz, 1H), 1.93 (d, J = 7.1Hz, 2H), 1.86 - 1.05 (m, 21H), 1.06 - 0.93 (m, 12H), 0.90 - 0.82 (m, 6H), 0.81 (d, J = 11.4 Hz, 1H). LRMS (ESI):613.42 [MH] - .

[0151] Example 76 (3S,5S,8R,9R,10S,13R,14R,17S,18R,19R)-Betulinic acid-3-methyl-β-D-glucuronopyranoside (A76) The remaining raw materials, reagents, and preparation method were the same as in Example 6, but with the exception of 2,3,4,6-O-tetrabenzyl-1-(pyridin-1-yl)sulfonyl-β-D-thioglucuronopyranoside, and (3S,5S,8R,9R,10S,14R,17R,18S)-28-O-benzyl-3-aldehyde oleanolic acid, the other compounds were replaced with (3R,5S,8R,9R,10S,13R,14R,17S,18R,19R)-28-O-benzyl-3-aldehyde betulinic acid. A76 (yield 65%) was obtained using the same method as in Example 6. 1H NMR (500 MHz, MeOD) δ 5.28 (s, 1H), 4.16 (s, 1H), 3.79 (d, J = 2.0 Hz, 2H), 3.46 (dd, J = 20.4, 9.3 Hz, 2H), 3.38 (s, 1H), 3.35 - 3.31 (m, 1H), 3.23 (d, J = 9.5 Hz, 1H), 3.11 (d, J = 9.5 Hz, 1H), 2.88 (dd, J = 13.5, 3.0 Hz, 1H), 2.03 (dd, J = 13.5, 10.3 Hz, 1H), 1.93 (d, J = 7.1Hz, 2H), 1.86 - 1.05 (m, 21H), 1.06 - 0.93 (m, 12H), 0.90 - 0.82 (m, 6H), 0.81 (d, J = 11.4 Hz, 1H). LRMS (ESI):613.42 [MH] - .

[0152] Example 77 (3S,5S,8R,9R,10S,13R,14R,17S,18R,19R)-Betulinic acid-3-carbonyl-β-D-glucuronopyranoside (A77) The remaining raw materials, reagents, and preparation method were the same as in Example 10, except that 2,3,4,6-O-tetrabenzyl-1-(pyridin-1-yl)sulfonyl-β-D-thioglucopyranoside was replaced with 2,3,4,6-O-tetrabenzyl-1-(pyridin-1-yl)sulfonyl-β-D-thioglucuronopyranoside, and (3S,5S,8R,9R,10S,14R,17R,18S)-28-O-benzyl-3-aldehyde oleanolic acid was replaced with (3S,5S,8R,9R,10S,13R,14R,17S,18R,19R)-28-O-benzyl-3-aldehyde betulinic acid. A77 (yield 88%) was obtained using the same method as in Example 10. 1H NMR (500 MHz, MeOD) δ 5.28 (s, 1H), 4.16 (s, 1H), 3.79 (d, J = 2.0 Hz, 2H), 3.46 (dd, J = 20.4, 9.3 Hz, 2H), 3.38 (s, 1H), 3.35 - 3.31 (m, 1H), 3.23 (d, J = 9.5 Hz, 1H), 3.11 (d, J = 9.5 Hz, 1H), 2.88 (dd, J = 13.5, 3.0 Hz, 1H), 2.03 (dd, J = 13.5, 10.3 Hz, 1H), 1.93 (d, J = 7.1Hz, 2H), 1.86 - 1.05 (m, 21H), 1.06 - 0.93 (m, 12H), 0.90 - 0.82 (m, 6H), 0.81 (d, J = 11.4 Hz, 1H). LRMS (ESI):627.40 [MH] - .

[0153] Example 78 (3S,5S,8R,9R,10S,13R,14R,17S,18R,19R)-Betulinic acid-3-carbonyl-β-D-glucuronopyranoside (A78) The remaining raw materials, reagents, and preparation method were the same as in Example 10, but with the exception of 2,3,4,6-O-tetrabenzyl-1-(pyridin-1-yl)sulfonyl-β-D-thioglucuronopyranoside, and (3S,5S,8R,9R,10S,14R,17R,18S)-28-O-benzyl-3-aldehyde oleanolic acid, the other compounds were replaced with (3R,5S,8R,9R,10S,13R,14R,17S,18R,19R)-28-O-benzyl-3-aldehyde betulinic acid. A78 (89% yield) was obtained using the same method as in Example 10. 1H NMR (500 MHz, MeOD) δ 5.28 (s, 1H), 4.16 (s, 1H), 3.79 (d, J = 2.0 Hz, 2H), 3.46 (dd, J = 20.4, 9.3 Hz, 2H), 3.38 (s, 1H), 3.35 - 3.31 (m, 1H), 3.23 (d, J = 9.5 Hz, 1H), 3.11 (d, J = 9.5 Hz, 1H), 2.88 (dd, J = 13.5, 3.0 Hz, 1H), 2.03 (dd, J = 13.5, 10.3 Hz, 1H), 1.93 (d, J = 7.1Hz, 2H), 1.86 - 1.05 (m, 21H), 1.06 - 0.93 (m, 12H), 0.90 - 0.82 (m, 6H), 0.81 (d, J = 11.4 Hz, 1H). LRMS (ESI):627.40 [MH] - .

[0154] Example 79 (5S,8R,9R,10S,14R,17R,18S)-3-carbonyloleanolic acid-28-β-D-glucuronopyranoside (A79) The remaining raw materials, reagents, and production method were the same as in Example 2, but with the exception of 2,3,4,6-O-tetrabenzyl-1-(pyridin-1-yl)sulfonyl-β-D-thioglucopyranoside being replaced with 2,3,4,6-O-tetrabenzyl-1-(pyridin-1-yl)sulfonyl-β-D-thioglucuronopyranoside, and (3S,5S,8R,9R,10S,14R,17R,18S)-28-O-benzyl-3-aldehyde oleanolic acid being replaced with (5S,8R,9R,10S,14R,17R,18S)-3-carbonyl-17-aldehyde oleanolic acid. A79 (yield 71%) was obtained using the same method as in Example 2. 1H NMR (500 MHz, MeOD) δ 5.28 (s, 1H), 4.16 (s, 1H), 3.79 (d, J = 2.0 Hz, 2H), 3.46 (dd, J = 20.4, 9.3 Hz, 2H), 3.38 (s, 1H), 3.35 - 3.31 (m, 1H), 3.23 (d, J = 9.5 Hz, 1H), 3.11 (d, J = 9.5 Hz, 1H), 2.88 (dd, J = 13.5, 3.0 Hz, 1H), 2.03 (dd, J = 13.5, 10.3 Hz, 1H), 1.93 (d, J = 7.1Hz, 2H), 1.86 - 1.05 (m, 21H), 1.06 - 0.93 (m, 12H), 0.90 - 0.82 (m, 6H), 0.81 (d, J = 11.4 Hz, 1H). LRMS (ESI):613.38 [MH] - .

[0155] Example 80 (5S,8R,9R,10S,14R,17R,18S)-3-carbonyloleanolic acid-17-(1'R)-(hydroxy)methyl-β-D-glucuronopyranoside (A80) The remaining raw materials, reagents, and production method were the same as in Example 6, but with the exception of 2,3,4,6-O-tetrabenzyl-1-(pyridin-1-yl)sulfonyl-β-D-thioglucopyranoside being replaced with 2,3,4,6-O-tetrabenzyl-1-(pyridin-1-yl)sulfonyl-β-D-thioglucuronopyranoside, and (3S,5S,8R,9R,10S,14R,17R,18S)-28-O-benzyl-3-aldehyde oleanolic acid being replaced with (5S,8R,9R,10S,14R,17R,18S)-3-carbonyl-17-aldehyde oleanolic acid. A80 (yield 69%) was obtained using the same method as in Example 6. 1H NMR (500 MHz, MeOD) δ 5.28 (s, 1H), 4.16 (s, 1H), 3.79 (d, J = 2.0 Hz, 2H), 3.46 (dd, J = 20.4, 9.3 Hz, 2H), 3.38 (s, 1H), 3.35 - 3.31 (m, 1H), 3.23 (d, J = 9.5 Hz, 1H), 3.11 (d, J = 9.5 Hz, 1H), 2.88 (dd, J = 13.5, 3.0 Hz, 1H), 2.03 (dd, J = 13.5, 10.3 Hz, 1H), 1.93 (d, J = 7.1Hz, 2H), 1.86 - 1.05 (m, 21H), 1.06 - 0.93 (m, 12H), 0.90 - 0.82 (m, 6H), 0.81 (d, J = 11.4 Hz, 1H). LRMS (ESI):615.40 [MH] - .

[0156] Example 81 (5S,8R,9R,10S,14R,17R,18S)-3-carbonyloleanolic acid-17-methyl-β-D-glucuronopyranoside (A81) The remaining raw materials, reagents, and production method were the same as in Example 10, but with the exception of 2,3,4,6-O-tetrabenzyl-1-(pyridin-1-yl)sulfonyl-β-D-thioglucopyranoside being replaced with 2,3,4,6-O-tetrabenzyl-1-(pyridin-1-yl)sulfonyl-β-D-thioglucuronopyranoside, and (3S,5S,8R,9R,10S,14R,17R,18S)-28-O-benzyl-3-aldehyde oleanolic acid being replaced with (5S,8R,9R,10S,14R,17R,18S)-3-carbonyl-17-aldehyde oleanolic acid. A81 (yield 90%) was obtained using the same method as in Example 10. 1H NMR (500 MHz, MeOD) δ 5.28 (s, 1H), 4.16 (s, 1H), 3.79 (d, J = 2.0 Hz, 2H), 3.46 (dd, J = 20.4, 9.3 Hz, 2H), 3.38 (s, 1H), 3.35 - 3.31 (m, 1H), 3.23 (d, J = 9.5 Hz, 1H), 3.11 (d, J = 9.5 Hz, 1H), 2.88 (dd, J = 13.5, 3.0 Hz, 1H), 2.03 (dd, J = 13.5, 10.3 Hz, 1H), 1.93 (d, J = 7.1Hz, 2H), 1.86 - 1.05 (m, 21H), 1.06 - 0.93 (m, 12H), 0.90 - 0.82 (m, 6H), 0.81 (d, J = 11.4 Hz, 1H). LRMS (ESI):599.40 [MH] - .

[0157] Example 82 (5S,8R,9R,10S,14R,17R,18S19S,20R)-3-carbonylursolic acid-28-β-D-glucuronopyranoside (A82) The remaining raw materials, reagents, and production method were the same as in Example 2, but with the exception of 2,3,4,6-O-tetrabenzyl-1-(pyridin-1-yl)sulfonyl-β-D-thioglucopyranoside, which was replaced with 2,3,4,6-O-tetrabenzyl-1-(pyridin-1-yl)sulfonyl-β-D-thioglucuronopyranoside, and (3S,5S,8R,9R,10S,14R,17R,18S)-28-O-benzyl-3-aldehyde oleanolic acid, which was replaced with (5S,8R,9R,10S,14R,17R,18S19S,20R)-3-carbonyl-17-aldehyde ursolic acid. A82 (72% yield) was obtained using the same method as in Example 2. 1H NMR (500 MHz, MeOD) δ 5.28 (s, 1H), 4.16 (s, 1H), 3.79 (d, J = 2.0 Hz, 2H), 3.46 (dd, J = 20.4, 9.3 Hz, 2H), 3.38 (s, 1H), 3.35 - 3.31 (m, 1H), 3.23 (d, J = 9.5 Hz, 1H), 3.11 (d, J = 9.5 Hz, 1H), 2.88 (dd, J = 13.5, 3.0 Hz, 1H), 2.03 (dd, J = 13.5, 10.3 Hz, 1H), 1.93 (d, J = 7.1Hz, 2H), 1.86 - 1.05 (m, 21H), 1.06 - 0.93 (m, 12H), 0.90 - 0.82 (m, 6H), 0.81 (d, J = 11.4 Hz, 1H). LRMS (ESI):613.38 [MH] - .

[0158] Example 83 (5S,8R,9R,10S,14R,17R,18S19S,20R)-3-carbonylursolic acid-17-(1'R)-(hydroxy)methyl-β-D-glucuronopyranoside (A83) The remaining raw materials, reagents, and production method were the same as in Example 6, but with the exception of 2,3,4,6-O-tetrabenzyl-1-(pyridin-1-yl)sulfonyl-β-D-thioglucopyranoside, which was replaced with 2,3,4,6-O-tetrabenzyl-1-(pyridin-1-yl)sulfonyl-β-D-thioglucuronopyranoside, and (3S,5S,8R,9R,10S,14R,17R,18S)-28-O-benzyl-3-aldehyde oleanolic acid, which was replaced with (5S,8R,9R,10S,14R,17R,18S19S,20R)-3-carbonyl-17-aldehyde ursolic acid. A83 (yield 69%) was obtained using the same method as in Example 6. 1H NMR (500 MHz, MeOD) δ 5.28 (s, 1H), 4.16 (s, 1H), 3.79 (d, J = 2.0 Hz, 2H), 3.46 (dd, J = 20.4, 9.3 Hz, 2H), 3.38 (s, 1H), 3.35 - 3.31 (m, 1H), 3.23 (d, J = 9.5 Hz, 1H), 3.11 (d, J = 9.5 Hz, 1H), 2.88 (dd, J = 13.5, 3.0 Hz, 1H), 2.03 (dd, J = 13.5, 10.3 Hz, 1H), 1.93 (d, J = 7.1Hz, 2H), 1.86 - 1.05 (m, 21H), 1.06 - 0.93 (m, 12H), 0.90 - 0.82 (m, 6H), 0.81 (d, J = 11.4 Hz, 1H). LRMS (ESI):615.40 [MH] - .

[0159] Example 84 (5S,8R,9R,10S,14R,17R,18S,19S,20R)-3-carbonylursolic acid-17-methyl-β-D-glucuronopyranoside (A84) The remaining raw materials, reagents, and production method were the same as in Example 10, but with the exception of 2,3,4,6-O-tetrabenzyl-1-(pyridin-1-yl)sulfonyl-β-D-thioglucopyranoside, which was replaced with 2,3,4,6-O-tetrabenzyl-1-(pyridin-1-yl)sulfonyl-β-D-thioglucuronopyranoside, and (3S,5S,8R,9R,10S,14R,17R,18S)-28-O-benzyl-3-aldehyde oleanolic acid, which was replaced with (5S,8R,9R,10S,14R,17R,18S19S,20R)-3-carbonyl-17-aldehyde ursolic acid. A84 (yield 86%) was obtained using the same method as in Example 10. 1H NMR (500 MHz, MeOD) δ 5.28 (s, 1H), 4.16 (s, 1H), 3.79 (d, J = 2.0 Hz, 2H), 3.46 (dd, J = 20.4, 9.3 Hz, 2H), 3.38 (s, 1H), 3.35 - 3.31 (m, 1H), 3.23 (d, J = 9.5 Hz, 1H), 3.11 (d, J = 9.5 Hz, 1H), 2.88 (dd, J = 13.5, 3.0 Hz, 1H), 2.03 (dd, J = 13.5, 10.3 Hz, 1H), 1.93 (d, J = 7.1Hz, 2H), 1.86 - 1.05 (m, 21H), 1.06 - 0.93 (m, 12H), 0.90 - 0.82 (m, 6H), 0.81 (d, J = 11.4 Hz, 1H). LRMS (ESI):599.40 [MH] - .

[0160] Example 85 (5S,8R,9R,10S,13R,14R,17S,18R,19R)-3-carbonylbetulinic acid-28-β-D-glucuronopyranoside (A85) The remaining raw materials, reagents, and preparation method were the same as in Example 2, except that 2,3,4,6-O-tetrabenzyl-1-(pyridin-1-yl)sulfonyl-β-D-thioglucopyranoside was replaced with 2,3,4,6-O-tetrabenzyl-1-(pyridin-1-yl)sulfonyl-β-D-thioglucuronopyranoside, and (3S,5S,8R,9R,10S,14R,17R,18S)-28-O-benzyl-3-aldehyde oleanolic acid was replaced with (5S,8R,9R,10S,13R,14R,17S,18R,19R)-3-carbonyl-17-aldehyde betulinic acid. A85 (yield 74%) was obtained using the same method as in Example 2. 1H NMR (500 MHz, MeOD) δ 5.28 (s, 1H), 4.16 (s, 1H), 3.79 (d, J = 2.0 Hz, 2H), 3.46 (dd, J = 20.4, 9.3 Hz, 2H), 3.38 (s, 1H), 3.35 - 3.31 (m, 1H), 3.23 (d, J = 9.5 Hz, 1H), 3.11 (d, J = 9.5 Hz, 1H), 2.88 (dd, J = 13.5, 3.0 Hz, 1H), 2.03 (dd, J = 13.5, 10.3 Hz, 1H), 1.93 (d, J = 7.1Hz, 2H), 1.86 - 1.05 (m, 21H), 1.06 - 0.93 (m, 12H), 0.90 - 0.82 (m, 6H), 0.81 (d, J = 11.4 Hz, 1H). LRMS (ESI):613.38 [MH] - .

[0161] Example 86 (5S,8R,9R,10S,13R,14R,17S,18R,19R)-3-carbonylbetulinic acid-17-(1'R)-(hydroxy)methyl-β-D-glucuronopyranoside (A86) The remaining raw materials, reagents, and preparation method were the same as in Example 6, but with the exception of 2,3,4,6-O-tetrabenzyl-1-(pyridin-1-yl)sulfonyl-β-D-thioglucuronopyranoside, and (3S,5S,8R,9R,10S,14R,17R,18S)-28-O-benzyl-3-aldehyde oleanolic acid, the compound A86 (yield 71%) was obtained. 1H NMR (500 MHz, MeOD) δ 5.28 (s, 1H), 4.16 (s, 1H), 3.79 (d, J = 2.0 Hz, 2H), 3.46 (dd, J = 20.4, 9.3 Hz, 2H), 3.38 (s, 1H), 3.35 - 3.31 (m, 1H), 3.23 (d, J = 9.5 Hz, 1H), 3.11 (d, J = 9.5 Hz, 1H), 2.88 (dd, J = 13.5, 3.0 Hz, 1H), 2.03 (dd, J = 13.5, 10.3 Hz, 1H), 1.93 (d, J = 7.1Hz, 2H), 1.86 - 1.05 (m, 21H), 1.06 - 0.93 (m, 12H), 0.90 - 0.82 (m, 6H), 0.81 (d, J = 11.4 Hz, 1H). LRMS (ESI):615.40 [MH] - .

[0162] Example 87 (5S,8R,9R,10S,13R,14R,17S,18R,19R)-3-carbonylbetulinic acid-17-methyl-β-D-glucuronopyranoside (A87) The remaining raw materials, reagents, and preparation method were the same as in Example 10, except that 2,3,4,6-O-tetrabenzyl-1-(pyridin-1-yl)sulfonyl-β-D-thioglucopyranoside was replaced with 2,3,4,6-O-tetrabenzyl-1-(pyridin-1-yl)sulfonyl-β-D-thioglucuronopyranoside, and (3S,5S,8R,9R,10S,14R,17R,18S)-28-O-benzyl-3-aldehyde oleanolic acid was replaced with (5S,8R,9R,10S,13R,14R,17S,18R,19R)-3-carbonyl-17-aldehyde betulinic acid. A87 (yield 85%) was obtained using the same method as in Example 10. 1H NMR (500 MHz, MeOD) δ 5.28 (s, 1H), 4.16 (s, 1H), 3.79 (d, J = 2.0 Hz, 2H), 3.46 (dd, J = 20.4, 9.3 Hz, 2H), 3.38 (s, 1H), 3.35 - 3.31 (m, 1H), 3.23 (d, J = 9.5 Hz, 1H), 3.11 (d, J = 9.5 Hz, 1H), 2.88 (dd, J = 13.5, 3.0 Hz, 1H), 2.03 (dd, J = 13.5, 10.3 Hz, 1H), 1.93 (d, J = 7.1Hz, 2H), 1.86 - 1.05 (m, 21H), 1.06 - 0.93 (m, 12H), 0.90 - 0.82 (m, 6H), 0.81 (d, J = 11.4 Hz, 1H). LRMS (ESI):599.40 [MH] - .

[0163] Example 88 (3S,5S,8R,9R,10S,14R,17R,18S)-28-O-Ethyloleanolic acid-3-(1'R)-(hydroxy)methyl-β-D-glucuronopyranoside (A88) The remaining raw materials, reagents, and production method were the same as in Example 2, but with the exception of 2,3,4,6-O-tetrabenzyl-1-(pyridin-1-yl)sulfonyl-β-D-thioglucopyranoside being replaced with 2,3,4,6-O-tetrabenzyl-1-(pyridin-1-yl)sulfonyl-β-D-thioglucuronopyranoside, and (3S,5S,8R,9R,10S,14R,17R,18S)-28-O-benzyl-3-aldehyde oleanolic acid being replaced with (3S,5S,8R,9R,10S,14R,17R,18S)-28-O-ethyl-3-aldehyde oleanolic acid. A88 (71% yield) was obtained using the same method as in Example 2, using the same raw materials, reagents, and production method as in Example 2. 1H NMR (500 MHz, MeOD) δ 5.28 (s, 1H), 4.16 (s, 1H), 3.79 (d, J = 2.0 Hz, 2H), 3.46 (dd, J = 20.4, 9.3 Hz, 2H), 3.38 (s, 1H), 3.35 - 3.31 (m, 1H), 3.23 (d, J = 9.5 Hz, 1H), 3.11 (d, J = 9.5 Hz, 1H), 2.88 (dd, J = 13.5, 3.0 Hz, 1H), 2.03 (dd, J = 13.5, 10.3 Hz, 1H), 1.93 (d, J = 7.1Hz, 2H), 1.86 - 1.05 (m, 21H), 1.06 - 0.93 (m, 12H), 0.90 - 0.82 (m, 6H), 0.81 (d, J = 11.4 Hz, 1H). LRMS (ESI):673.44 [MH] - .

[0164] Example 89 (3S,5S,8R,9R,10S,14R,17R,18S)-28-O-allyl oleanolic acid-3-(1'R)-(hydroxy)methyl-β-D-glucuronopyranoside (A89) The remaining raw materials, reagents, and production method were the same as in Example 2, but with the exception of 2,3,4,6-O-tetrabenzyl-1-(pyridin-1-yl)sulfonyl-β-D-thioglucopyranoside being replaced with 2,3,4,6-O-tetrabenzyl-1-(pyridin-1-yl)sulfonyl-β-D-thioglucuronopyranoside, and (3S,5S,8R,9R,10S,14R,17R,18S)-28-O-benzyl-3-aldehyde oleanolic acid being replaced with (3S,5S,8R,9R,10S,14R,17R,18S)-28-O-allyl-3-aldehyde oleanolic acid. A89 (70% yield) was obtained using the same method as in Example 2. 1H NMR (500 MHz, MeOD) δ 5.28 (s, 1H), 4.16 (s, 1H), 3.79 (d, J = 2.0 Hz, 2H), 3.46 (dd, J = 20.4, 9.3 Hz, 2H), 3.38 (s, 1H), 3.35 - 3.31 (m, 1H), 3.23 (d, J = 9.5 Hz, 1H), 3.11 (d, J = 9.5 Hz, 1H), 2.88 (dd, J = 13.5, 3.0 Hz, 1H), 2.03 (dd, J = 13.5, 10.3 Hz, 1H), 1.93 (d, J = 7.1Hz, 2H), 1.86 - 1.05 (m, 21H), 1.06 - 0.93 (m, 12H), 0.90 - 0.82 (m, 6H), 0.81 (d, J = 11.4 Hz, 1H). LRMS (ESI):685.44 [MH] - .

[0165] Example 90 (3S,5S,8R,9R,10S,14R,17R,18S)-28-O-(O-ethyl)carboxymethyl oleanolic acid-3-(1'R)-(hydroxy)methyl-β-D-glucuronopyranoside (A90) The remaining raw materials, reagents, and production method were the same as in Example 2, but with the exception of 2,3,4,6-O-tetrabenzyl-1-(pyridin-1-yl)sulfonyl-β-D-thioglucopyranoside being replaced with 2,3,4,6-O-tetrabenzyl-1-(pyridin-1-yl)sulfonyl-β-D-thioglucuronopyranoside, and (3S,5S,8R,9R,10S,14R,17R,18S)-28-O-benzyl-3-aldehyde oleanolic acid being replaced with (3S,5S,8R,9R,10S,14R,17R,18S)-28-O-(O-ethyl)carboxymethyl-3-aldehyde oleanolic acid. A90 (yield 71%) was obtained using the same method as in Example 2. 1H NMR (500 MHz, MeOD) δ 5.28 (s, 1H), 4.16 (s, 1H), 3.79 (d, J = 2.0 Hz, 2H), 3.46 (dd, J = 20.4, 9.3 Hz, 2H), 3.38 (s, 1H), 3.35 - 3.31 (m, 1H), 3.23 (d, J = 9.5 Hz, 1H), 3.11 (d, J = 9.5 Hz, 1H), 2.88 (dd, J = 13.5, 3.0 Hz, 1H), 2.03 (dd, J = 13.5, 10.3 Hz, 1H), 1.93 (d, J = 7.1Hz, 2H), 1.86 - 1.05 (m, 21H), 1.06 - 0.93 (m, 12H), 0.90 - 0.82 (m, 6H), 0.81 (d, J = 11.4 Hz, 1H). LRMS (ESI):731.44 [MH] - .

[0166] Example 91 (3S,5S,8R,9R,10S,14R,17R,18S)-28-O-acetoxyoleanolic acid-3-(1'R)-(hydroxy)methyl-β-D-glucuronopyranoside (A91) The remaining raw materials, reagents, and production method were the same as in Example 2, but with the exception of 2,3,4,6-O-tetrabenzyl-1-(pyridin-1-yl)sulfonyl-β-D-thioglucopyranoside being replaced with 2,3,4,6-O-tetrabenzyl-1-(pyridin-1-yl)sulfonyl-β-D-thioglucuronopyranoside, and (3S,5S,8R,9R,10S,14R,17R,18S)-28-O-benzyl-3-aldehyde oleanolic acid being replaced with (3S,5S,8R,9R,10S,14R,17R,18S)-28-O-acetoxy-3-aldehyde oleanolic acid. A91 (yield 69%) was obtained using the same method as in Example 2. 1H NMR (500 MHz, MeOD) δ 5.28 (s, 1H), 4.16 (s, 1H), 3.79 (d, J = 2.0 Hz, 2H), 3.46 (dd, J = 20.4, 9.3 Hz, 2H), 3.38 (s, 1H), 3.35 - 3.31 (m, 1H), 3.23 (d, J = 9.5 Hz, 1H), 3.11 (d, J = 9.5 Hz, 1H), 2.88 (dd, J = 13.5, 3.0 Hz, 1H), 2.03 (dd, J = 13.5, 10.3 Hz, 1H), 1.93 (d, J = 7.1Hz, 2H), 1.86 - 1.05 (m, 21H), 1.06 - 0.93 (m, 12H), 0.90 - 0.82 (m, 6H), 0.81 (d, J = 11.4 Hz, 1H). LRMS (ESI):703.41 [MH] - .

[0167] Example 92 (3S,5S,8R,9R,10S,14R,17R,18S)-28-O-hydroxyethyl oleanolic acid-3-(1'R)-(hydroxy)methyl-β-D-glucuronopyranoside (A92) The remaining raw materials, reagents, and production method were the same as in Example 2, but with the exception of 2,3,4,6-O-tetrabenzyl-1-(pyridin-1-yl)sulfonyl-β-D-thioglucopyranoside being replaced with 2,3,4,6-O-tetrabenzyl-1-(pyridin-1-yl)sulfonyl-β-D-thioglucuronopyranoside, and (3S,5S,8R,9R,10S,14R,17R,18S)-28-O-benzyl-3-aldehyde oleanolic acid being replaced with (3S,5S,8R,9R,10S,14R,17R,18S)-28-O-hydroxyethyl-3-aldehyde oleanolic acid. A92 (71% yield) was obtained using the same method as in Example 2. 1H NMR (500 MHz, MeOD) δ 5.28 (s, 1H), 4.16 (s, 1H), 3.79 (d, J = 2.0 Hz, 2H), 3.46 (dd, J = 20.4, 9.3 Hz, 2H), 3.38 (s, 1H), 3.35 - 3.31 (m, 1H), 3.23 (d, J = 9.5 Hz, 1H), 3.11 (d, J = 9.5 Hz, 1H), 2.88 (dd, J = 13.5, 3.0 Hz, 1H), 2.03 (dd, J = 13.5, 10.3 Hz, 1H), 1.93 (d, J = 7.1Hz, 2H), 1.86 - 1.05 (m, 21H), 1.06 - 0.93 (m, 12H), 0.90 - 0.82 (m, 6H), 0.81 (d, J = 11.4 Hz, 1H). LRMS (ESI):689.43 [MH] - .

[0168] Example 93 (3S,5S,8R,9R,10S,14R,17R,18S)-28-O-(N-methyl)aminoethyl oleanolic acid-3-(1'R)-(hydroxy)methyl-β-D-glucuronopyranoside (A93) The remaining raw materials, reagents, and production method were the same as in Example 2, but with the exception of 2,3,4,6-O-tetrabenzyl-1-(pyridin-1-yl)sulfonyl-β-D-thioglucopyranoside being replaced with 2,3,4,6-O-tetrabenzyl-1-(pyridin-1-yl)sulfonyl-β-D-thioglucuronopyranoside, and (3S,5S,8R,9R,10S,14R,17R,18S)-28-O-benzyl-3-aldehyde oleanolic acid being replaced with (3S,5S,8R,9R,10S,14R,17R,18S)-28-O-(N-methyl)aminoethyl-3-aldehyde oleanolic acid. A93 (yield 69%) was obtained using the same method as in Example 2. 1H NMR (500 MHz, MeOD) δ 5.28 (s, 1H), 4.16 (s, 1H), 3.79 (d, J = 2.0 Hz, 2H), 3.46 (dd, J = 20.4, 9.3 Hz, 2H), 3.38 (s, 1H), 3.35 - 3.31 (m, 1H), 3.23 (d, J = 9.5 Hz, 1H), 3.11 (d, J = 9.5 Hz, 1H), 2.88 (dd, J = 13.5, 3.0 Hz, 1H), 2.03 (dd, J = 13.5, 10.3 Hz, 1H), 1.93 (d, J = 7.1Hz, 2H), 1.86 - 1.05 (m, 21H), 1.06 - 0.93 (m, 12H), 0.90 - 0.82 (m, 6H), 0.81 (d, J = 11.4 Hz, 1H). LRMS (ESI):702.47 [MH] - .

[0169] Example 94 (3S,5S,8R,9R,10S,14R,17R,18S)-28-O-(N,N-diethyl)aminoethyl oleanolic acid-3-(1'R)-(hydroxy)methyl-β-D-glucuronopyranoside (A94) The remaining raw materials, reagents, and production method were the same as in Example 2, but with the exception of 2,3,4,6-O-tetrabenzyl-1-(pyridin-1-yl)sulfonyl-β-D-thioglucopyranoside being replaced with 2,3,4,6-O-tetrabenzyl-1-(pyridin-1-yl)sulfonyl-β-D-thioglucuronopyranoside, and (3S,5S,8R,9R,10S,14R,17R,18S)-28-O-benzyl-3-aldehyde oleanolic acid being replaced with (3S,5S,8R,9R,10S,14R,17R,18S)-28-O-(N,N-diethyl)aminoethyl-3-aldehyde oleanolic acid. A94 (yield 68%) was obtained using the same method as in Example 2. 1H NMR (500 MHz, MeOD) δ 5.28 (s, 1H), 4.16 (s, 1H), 3.79 (d, J = 2.0 Hz, 2H), 3.46 (dd, J = 20.4, 9.3 Hz, 2H), 3.38 (s, 1H), 3.35 - 3.31 (m, 1H), 3.23 (d, J = 9.5 Hz, 1H), 3.11 (d, J = 9.5 Hz, 1H), 2.88 (dd, J = 13.5, 3.0 Hz, 1H), 2.03 (dd, J = 13.5, 10.3 Hz, 1H), 1.93 (d, J = 7.1Hz, 2H), 1.86 - 1.05 (m, 21H), 1.06 - 0.93 (m, 12H), 0.90 - 0.82 (m, 6H), 0.81 (d, J = 11.4 Hz, 1H). LRMS (ESI):744.51 [MH] - .

[0170] Example 95 (3S,5S,8R,9R,10S,14R,17R,18S)-28-O-hydroxybut-2'''-alkynyloleanolic acid-3-(1'R)-(hydroxy)methyl-β-D-glucuronopyranoside (A95) The same procedures were used with the remaining raw materials, reagents, and production method as in Example 2 to obtain A95 (yield 62%). 1H NMR (500 MHz, MeOD) δ 5.28 (s, 1H), 4.16 (s, 1H), 3.79 (d, J = 2.0 Hz, 2H), 3.46 (dd, J = 20.4, 9.3 Hz, 2H), 3.38 (s, 1H), 3.35 - 3.31 (m, 1H), 3.23 (d, J = 9.5 Hz, 1H), 3.11 (d, J = 9.5 Hz, 1H), 2.88 (dd, J = 13.5, 3.0 Hz, 1H), 2.03 (dd, J = 13.5, 10.3 Hz, 1H), 1.93 (d, J = 7.1Hz, 2H), 1.86 - 1.05 (m, 21H), 1.06 - 0.93 (m, 12H), 0.90 - 0.82 (m, 6H), 0.81 (d, J = 11.4 Hz, 1H). LRMS (ESI):713.43 [MH] - .

[0171] Example 96 (3S,5S,8R,9R,10S,14R,17R,18S)-28-O-cyclohexyloleanolic acid-3-(1'R)-(hydroxy)methyl-β-D-glucuronopyranoside (A96) The remaining raw materials, reagents, and production method were the same as in Example 2, but with the exception of 2,3,4,6-O-tetrabenzyl-1-(pyridin-1-yl)sulfonyl-β-D-thioglucopyranoside being replaced with 2,3,4,6-O-tetrabenzyl-1-(pyridin-1-yl)sulfonyl-β-D-thioglucuronopyranoside, and (3S,5S,8R,9R,10S,14R,17R,18S)-28-O-benzyl-3-aldehyde oleanolic acid being replaced with (3S,5S,8R,9R,10S,14R,17R,18S)-28-O-cyclohexyl-3-aldehyde oleanolic acid. A96 (yield 69%) was obtained using the same method as in Example 2. 1H NMR (500 MHz, MeOD) δ 5.28 (s, 1H), 4.16 (s, 1H), 3.79 (d, J = 2.0 Hz, 2H), 3.46 (dd, J = 20.4, 9.3 Hz, 2H), 3.38 (s, 1H), 3.35 - 3.31 (m, 1H), 3.23 (d, J = 9.5 Hz, 1H), 3.11 (d, J = 9.5 Hz, 1H), 2.88 (dd, J = 13.5, 3.0 Hz, 1H), 2.03 (dd, J = 13.5, 10.3 Hz, 1H), 1.93 (d, J = 7.1Hz, 2H), 1.86 - 1.05 (m, 21H), 1.06 - 0.93 (m, 12H), 0.90 - 0.82 (m, 6H), 0.81 (d, J = 11.4 Hz, 1H). LRMS (ESI):727.49 [MH] - .

[0172] Example 97 (3S,5S,8R,9R,10S,14R,17R,18S)-28-(O-methyl)carboxymethylaminooleanolic acid-3-(1'R)-(hydroxy)methyl-β-D-glucuronopyranoside (A97) The remaining raw materials, reagents, and production method were the same as in Example 2, but the compound A97 (yield 73%) was obtained. 1H NMR (500 MHz, MeOD) δ 5.28 (s, 1H), 4.16 (s, 1H), 3.79 (d, J = 2.0 Hz, 2H), 3.46 (dd, J = 20.4, 9.3 Hz, 2H), 3.38 (s, 1H), 3.35 - 3.31 (m, 1H), 3.23 (d, J = 9.5 Hz, 1H), 3.11 (d, J = 9.5 Hz, 1H), 2.88 (dd, J = 13.5, 3.0 Hz, 1H), 2.03 (dd, J = 13.5, 10.3 Hz, 1H), 1.93 (d, J = 7.1Hz, 2H), 1.86 - 1.05 (m, 21H), 1.06 - 0.93 (m, 12H), 0.90 - 0.82 (m, 6H), 0.81 (d, J = 11.4 Hz, 1H). LRMS (ESI):716.45 [MH] - .

[0173] Example 98 (3S,5S,8R,9R,10S,14R,17R,18S)-28-carboxymethylaminooleanolic acid-3-(1'R)-(hydroxy)methyl-β-D-glucuronopyranoside (A98) The remaining raw materials, reagents, and production method were the same as in Example 2, but with the exception of 2,3,4,6-O-tetrabenzyl-1-(pyridin-1-yl)sulfonyl-β-D-thioglucopyranoside being replaced with 2,3,4,6-O-tetrabenzyl-1-(pyridin-1-yl)sulfonyl-β-D-thioglucuronopyranoside, and (3S,5S,8R,9R,10S,14R,17R,18S)-28-O-benzyl-3-aldehyde oleanolic acid being replaced with (3S,5S,8R,9R,10S,14R,17R,18S)-28-O-carboxymethylamino-3-aldehyde oleanolic acid. A98 (yield 62%) was obtained using the same method as in Example 2. 1H NMR (500 MHz, MeOD) δ 5.28 (s, 1H), 4.16 (s, 1H), 3.79 (d, J = 2.0 Hz, 2H), 3.46 (dd, J = 20.4, 9.3 Hz, 2H), 3.38 (s, 1H), 3.35 - 3.31 (m, 1H), 3.23 (d, J = 9.5 Hz, 1H), 3.11 (d, J = 9.5 Hz, 1H), 2.88 (dd, J = 13.5, 3.0 Hz, 1H), 2.03 (dd, J = 13.5, 10.3 Hz, 1H), 1.93 (d, J = 7.1Hz, 2H), 1.86 - 1.05 (m, 21H), 1.06 - 0.93 (m, 12H), 0.90 - 0.82 (m, 6H), 0.81 (d, J = 11.4 Hz, 1H). LRMS (ESI):702.43 [MH] - .

[0174] Example 99 (3S,5S,8R,9R,10S,14R,17R,18S)-28-(N,N-diethyl)aminopropylaminooleanolic acid-3-(1'R)-(hydroxy)methyl-β-D-glucuronopyranoside (A99) The remaining raw materials, reagents, and production method were the same as in Example 2, but the compound A99 (yield 66%) was obtained. 1H NMR (500 MHz, MeOD) δ 5.28 (s, 1H), 4.16 (s, 1H), 3.79 (d, J = 2.0 Hz, 2H), 3.46 (dd, J = 20.4, 9.3 Hz, 2H), 3.38 (s, 1H), 3.35 - 3.31 (m, 1H), 3.23 (d, J = 9.5 Hz, 1H), 3.11 (d, J = 9.5 Hz, 1H), 2.88 (dd, J = 13.5, 3.0 Hz, 1H), 2.03 (dd, J = 13.5, 10.3 Hz, 1H), 1.93 (d, J = 7.1Hz, 2H), 1.86 - 1.05 (m, 21H), 1.06 - 0.93 (m, 12H), 0.90 - 0.82 (m, 6H), 0.81 (d, J = 11.4 Hz, 1H). LRMS (ESI):757.54 [MH] - .

[0175] Example 100 (3S,5S,8R,9R,10S,14R,17R,18S)-28-(N-acetyl)aminopropylaminooleanolic acid-3-(1'R)-(hydroxy)methyl-β-D-glucuronopyranoside (A100) The remaining raw materials, reagents, and production method were the same as in Example 2, but the compound A100 (yield 65%) was obtained using the same procedure as in Example 2. 1H NMR (500 MHz, MeOD) δ 5.28 (s, 1H), 4.16 (s, 1H), 3.79 (d, J = 2.0 Hz, 2H), 3.46 (dd, J = 20.4, 9.3 Hz, 2H), 3.38 (s, 1H), 3.35 - 3.31 (m, 1H), 3.23 (d, J = 9.5 Hz, 1H), 3.11 (d, J = 9.5 Hz, 1H), 2.88 (dd, J = 13.5, 3.0 Hz, 1H), 2.03 (dd, J = 13.5, 10.3 Hz, 1H), 1.93 (d, J = 7.1Hz, 2H), 1.86 - 1.05 (m, 21H), 1.06 - 0.93 (m, 12H), 0.90 - 0.82 (m, 6H), 0.81 (d, J = 11.4 Hz, 1H). LRMS (ESI):743.49 [MH] - .

[0176] Example 101 (3S,5S,8R,9R,10S,14R,17R,18S)-28-(N,N-diethyl)aminohexylaminooleanolic acid-3-(1'R)-(hydroxy)methyl-β-D-glucuronopyranoside (A101) The remaining raw materials, reagents, and production method were the same as in Example 2, but the compound A101 (yield 71%) was obtained. 1H NMR (500 MHz, MeOD) δ 5.28 (s, 1H), 4.16 (s, 1H), 3.79 (d, J = 2.0 Hz, 2H), 3.46 (dd, J = 20.4, 9.3 Hz, 2H), 3.38 (s, 1H), 3.35 - 3.31 (m, 1H), 3.23 (d, J = 9.5 Hz, 1H), 3.11 (d, J = 9.5 Hz, 1H), 2.88 (dd, J = 13.5, 3.0 Hz, 1H), 2.03 (dd, J = 13.5, 10.3 Hz, 1H), 1.93 (d, J = 7.1Hz, 2H), 1.86 - 1.05 (m, 21H), 1.06 - 0.93 (m, 12H), 0.90 - 0.82 (m, 6H), 0.81 (d, J = 11.4 Hz, 1H). LRMS (ESI):799.59 [MH] - .

[0177] Example 102 (3S,5S,8R,9R,10S,14R,17R,18S)-28-(N-acetyl)aminohexylaminooleanolic acid-3-(1'R)-(hydroxy)methyl-β-D-glucuronopyranoside (A102) The remaining raw materials, reagents, and production method were the same as in Example 2, but the compound A102 (yield 68%) was obtained. 1H NMR (500 MHz, MeOD) δ 5.28 (s, 1H), 4.16 (s, 1H), 3.79 (d, J = 2.0 Hz, 2H), 3.46 (dd, J = 20.4, 9.3 Hz, 2H), 3.38 (s, 1H), 3.35 - 3.31 (m, 1H), 3.23 (d, J = 9.5 Hz, 1H), 3.11 (d, J = 9.5 Hz, 1H), 2.88 (dd, J = 13.5, 3.0 Hz, 1H), 2.03 (dd, J = 13.5, 10.3 Hz, 1H), 1.93 (d, J = 7.1Hz, 2H), 1.86 - 1.05 (m, 21H), 1.06 - 0.93 (m, 12H), 0.90 - 0.82 (m, 6H), 0.81 (d, J = 11.4 Hz, 1H). LRMS (ESI):785.54 [MH] - .

[0178] Example 103 (3S,5S,8R,9R,10S,14R,17R,18S)-28-(N-ethyl)aminohexylaminooleanolic acid-3-(1'R)-(hydroxy)methyl-β-D-glucuronopyranoside (A103) The remaining raw materials, reagents, and production method were the same as in Example 2, but the compound A103 (yield 69%) was obtained using the same procedure as in Example 2. The compound A103 was obtained using the same procedure as in Example 2, except that 2,3,4,6-O-tetrabenzyl-1-(pyridin-1-yl)sulfonyl-β-D-thioglucuronopyranoside was used instead of 2,3,4,6-O-tetrabenzyl-1-(pyridin-1-yl)sulfonyl-β-D-thioglucuronopyranoside, and (3S,5S,8R,9R,10S,14R,17R,18S)-28-O-benzyl-3-aldehyde oleanolic acid was used instead of (3S,5S,8R,9R,10S,14R,17R,18S)-28-O-(N-ethyl)aminohexylamino-3-aldehyde oleanolic acid. 1H NMR (500 MHz, MeOD) δ 5.28 (s, 1H), 4.16 (s, 1H), 3.79 (d, J = 2.0 Hz, 2H), 3.46 (dd, J = 20.4, 9.3 Hz, 2H), 3.38 (s, 1H), 3.35 - 3.31 (m, 1H), 3.23 (d, J = 9.5 Hz, 1H), 3.11 (d, J = 9.5 Hz, 1H), 2.88 (dd, J = 13.5, 3.0 Hz, 1H), 2.03 (dd, J = 13.5, 10.3 Hz, 1H), 1.93 (d, J = 7.1Hz, 2H), 1.86 - 1.05 (m, 21H), 1.06 - 0.93 (m, 12H), 0.90 - 0.82 (m, 6H), 0.81 (d, J = 11.4 Hz, 1H). LRMS (ESI):771.56 [MH] - .

[0179] Example 104 (3S,5S,8R,9R,10S,14R,17R,18S)-28-O-(pyrazol-1″-yl)methyl oleanolic acid-3-(1′R)-(hydroxy)methyl-β-D-glucuronopyranoside (A104) The remaining raw materials, reagents, and preparation method were the same as in Example 2, but the compound A104 (yield 65%) was obtained. 1H NMR (500 MHz, MeOD) δ 5.28 (s, 1H), 4.16 (s, 1H), 3.79 (d, J = 2.0 Hz, 2H), 3.46 (dd, J = 20.4, 9.3 Hz, 2H), 3.38 (s, 1H), 3.35 - 3.31 (m, 1H), 3.23 (d, J = 9.5 Hz, 1H), 3.11 (d, J = 9.5 Hz, 1H), 2.88 (dd, J = 13.5, 3.0 Hz, 1H), 2.03 (dd, J = 13.5, 10.3 Hz, 1H), 1.93 (d, J = 7.1Hz, 2H), 1.86 - 1.05 (m, 21H), 1.06 - 0.93 (m, 12H), 0.90 - 0.82 (m, 6H), 0.81 (d, J = 11.4 Hz, 1H). LRMS (ESI):725.45 [MH] - .

[0180] Example 105 (3S,5S,8R,9R,10S,14R,17R,18S)-28-O-(piperidin-1″-yl)methyl oleanolic acid-3-(1′R)-(hydroxy)methyl-β-D-glucuronopyranoside (A105) The remaining raw materials, reagents, and production method were the same as in Example 2, but A105 (yield 70%) was obtained. 1H NMR (500 MHz, MeOD) δ 5.28 (s, 1H), 4.16 (s, 1H), 3.79 (d, J = 2.0 Hz, 2H), 3.46 (dd, J = 20.4, 9.3 Hz, 2H), 3.38 (s, 1H), 3.35 - 3.31 (m, 1H), 3.23 (d, J = 9.5 Hz, 1H), 3.11 (d, J = 9.5 Hz, 1H), 2.88 (dd, J = 13.5, 3.0 Hz, 1H), 2.03 (dd, J = 13.5, 10.3 Hz, 1H), 1.93 (d, J = 7.1Hz, 2H), 1.86 - 1.05 (m, 21H), 1.06 - 0.93 (m, 12H), 0.90 - 0.82 (m, 6H), 0.81 (d, J = 11.4 Hz, 1H). LRMS (ESI):756.51 [MH] - .

[0181] Example 106 (3S,5S,8R,9R,10S,14R,17R,18S)-28-O-(morpholin-4″-yl)methyl oleanolic acid-3-(1′R)-(hydroxy)methyl-β-D-glucuronopyranoside (A106) The remaining raw materials, reagents, and preparation method were the same as in Example 2, but with the exception of 2,3,4,6-O-tetrabenzyl-1-(pyridin-1-yl)sulfonyl-β-D-thioglucopyranoside being replaced with 2,3,4,6-O-tetrabenzyl-1-(pyridin-1-yl)sulfonyl-β-D-thioglucuronopyranoside, and (3S,5S,8R,9R,10S,14R,17R,18S)-28-O-benzyl-3-aldehyde oleanolic acid being replaced with (3S,5S,8R,9R,10S,14R,17R,18S)-28-O-(morpholin-4-yl)methyl-3-aldehyde oleanolic acid. A106 (yield 67%) was obtained using the same method as in Example 2. 1H NMR (500 MHz, MeOD) δ 5.28 (s, 1H), 4.16 (s, 1H), 3.79 (d, J = 2.0 Hz, 2H), 3.46 (dd, J = 20.4, 9.3 Hz, 2H), 3.38 (s, 1H), 3.35 - 3.31 (m, 1H), 3.23 (d, J = 9.5 Hz, 1H), 3.11 (d, J = 9.5 Hz, 1H), 2.88 (dd, J = 13.5, 3.0 Hz, 1H), 2.03 (dd, J = 13.5, 10.3 Hz, 1H), 1.93 (d, J = 7.1Hz, 2H), 1.86 - 1.05 (m, 21H), 1.06 - 0.93 (m, 12H), 0.90 - 0.82 (m, 6H), 0.81 (d, J = 11.4 Hz, 1H). LRMS (ESI):758.49 [MH] - .

[0182] Example 107 (3S,5S,8R,9R,10S,14R,17R,18S)-Oleanolic acid-3-(1'R)-fluoromethyl-β-D-glucuronopyranoside (A107) [ka]

[0183] The remaining raw materials, reagents, and preparation method were the same as in Example 10, but the compound A107 (yield 65%) was obtained using the same procedure as in Example 10, except that 2,3,4,6-O-tetrabenzyl-1-(pyridin-1-yl)sulfonyl-β-D-thioglucuronopyranoside was replaced with 2,3,4,6-O-tetrabenzyl-1-(pyridin-1-yl)sulfonyl-β-D-thioglucuronopyranoside and Dess-Martin reagent was replaced with DAST. 1H NMR (500 MHz, MeOD) δ 5.28 (s, 1H), 4.16 (s, 1H), 3.79 (d, J = 2.0 Hz, 2H), 3.46 (dd, J = 20.4, 9.3 Hz, 2H), 3.38 (s, 1H), 3.35 - 3.31 (m, 1H), 3.23 (d, J = 9.5 Hz, 1H), 3.11 (d, J = 9.5 Hz, 1H), 2.88 (dd, J = 13.5, 3.0 Hz, 1H), 2.03 (dd, J = 13.5, 10.3 Hz, 1H), 1.93 (d, J = 7.1Hz, 2H), 1.86 - 1.05 (m, 21H), 1.06 - 0.93 (m, 12H), 0.90 - 0.82 (m, 6H), 0.81 (d, J = 11.4 Hz, 1H). LRMS (ESI):647.40 [MH] - .

[0184] Example 108 (3S,5S,8R,9R,10S,14R,17R,18S)-Oleanolic acid-3-(1'R)-(hydroxy)methyl-28-(1''R)-(hydroxy)methyl-β-D-diglucuronopyranoside (A108) The remaining raw materials, reagents, and production method were the same as in Example 2, but with the exception of 2,3,4,6-O-tetrabenzyl-1-(pyridin-1-yl)sulfonyl-β-D-thioglucopyranoside being replaced with 2,3,4,6-O-tetrabenzyl-1-(pyridin-1-yl)sulfonyl-β-D-thioglucuronopyranoside, and (3S,5S,8R,9R,10S,14R,17R,18S)-28-O-benzyl-3-aldehyde oleanolic acid being replaced with (3S,5S,8R,9R,10S,14R,17R,18S)-3,17-dialdehyde oleanolic acid. A108 (yield 62%) was obtained using the same method as in Example 2. 1H NMR (500 MHz, MeOD) δ 5.28 (s, 1H), 4.16 (s, 1H), 3.79 (d, J = 2.0 Hz, 4H), 3.46 (dd, J = 20.4, 9.3 Hz, 4H), 3.38 (s, 2H), 3.35 - 3.31 (m, 2H), 3.23 (d, J = 9.5 Hz, 2H), 3.11 (d, J = 9.5 Hz, 2H), 2.88 (dd, J = 13.5, 3.0 Hz, 1H), 2.03 (dd, J = 13.5, 10.3 Hz, 1H), 1.93 (d, J = 7.1Hz, 2H), 1.86 - 1.05 (m, 21H), 1.06 - 0.93 (m, 12H), 0.90 - 0.82 (m, 6H), 0.81 (d, J = 11.4 Hz, 1H). LRMS (ESI):807.46 [MH] - .

[0185] Example 109 (3S,5S,8R,9R,10S,14R,17R,18S)-Oleanolic acid-3-(1'R)-(hydroxy)methyl-6''-O-methyl-β-D-glucuronopyranoside (A109) The remaining raw materials, reagents, and production method were the same as in Example 2, except that 2,3,4,6-O-tetrabenzyl-1-(pyridin-1-yl)sulfonyl-β-D-thioglucopyranoside was replaced with 2,3,4,6-O-tetrabenzyl-1-(pyridin-1-yl)sulfonyl-6-O-methyl-β-D-thioglucuronopyranoside. A109 (yield 71%) was obtained using the same method as in Example 2. 1H NMR (500 MHz, MeOD) δ 5.28 (s, 1H), 4.16 (s, 1H), 3.79 (d, J = 2.0 Hz, 2H), 3.46 (dd, J = 20.4, 9.3 Hz, 2H), 3.38 (s, 1H), 3.35 - 3.31 (m, 1H), 3.23 (d, J = 9.5 Hz, 1H), 3.11 (d, J = 9.5 Hz, 1H), 2.88 (dd, J = 13.5, 3.0 Hz, 1H), 2.03 (dd, J = 13.5, 10.3 Hz, 1H), 1.93 (d, J = 7.1Hz, 2H), 1.86 - 1.05 (m, 21H), 1.06 - 0.93 (m, 12H), 0.90 - 0.82 (m, 6H), 0.81 (d, J = 11.4 Hz, 1H). LRMS (ESI):659.42 [MH] - .

[0186] Example 110 (3S,5S,8R,9R,10S,14R,17R,18S)-Oleanolic acid-3-(1'R)-(hydroxy)methyl-6''-on-butyl-β-D-glucuronopyranoside (A110) The remaining raw materials, reagents, and production method were the same as in Example 2, except that 2,3,4,6-O-tetrabenzyl-1-(pyridin-1-yl)sulfonyl-β-D-thioglucopyranoside was replaced with 2,3,4,6-O-tetrabenzyl-1-(pyridin-1-yl)sulfonyl-6-on-butyl-β-D-thioglucuronopyranoside. A110 (yield 71%) was obtained using the same method as in Example 2. 1H NMR (500 MHz, MeOD) δ 5.28 (s, 1H), 4.16 (s, 1H), 3.79 (d, J = 2.0 Hz, 2H), 3.46 (dd, J = 20.4, 9.3 Hz, 2H), 3.38 (s, 1H), 3.35 - 3.31 (m, 1H), 3.23 (d, J = 9.5 Hz, 1H), 3.11 (d, J = 9.5 Hz, 1H), 2.88 (dd, J = 13.5, 3.0 Hz, 1H), 2.03 (dd, J = 13.5, 10.3 Hz, 1H), 1.93 (d, J = 7.1Hz, 2H), 1.86 - 1.05 (m, 21H), 1.06 - 0.93 (m, 12H), 0.90 - 0.82 (m, 6H), 0.81 (d, J = 11.4 Hz, 1H). LRMS (ESI):701.47 [MH] - .

[0187] Example 111 (3S,5S,8R,9R,10S,14R,17R,18S)-Oleanolic acid-3-(1'R)-(hydroxy)methyl-6''-O-isobutyl-β-D-glucuronopyranoside (A111) The remaining raw materials, reagents, and production method were the same as in Example 2, except that 2,3,4,6-O-tetrabenzyl-1-(pyridin-1-yl)sulfonyl-β-D-thioglucopyranoside was replaced with 2,3,4,6-O-tetrabenzyl-1-(pyridin-1-yl)sulfonyl-6-O-isobutyl-β-D-thioglucuronopyranoside. A111 (yield 61%) was obtained using the same method as in Example 2. 1H NMR (500 MHz, MeOD) δ 5.28 (s, 1H), 4.16 (s, 1H), 3.79 (d, J = 2.0 Hz, 2H), 3.46 (dd, J = 20.4, 9.3 Hz, 2H), 3.38 (s, 1H), 3.35 - 3.31 (m, 1H), 3.23 (d, J = 9.5 Hz, 1H), 3.11 (d, J = 9.5 Hz, 1H), 2.88 (dd, J = 13.5, 3.0 Hz, 1H), 2.03 (dd, J = 13.5, 10.3 Hz, 1H), 1.93 (d, J = 7.1Hz, 2H), 1.86 - 1.05 (m, 21H), 1.06 - 0.93 (m, 12H), 0.90 - 0.82 (m, 6H), 0.81 (d, J = 11.4 Hz, 1H). LRMS (ESI):701.47 [MH] - .

[0188] Example 112 (3S,5S,8R,9R,10S,14R,17R,18S)-Oleanolic acid-3-(1'R)-(hydroxy)methyl-6''-O-benzyl-β-D-glucuronopyranoside (A112) The remaining raw materials, reagents, and production method were the same as in Example 2, except that 2,3,4,6-O-tetrabenzyl-1-(pyridin-1-yl)sulfonyl-β-D-thioglucuronopyranoside was used instead of 2,3,4,6-O-tetrabenzyl-1-(pyridin-1-yl)sulfonyl-6-O-benzyl-β-D-thioglucuronopyranoside. A112 (yield 68%) was obtained using the same method as in Example 2. 1H NMR (500 MHz, MeOD) δ 7.32 (m, 5H), 5.28 (s, 1H), 4.16 (s, 1H), 3.79 (d, J = 2.0 Hz, 2H), 3.46 (dd, J = 20.4, 9.3 Hz, 2H), 3.38 (s, 1H), 3.35 - 3.31 (m, 1H), 3.23 (d, J = 9.5 Hz, 1H), 3.11 (d, J = 9.5 Hz, 1H), 2.88 (dd, J = 13.5, 3.0 Hz, 1H), 2.03 (dd, J = 13.5, 10.3 Hz, 1H), 1.93 (d, J = 7.1 Hz, 2H), 1.86 - 1.05 (m, 21H), 1.06 - 0.93 (m, 12H), 0.90 - 0.82 (m, 6H), 0.81 (d, J = 11.4 Hz, 1H). LRMS (ESI):735.46 [MH] - .

[0189] Example 113 (3S,5S,8R,9R,10S,14R,17R,18S)-Oleanolic acid-3-(1'R)-(hydroxy)methyl-6''-O-(1-fluoroacetyl)-β-D-glucuronopyranoside (A113) 2,3,4,6-O-tetrabenzyl-1-(pyridin-1-yl)sulfonyl-β-D-thioglucopyranoside was replaced with 2,3,4,6-O-tetrabenzyl-1-(pyridin-1-yl)sulfonyl-6"-O-(1-fluoroacetyl)-β-D-thioglucuronopyranoside. The remaining raw materials, reagents, and production method were the same as in Example 2, and A113 (yield 72%) was obtained. 1H NMR (500 MHz, MeOD) δ 5.28 (s, 1H), 4.16 (s, 1H), 3.79 (d, J = 2.0 Hz, 2H), 3.46 (dd, J = 20.4, 9.3 Hz, 2H), 3.38 (s, 1H), 3.35 - 3.31 (m, 1H), 3.23 (d, J = 9.5 Hz, 1H), 3.11 (d, J = 9.5 Hz, 1H), 2.88 (dd, J = 13.5, 3.0 Hz, 1H), 2.03 (dd, J = 13.5, 10.3 Hz, 1H), 1.93 (d, J = 7.1Hz, 2H), 1.86 - 1.05 (m, 21H), 1.06 - 0.93 (m, 12H), 0.90 - 0.82 (m, 6H), 0.81 (d, J = 11.4 Hz, 1H). LRMS (ESI):658.44 [MH] - .

[0190] Example 114 (3S,5S,8R,9R,10S,14R,17R,18S)-Oleanolic acid-3-(1'R)-(hydroxy)methyl-6''-methylamino-β-D-glucuronopyranoside (A114) The remaining raw materials, reagents, and production method were the same as in Example 2, except that 2,3,4,6-O-tetrabenzyl-1-(pyridin-1-yl)sulfonyl-β-D-thioglucopyranoside was replaced with 2,3,4,6-O-tetrabenzyl-1-(pyridin-1-yl)sulfonyl-6-methylamino-β-D-thioglucuronopyranoside. A114 (yield 72%) was obtained using the same method as in Example 2. 1H NMR (500 MHz, MeOD) δ 5.28 (s, 1H), 4.16 (s, 1H), 3.79 (d, J = 2.0 Hz, 2H), 3.46 (dd, J = 20.4, 9.3 Hz, 2H), 3.38 (s, 1H), 3.35 - 3.31 (m, 1H), 3.23 (d, J = 9.5 Hz, 1H), 3.11 (d, J = 9.5 Hz, 1H), 2.88 (dd, J = 13.5, 3.0 Hz, 1H), 2.03 (dd, J = 13.5, 10.3 Hz, 1H), 1.93 (d, J = 7.1Hz, 2H), 1.86 - 1.05 (m, 21H), 1.06 - 0.93 (m, 12H), 0.90 - 0.82 (m, 6H), 0.81 (d, J = 11.4 Hz, 1H). LRMS (ESI):658.44 [MH] - .

[0191] Example 115 (3S,5S,8R,9R,10S,14R,17R,18S)-Oleanolic acid-3-(1'R)-(hydroxy)methyl-6''-n-butylamino-β-D-glucuronopyranoside (A115) The remaining raw materials, reagents, and production method were the same as in Example 2, except that 2,3,4,6-O-tetrabenzyl-1-(pyridin-1-yl)sulfonyl-β-D-thioglucopyranoside was replaced with 2,3,4,6-O-tetrabenzyl-1-(pyridin-1-yl)sulfonyl-6-n-butylamino-β-D-thioglucuronopyranoside. A115 (yield 70%) was obtained using the same method as in Example 2. 1H NMR (500 MHz, MeOD) δ 5.28 (s, 1H), 4.16 (s, 1H), 3.79 (d, J = 2.0 Hz, 2H), 3.46 (dd, J = 20.4, 9.3 Hz, 2H), 3.38 (s, 1H), 3.35 - 3.31 (m, 1H), 3.23 (d, J = 9.5 Hz, 1H), 3.11 (d, J = 9.5 Hz, 1H), 2.88 (dd, J = 13.5, 3.0 Hz, 1H), 2.03 (dd, J = 13.5, 10.3 Hz, 1H), 1.93 (d, J = 7.1Hz, 2H), 1.86 - 1.05 (m, 21H), 1.06 - 0.93 (m, 12H), 0.90 - 0.82 (m, 6H), 0.81 (d, J = 11.4 Hz, 1H). LRMS (ESI):600.49 [MH] - .

[0192] Example 116 (3S,5S,8R,9R,10S,14R,17R,18S)-Oleanolic acid-3-(1'R)-(hydroxy)methyl-6''-isobutylamino-β-D-glucuronopyranoside (A116) The remaining raw materials, reagents, and production method were the same as in Example 2, except that 2,3,4,6-O-tetrabenzyl-1-(pyridin-1-yl)sulfonyl-β-D-thioglucuronopyranoside was used instead of 2,3,4,6-O-tetrabenzyl-1-(pyridin-1-yl)sulfonyl-6-isobutylamino-β-D-thioglucuronopyranoside. A116 (yield 80%) was obtained using the same method as in Example 2. 1H NMR (500 MHz, MeOD) δ 5.28 (s, 1H), 4.16 (s, 1H), 3.79 (d, J = 2.0 Hz, 2H), 3.46 (dd, J = 20.4, 9.3 Hz, 2H), 3.38 (s, 1H), 3.35 - 3.31 (m, 1H), 3.23 (d, J = 9.5 Hz, 1H), 3.11 (d, J = 9.5 Hz, 1H), 2.88 (dd, J = 13.5, 3.0 Hz, 1H), 2.03 (dd, J = 13.5, 10.3 Hz, 1H), 1.93 (d, J = 7.1Hz, 2H), 1.86 - 1.05 (m, 21H), 1.06 - 0.93 (m, 12H), 0.90 - 0.82 (m, 6H), 0.81 (d, J = 11.4 Hz, 1H). LRMS (ESI):700.49 [MH] - .

[0193] Example 117 (3S,5S,8R,9R,10S,14R,17R,18S)-Oleanolic acid-3-(1'R)-(hydroxy)methyl-6''-benzylamino-β-D-glucuronopyranoside (A117) The remaining raw materials, reagents, and production method were the same as in Example 2, except that 2,3,4,6-O-tetrabenzyl-1-(pyridin-1-yl)sulfonyl-β-D-thioglucuronopyranoside was used instead of 2,3,4,6-O-tetrabenzyl-1-(pyridin-1-yl)sulfonyl-6-benzylamino-β-D-thioglucuronopyranoside. A117 (yield 82%) was obtained using the same method as in Example 2. 1H NMR (500 MHz, MeOD) δ 7.33(m, 5H), 5.28 (s, 1H), 4.16 (s, 1H), 3.79 (d, J = 2.0 Hz, 2H), 3.46 (dd, J = 20.4, 9.3 Hz, 2H), 3.38 (s, 1H), 3.35 - 3.31 (m, 1H), 3.23 (d, J = 9.5 Hz, 1H), 3.11 (d, J = 9.5 Hz, 1H), 2.88 (dd, J = 13.5, 3.0 Hz, 1H), 2.03 (dd, J = 13.5, 10.3 Hz, 1H), 1.93 (d, J = 7.1 Hz, 2H), 1.86 - 1.05 (m, 21H), 1.06 - 0.93 (m, 12H), 0.90 - 0.82 (m, 6H), 0.81 (d, J = 11.4 Hz, 1H). LRMS (ESI):734.47 [MH] - .

[0194] Example 118 (3S,5S,8R,9R,10S,14R,17R,18S)-Oleanolic acid-3-(1'R)-(hydroxy)methyl-6''-dimethylamino-β-D-glucuronopyranoside (A118) The remaining raw materials, reagents, and production method were the same as in Example 2, except that 2,3,4,6-O-tetrabenzyl-1-(pyridin-1-yl)sulfonyl-β-D-thioglucopyranoside was replaced with 2,3,4,6-O-tetrabenzyl-1-(pyridin-1-yl)sulfonyl-6-dimethylamino-β-D-thioglucuronopyranoside. A118 (yield 72%) was obtained using the same method as in Example 2. 1H NMR (500 MHz, MeOD) δ 5.28 (s, 1H), 4.16 (s, 1H), 3.79 (d, J = 2.0 Hz, 2H), 3.46 (dd, J = 20.4, 9.3 Hz, 2H), 3.38 (s, 1H), 3.35 - 3.31 (m, 1H), 3.23 (d, J = 9.5 Hz, 1H), 3.11 (d, J = 9.5 Hz, 1H), 2.88 (dd, J = 13.5, 3.0 Hz, 1H), 2.03 (dd, J = 13.5, 10.3 Hz, 1H), 1.93 (d, J = 7.1Hz, 2H), 1.86 - 1.05 (m, 21H), 1.06 - 0.93 (m, 12H), 0.90 - 0.82 (m, 6H), 0.81 (d, J = 11.4 Hz, 1H). LRMS (ESI):672.46 [MH] - .

[0195] Example 119 (3S,5S,8R,9R,10S,14R,17R,18S)-Oleanolic acid-3-(1'R)-(hydroxy)methyl-6''-(1-fluoroethylamino)-β-D-glucuronopyranoside (A119) The remaining raw materials, reagents, and production method were the same as in Example 2, except that 2,3,4,6-O-tetrabenzyl-1-(pyridin-1-yl)sulfonyl-β-D-thioglucopyranoside was replaced with 2,3,4,6-O-tetrabenzyl-1-(pyridin-1-yl)sulfonyl-6-(1-fluoroethylamino)-β-D-thioglucuronopyranoside. A119 (yield 72%) was obtained using the same method as in Example 2. 1H NMR (500 MHz, MeOD) δ 5.28 (s, 1H), 4.16 (s, 1H), 3.79 (d, J = 2.0 Hz, 2H), 3.46 (dd, J = 20.4, 9.3 Hz, 2H), 3.38 (s, 1H), 3.35 - 3.31 (m, 1H), 3.23 (d, J = 9.5 Hz, 1H), 3.11 (d, J = 9.5 Hz, 1H), 2.88 (dd, J = 13.5, 3.0 Hz, 1H), 2.03 (dd, J = 13.5, 10.3 Hz, 1H), 1.93 (d, J = 7.1Hz, 2H), 1.86 - 1.05 (m, 21H), 1.06 - 0.93 (m, 12H), 0.90 - 0.82 (m, 6H), 0.81 (d, J = 11.4 Hz, 1H). LRMS (ESI):672.46 [MH] - .

[0196] Example 120 (3S,5S,8R,9R,10S,14R,17R,18S)-Oleanolic acid-3-(1'R)-(hydroxy)methyl-5''-cyano-β-D-xylopyranoside (A120) The remaining raw materials, reagents, and production method were the same as in Example 2, except that 2,3,4,6-O-tetrabenzyl-1-(pyridin-1-yl)sulfonyl-β-D-thioglucopyranoside was replaced with 2,3,4,6-O-tetrabenzyl-1-(pyridin-1-yl)sulfonyl-5-cyano-β-D-thioxilopyranoside. A120 (yield 78%) was obtained using the same method as in Example 2. 1H NMR (500 MHz, MeOD) δ 5.28 (s, 1H), 4.16 (s, 1H), 3.79 (d, J = 2.0 Hz, 2H), 3.46 (dd, J = 20.4, 9.3 Hz, 2H), 3.38 (s, 1H), 3.35 - 3.31 (m, 1H), 3.23 (d, J = 9.5 Hz, 1H), 3.11 (d, J = 9.5 Hz, 1H), 2.88 (dd, J = 13.5, 3.0 Hz, 1H), 2.03 (dd, J = 13.5, 10.3 Hz, 1H), 1.93 (d, J = 7.1Hz, 2H), 1.86 - 1.05 (m, 21H), 1.06 - 0.93 (m, 12H), 0.90 - 0.82 (m, 6H), 0.81 (d, J = 11.4 Hz, 1H). LRMS (ESI):626.41 [MH] - .

[0197] Example 121 (5S,8R,9R,10S,14R,17R,18S)-3-carbonyloleanolic acid-17-(1'S)-(hydroxy)methyl-β-D-mannopyranoside (A121) The remaining raw materials, reagents, and production method were the same as in Example 6, but A121 (yield 69%) was obtained. 1H NMR (500 MHz, MeOD) δ 5.28 (s, 1H), 4.16 (s, 1H), 3.79 (d, J = 2.0 Hz, 2H), 3.46 (dd, J = 20.4, 9.3 Hz, 2H), 3.38 (s, 1H), 3.35 - 3.31 (m, 1H), 3.23 (d, J = 9.5 Hz, 1H), 3.11 (d, J = 9.5 Hz, 1H), 2.88 (dd, J = 13.5, 3.0 Hz, 1H), 2.03 (dd, J = 13.5, 10.3 Hz, 1H), 1.93 (d, J = 7.1Hz, 2H), 1.86 - 1.05 (m, 21H), 1.06 - 0.93 (m, 12H), 0.90 - 0.82 (m, 6H), 0.81 (d, J = 11.4 Hz, 1H). LRMS (ESI):603.42 [M+H] + .

[0198] Example 122 (3S,5S,8R,9R,10S,14R,17R,18S)-oleanolic acid-17-(1'S)-(hydroxy)methyl-β-D-mannopyranoside (A122) The remaining raw materials, reagents, and production method were the same as in Example 6, but with the exception of 2,3,4,6-O-tetrabenzyl-1-(pyridin-1-yl)sulfonyl-β-D-thioglucopyranoside being replaced with 2,3,4,6-O-tetrabenzyl-1-(pyridin-1-yl)sulfonyl-β-D-thiomannopyranoside, and (3S,5S,8R,9R,10S,14R,17R,18S)-28-O-benzyl-3-aldehyde oleanolic acid being replaced with (5S,8R,9R,10S,14R,17R,18S)-3-hydroxy-17-aldehyde oleanolic acid. A122 (73% yield) was obtained using the same method as in Example 6, using the same starting materials, reagents, and production method as in Example 6. 1H NMR (500 MHz, MeOD) δ 5.28 (s, 1H), 4.16 (s, 1H), 3.79 (d, J = 2.0 Hz, 2H), 3.46 (dd, J = 20.4, 9.3 Hz, 2H), 3.38 (s, 1H), 3.35 - 3.31 (m, 1H), 3.23 (d, J = 9.5 Hz, 1H), 3.11 (d, J = 9.5 Hz, 1H), 2.88 (dd, J = 13.5, 3.0 Hz, 1H), 2.03 (dd, J = 13.5, 10.3 Hz, 1H), 1.93 (d, J = 7.1Hz, 2H), 1.86 - 1.05 (m, 21H), 1.06 - 0.93 (m, 12H), 0.90 - 0.82 (m, 6H), 0.81 (d, J = 11.4 Hz, 1H). LRMS (ESI):605.43 [M+H] + .

[0199] Example 123 (3S,5S,8R,9R,10S,14R,17R,18S)-3-Methoxyoleanolic acid-17-(1'S)-(hydroxy)methyl-β-D-mannopyranoside (A123) The remaining raw materials, reagents, and production method were the same as in Example 6, but A123 (yield 70%) was obtained. 1H NMR (500 MHz, MeOD) δ 5.28 (s, 1H), 4.16 (s, 1H), 3.79 (d, J = 2.0 Hz, 2H), 3.46 (dd, J = 20.4, 9.3 Hz, 2H), 3.38 (s, 1H), 3.35 - 3.31 (m, 1H), 3.23 (d, J = 9.5 Hz, 1H), 3.11 (d, J = 9.5 Hz, 1H), 2.88 (dd, J = 13.5, 3.0 Hz, 1H), 2.03 (dd, J = 13.5, 10.3 Hz, 1H), 1.93 (d, J = 7.1Hz, 2H), 1.86 - 1.05 (m, 21H), 1.06 - 0.93 (m, 12H), 0.90 - 0.82 (m, 6H), 0.81 (d, J = 11.4 Hz, 1H). LRMS (ESI):619.45 [M+H] + .

[0200] Example 124 (3S,5S,8R,9R,10S,14R,17R,18S)-3-(4-fluorocyclohexyloxy)oleanolic acid-17-(1'S)-(hydroxy)methyl-β-D-mannopyranoside (A124) The remaining raw materials, reagents, and preparation method were the same as in Example 6, but with the exception of 2,3,4,6-O-tetrabenzyl-1-(pyridin-1-yl)sulfonyl-β-D-thioglucopyranoside, which was replaced with 2,3,4,6-O-tetrabenzyl-1-(pyridin-1-yl)sulfonyl-β-D-thiomannopyranoside, and (3S,5S,8R,9R,10S,14R,17R,18S)-28-O-benzyl-3-aldehyde oleanolic acid, which was replaced with (5S,8R,9R,10S,14R,17R,18S)-3-(4-fluorocyclohexyloxy)-17-aldehyde oleanolic acid. A124 (72% yield) was obtained using the same method as in Example 6. 1H NMR (500 MHz, MeOD) δ 5.28 (s, 1H), 4.16 (s, 1H), 3.79 (d, J = 2.0 Hz, 2H), 3.46 (dd, J = 20.4, 9.3 Hz, 2H), 3.38 (s, 1H), 3.35 - 3.31 (m, 1H), 3.23 (d, J = 9.5 Hz, 1H), 3.11 (d, J = 9.5 Hz, 1H), 2.88 (dd, J = 13.5, 3.0 Hz, 1H), 2.03 (dd, J = 13.5, 10.3 Hz, 1H), 1.93 (d, J = 7.1Hz, 2H), 1.86 - 1.05 (m, 21H), 1.06 - 0.93 (m, 12H), 0.90 - 0.82 (m, 6H), 0.81 (d, J = 11.4 Hz, 1H). LRMS (ESI):705.50 [M+H] + .

[0201] Example 125 (3S,5S,8R,9R,10S,14R,17R,18S)-3-acetoxyoleanolic acid-17-(1'S)-(hydroxy)methyl-β-D-mannopyranoside (A125) The remaining raw materials, reagents, and production method were the same as in Example 6, but with the exception of 2,3,4,6-O-tetrabenzyl-1-(pyridin-1-yl)sulfonyl-β-D-thioglucopyranoside being replaced with 2,3,4,6-O-tetrabenzyl-1-(pyridin-1-yl)sulfonyl-β-D-thiomannopyranoside, and (3S,5S,8R,9R,10S,14R,17R,18S)-28-O-benzyl-3-aldehyde oleanolic acid being replaced with (5S,8R,9R,10S,14R,17R,18S)-3-acetoxy-17-aldehyde oleanolic acid. A125 (77% yield) was obtained using the same method as in Example 6, using the same raw materials, reagents, and production method as in Example 6. 1H NMR (500 MHz, MeOD) δ 5.28 (s, 1H), 4.16 (s, 1H), 3.79 (d, J = 2.0 Hz, 2H), 3.46 (dd, J = 20.4, 9.3 Hz, 2H), 3.38 (s, 1H), 3.35 - 3.31 (m, 1H), 3.23 (d, J = 9.5 Hz, 1H), 3.11 (d, J = 9.5 Hz, 1H), 2.88 (dd, J = 13.5, 3.0 Hz, 1H), 2.03 (dd, J = 13.5, 10.3 Hz, 1H), 1.93 (d, J = 7.1Hz, 2H), 1.86 - 1.05 (m, 21H), 1.06 - 0.93 (m, 12H), 0.90 - 0.82 (m, 6H), 0.81 (d, J = 11.4 Hz, 1H). LRMS (ESI):647.44 [M+H] + .

[0202] Example 126 (3S,5S,8R,9R,10S,14R,17R,18S)-3-Fluoroacetoxyoleanolic acid-17-(1'S)-(hydroxy)methyl-β-D-mannopyranoside (A126) The remaining raw materials, reagents, and preparation method were the same as in Example 6, but with the exception of 2,3,4,6-O-tetrabenzyl-1-(pyridin-1-yl)sulfonyl-β-D-thioglucopyranoside being replaced with 2,3,4,6-O-tetrabenzyl-1-(pyridin-1-yl)sulfonyl-β-D-thiomannopyranoside, and (3S,5S,8R,9R,10S,14R,17R,18S)-28-O-benzyl-3-aldehyde oleanolic acid being replaced with (5S,8R,9R,10S,14R,17R,18S)-3-fluoroacetoxy-17-aldehyde oleanolic acid. A126 (72% yield) was obtained using the same method as in Example 6. 1H NMR (500 MHz, MeOD) δ 5.28 (s, 1H), 4.16 (s, 1H), 3.79 (d, J = 2.0 Hz, 2H), 3.46 (dd, J = 20.4, 9.3 Hz, 2H), 3.38 (s, 1H), 3.35 - 3.31 (m, 1H), 3.23 (d, J = 9.5 Hz, 1H), 3.11 (d, J = 9.5 Hz, 1H), 2.88 (dd, J = 13.5, 3.0 Hz, 1H), 2.03 (dd, J = 13.5, 10.3 Hz, 1H), 1.93 (d, J = 7.1Hz, 2H), 1.86 - 1.05 (m, 21H), 1.06 - 0.93 (m, 12H), 0.90 - 0.82 (m, 6H), 0.81 (d, J = 11.4 Hz, 1H). LRMS (ESI):665.44 [M+H] + .

[0203] Example 127 (3S,5S,8R,9R,10S,14R,17R,18S)-3-(4-fluorophenylacetoxy)oleanolic acid-17-(1'S)-(hydroxy)methyl-β-D-mannopyranoside (A127) The remaining raw materials, reagents, and preparation method were the same as in Example 6, but A127 (yield 71%) was obtained. 1H NMR (500 MHz, MeOD) δ 5.28 (s, 1H), 4.16 (s, 1H), 3.79 (d, J = 2.0 Hz, 2H), 3.46 (dd, J = 20.4, 9.3 Hz, 2H), 3.38 (s, 1H), 3.35 - 3.31 (m, 1H), 3.23 (d, J = 9.5 Hz, 1H), 3.11 (d, J = 9.5 Hz, 1H), 2.88 (dd, J = 13.5, 3.0 Hz, 1H), 2.03 (dd, J = 13.5, 10.3 Hz, 1H), 1.93 (d, J = 7.1Hz, 2H), 1.86 - 1.05 (m, 21H), 1.06 - 0.93 (m, 12H), 0.90 - 0.82 (m, 6H), 0.81 (d, J = 11.4 Hz, 1H). LRMS (ESI):727.45 [M+H] + .

[0204] Example 128 (3S,5S,8R,9R,10S,14R,17R,18S)-3-(4-trifluoromethylphenylsulfonyloxy)oleanolic acid-17-(1'S)-(hydroxy)methyl-β-D-mannopyranoside (A128) The remaining raw materials, reagents, and preparation method were the same as in Example 6, but A128 (yield 69%) was obtained. 1H NMR (500 MHz, MeOD) δ 5.28 (s, 1H), 4.16 (s, 1H), 3.79 (d, J = 2.0 Hz, 2H), 3.46 (dd, J = 20.4, 9.3 Hz, 2H), 3.38 (s, 1H), 3.35 - 3.31 (m, 1H), 3.23 (d, J = 9.5 Hz, 1H), 3.11 (d, J = 9.5 Hz, 1H), 2.88 (dd, J = 13.5, 3.0 Hz, 1H), 2.03 (dd, J = 13.5, 10.3 Hz, 1H), 1.93 (d, J = 7.1Hz, 2H), 1.86 - 1.05 (m, 21H), 1.06 - 0.93 (m, 12H), 0.90 - 0.82 (m, 6H), 0.81 (d, J = 11.4 Hz, 1H). LRMS (ESI):813.41 [M+H] + .

[0205] Example 129 (3S,5S,8R,9R,10S,14R,17R,18S)-3-(2,3,5,6-tetrafluorophenylbenzamido)oleanolic acid-17-(1'S)-(hydroxy)methyl-β-D-mannopyranoside (A129) The remaining raw materials, reagents, and production method were the same as in Example 6, but A129 (yield 76%) was obtained. 1H NMR (500 MHz, MeOD) δ 5.28 (s, 1H), 4.16 (s, 1H), 3.79 (d, J = 2.0 Hz, 2H), 3.46 (dd, J = 20.4, 9.3 Hz, 2H), 3.38 (s, 1H), 3.35 - 3.31 (m, 1H), 3.23 (d, J = 9.5 Hz, 1H), 3.11 (d, J = 9.5 Hz, 1H), 2.88 (dd, J = 13.5, 3.0 Hz, 1H), 2.03 (dd, J = 13.5, 10.3 Hz, 1H), 1.93 (d, J = 7.1Hz, 2H), 1.86 - 1.05 (m, 21H), 1.06 - 0.93 (m, 12H), 0.90 - 0.82 (m, 6H), 0.81 (d, J = 11.4 Hz, 1H). LRMS (ESI):780.44 [M+H] + .

[0206] Example 130 (3S,5S,8R,9R,10S,14R,17R,18S)-3-(4-trifluoromethylbenzenesulfonamido)oleanolic acid-17-(1'S)-(hydroxy)methyl-β-D-mannopyranoside (A130) The remaining raw materials, reagents, and preparation method were the same as in Example 6, but with the exception of 2,3,4,6-O-tetrabenzyl-1-(pyridin-1-yl)sulfonyl-β-D-thioglucopyranoside, which was replaced with 2,3,4,6-O-tetrabenzyl-1-(pyridin-1-yl)sulfonyl-β-D-thiomannopyranoside, and (3S,5S,8R,9R,10S,14R,17R,18S)-28-O-benzyl-3-aldehyde oleanolic acid, which was replaced with (5S,8R,9R,10S,14R,17R,18S)-3-(4-trifluoromethylbenzenesulfonamido)-17-aldehyde oleanolic acid. A130 (yield 68%) was obtained using the same method as in Example 6. 1H NMR (500 MHz, MeOD) δ 5.28 (s, 1H), 4.16 (s, 1H), 3.79 (d, J = 2.0 Hz, 2H), 3.46 (dd, J = 20.4, 9.3 Hz, 2H), 3.38 (s, 1H), 3.35 - 3.31 (m, 1H), 3.23 (d, J = 9.5 Hz, 1H), 3.11 (d, J = 9.5 Hz, 1H), 2.88 (dd, J = 13.5, 3.0 Hz, 1H), 2.03 (dd, J = 13.5, 10.3 Hz, 1H), 1.93 (d, J = 7.1Hz, 2H), 1.86 - 1.05 (m, 21H), 1.06 - 0.93 (m, 12H), 0.90 - 0.82 (m, 6H), 0.81 (d, J = 11.4 Hz, 1H). LRMS (ESI):812.43 [M+H] + .

[0207] Example 131 (5S,8R,9R,10S,14R,17R,18S)-3-Oximidooleanolic acid-17-(1'S)-(hydroxy)methyl-β-D-mannopyranoside (A131) The remaining raw materials, reagents, and production method were the same as in Example 6, but with the exception of 2,3,4,6-O-tetrabenzyl-1-(pyridin-1-yl)sulfonyl-β-D-thioglucopyranoside being replaced with 2,3,4,6-O-tetrabenzyl-1-(pyridin-1-yl)sulfonyl-β-D-thiomannopyranoside, and (3S,5S,8R,9R,10S,14R,17R,18S)-28-O-benzyl-3-aldehyde oleanolic acid being replaced with (5S,8R,9R,10S,14R,17R,18S)-3-oximido-17-aldehyde oleanolic acid. A131 (yield 69%) was obtained using the same method as in Example 6. 1H NMR (500 MHz, MeOD) δ 5.28 (s, 1H), 4.16 (s, 1H), 3.79 (d, J = 2.0 Hz, 2H), 3.46 (dd, J = 20.4, 9.3 Hz, 2H), 3.38 (s, 1H), 3.35 - 3.31 (m, 1H), 3.23 (d, J = 9.5 Hz, 1H), 3.11 (d, J = 9.5 Hz, 1H), 2.88 (dd, J = 13.5, 3.0 Hz, 1H), 2.03 (dd, J = 13.5, 10.3 Hz, 1H), 1.93 (d, J = 7.1Hz, 2H), 1.86 - 1.05 (m, 21H), 1.06 - 0.93 (m, 12H), 0.90 - 0.82 (m, 6H), 0.81 (d, J = 11.4 Hz, 1H). LRMS (ESI):618.43 [M+H] + .

[0208] Example 132 (5S,8R,9R,10S,14R,17R,18S)-3-methylhydrazonooleanolic acid-17-(1'S)-(hydroxy)methyl-β-D-mannopyranoside (A132) The remaining raw materials, reagents, and preparation method were the same as in Example 6, but with the exception of 2,3,4,6-O-tetrabenzyl-1-(pyridin-1-yl)sulfonyl-β-D-thioglucopyranoside being replaced with 2,3,4,6-O-tetrabenzyl-1-(pyridin-1-yl)sulfonyl-β-D-thiomannopyranoside, and (3S,5S,8R,9R,10S,14R,17R,18S)-28-O-benzyl-3-aldehyde oleanolic acid being replaced with (5S,8R,9R,10S,14R,17R,18S)-3-methylhydrazono-17-aldehyde oleanolic acid. A132 (79% yield) was obtained using the same method as in Example 6. 1H NMR (500 MHz, MeOD) δ 5.28 (s, 1H), 4.16 (s, 1H), 3.79 (d, J = 2.0 Hz, 2H), 3.46 (dd, J = 20.4, 9.3 Hz, 2H), 3.38 (s, 1H), 3.35 - 3.31 (m, 1H), 3.23 (d, J = 9.5 Hz, 1H), 3.11 (d, J = 9.5 Hz, 1H), 2.88 (dd, J = 13.5, 3.0 Hz, 1H), 2.03 (dd, J = 13.5, 10.3 Hz, 1H), 1.93 (d, J = 7.1Hz, 2H), 1.86 - 1.05 (m, 21H), 1.06 - 0.93 (m, 12H), 0.90 - 0.82 (m, 6H), 0.81 (d, J = 11.4 Hz, 1H). LRMS (ESI):631.46 [M+H] + .

[0209] Example 133 (5S,8R,9R,10S,14R,17R,18S)-3-phenylhydrazonooleanolic acid-17-(1'S)-(hydroxy)methyl-β-D-mannopyranoside (A133) The remaining raw materials, reagents, and production method were the same as in Example 6, but A133 (yield 76%) was obtained. 1H NMR (500 MHz, MeOD) δ 5.28 (s, 1H), 4.16 (s, 1H), 3.79 (d, J = 2.0 Hz, 2H), 3.46 (dd, J = 20.4, 9.3 Hz, 2H), 3.38 (s, 1H), 3.35 - 3.31 (m, 1H), 3.23 (d, J = 9.5 Hz, 1H), 3.11 (d, J = 9.5 Hz, 1H), 2.88 (dd, J = 13.5, 3.0 Hz, 1H), 2.03 (dd, J = 13.5, 10.3 Hz, 1H), 1.93 (d, J = 7.1Hz, 2H), 1.86 - 1.05 (m, 21H), 1.06 - 0.93 (m, 12H), 0.90 - 0.82 (m, 6H), 0.81 (d, J = 11.4 Hz, 1H). LRMS (ESI):693.48 [M+H] + .

[0210] Example 134 (3S,5S,8R,9R,10S,14R,17R,18S)-3-(4-fluorophenylureido)oleanolic acid-17-(1'S)-(hydroxy)methyl-β-D-mannopyranoside (A134) The remaining raw materials, reagents, and preparation method were the same as in Example 6, but A134 (yield 68%) was obtained. 1H NMR (500 MHz, MeOD) δ 5.28 (s, 1H), 4.16 (s, 1H), 3.79 (d, J = 2.0 Hz, 2H), 3.46 (dd, J = 20.4, 9.3 Hz, 2H), 3.38 (s, 1H), 3.35 - 3.31 (m, 1H), 3.23 (d, J = 9.5 Hz, 1H), 3.11 (d, J = 9.5 Hz, 1H), 2.88 (dd, J = 13.5, 3.0 Hz, 1H), 2.03 (dd, J = 13.5, 10.3 Hz, 1H), 1.93 (d, J = 7.1Hz, 2H), 1.86 - 1.05 (m, 21H), 1.06 - 0.93 (m, 12H), 0.90 - 0.82 (m, 6H), 0.81 (d, J = 11.4 Hz, 1H). LRMS (ESI):741.48 [M+H] + .

[0211] Example 135 (3S,5S,8R,9R,10S,14R,17R,18S)-3-(4-fluorophenylthioureido)oleanolic acid-17-(1'S)-(hydroxy)methyl-β-D-mannopyranoside (A135) The remaining raw materials, reagents, and production method were the same as in Example 6, but A135 (yield 71%) was obtained. 1H NMR (500 MHz, MeOD) δ 5.28 (s, 1H), 4.16 (s, 1H), 3.79 (d, J = 2.0 Hz, 2H), 3.46 (dd, J = 20.4, 9.3 Hz, 2H), 3.38 (s, 1H), 3.35 - 3.31 (m, 1H), 3.23 (d, J = 9.5 Hz, 1H), 3.11 (d, J = 9.5 Hz, 1H), 2.88 (dd, J = 13.5, 3.0 Hz, 1H), 2.03 (dd, J = 13.5, 10.3 Hz, 1H), 1.93 (d, J = 7.1Hz, 2H), 1.86 - 1.05 (m, 21H), 1.06 - 0.93 (m, 12H), 0.90 - 0.82 (m, 6H), 0.81 (d, J = 11.4 Hz, 1H). LRMS (ESI):757.45 [M+H] + .

[0212] Example 136 (3S,5S,8R,9R,10S,14R,17R,18S)-3-Formyloleanolic acid-17-(1'S)-(hydroxy)methyl-β-D-mannopyranoside (A136) The remaining raw materials, reagents, and production method were the same as in Example 6, but with the exception of 2,3,4,6-O-tetrabenzyl-1-(pyridin-1-yl)sulfonyl-β-D-thioglucopyranoside being replaced with 2,3,4,6-O-tetrabenzyl-1-(pyridin-1-yl)sulfonyl-β-D-thiomannopyranoside, and (3S,5S,8R,9R,10S,14R,17R,18S)-28-O-benzyl-3-aldehyde oleanolic acid being replaced with (5S,8R,9R,10S,14R,17R,18S)-3-formyl-17-aldehyde oleanolic acid. A136 (72% yield) was obtained using the same method as in Example 6, using the same raw materials, reagents, and production method as in Example 6. 1H NMR (500 MHz, MeOD) δ 5.28 (s, 1H), 4.16 (s, 1H), 3.79 (d, J = 2.0 Hz, 2H), 3.46 (dd, J = 20.4, 9.3 Hz, 2H), 3.38 (s, 1H), 3.35 - 3.31 (m, 1H), 3.23 (d, J = 9.5 Hz, 1H), 3.11 (d, J = 9.5 Hz, 1H), 2.88 (dd, J = 13.5, 3.0 Hz, 1H), 2.03 (dd, J = 13.5, 10.3 Hz, 1H), 1.93 (d, J = 7.1Hz, 2H), 1.86 - 1.05 (m, 21H), 1.06 - 0.93 (m, 12H), 0.90 - 0.82 (m, 6H), 0.81 (d, J = 11.4 Hz, 1H). LRMS (ESI):617.43 [M+H] + .

[0213] Example 137 (3S,5S,8R,9R,10S,14R,17R,18S)-3-(3-fluorocyclobutylthio)oleanolic acid-17-(1'S)-(hydroxy)methyl-β-D-mannopyranoside (A137) The remaining raw materials, reagents, and production method were the same as in Example 6, but A137 (yield 73%) was obtained. 1H NMR (500 MHz, MeOD) δ 5.28 (s, 1H), 4.16 (s, 1H), 3.79 (d, J = 2.0 Hz, 2H), 3.46 (dd, J = 20.4, 9.3 Hz, 2H), 3.38 (s, 1H), 3.35 - 3.31 (m, 1H), 3.23 (d, J = 9.5 Hz, 1H), 3.11 (d, J = 9.5 Hz, 1H), 2.88 (dd, J = 13.5, 3.0 Hz, 1H), 2.03 (dd, J = 13.5, 10.3 Hz, 1H), 1.93 (d, J = 7.1Hz, 2H), 1.86 - 1.05 (m, 21H), 1.06 - 0.93 (m, 12H), 0.90 - 0.82 (m, 6H), 0.81 (d, J = 11.4 Hz, 1H). LRMS (ESI):693.45 [M+H] + .

[0214] Example 138 (3S,5S,8R,9R,10S,14R,17R,18S)-3-phenylthiooleanolic acid-17-(1'S)-(hydroxy)methyl-β-D-mannopyranoside (A138) The remaining raw materials, reagents, and production method were the same as in Example 6, but with the exception of 2,3,4,6-O-tetrabenzyl-1-(pyridin-1-yl)sulfonyl-β-D-thioglucopyranoside, which was replaced with 2,3,4,6-O-tetrabenzyl-1-(pyridin-1-yl)sulfonyl-β-D-thiomannopyranoside, and (3S,5S,8R,9R,10S,14R,17R,18S)-28-O-benzyl-3-aldehyde oleanolic acid, which was replaced with (5S,8R,9R,10S,14R,17R,18S)-3-phenylthio-17-aldehyde oleanolic acid. A138 (yield 69%) was obtained using the same method as in Example 6. 1H NMR (500 MHz, MeOD) δ 5.28 (s, 1H), 4.16 (s, 1H), 3.79 (d, J = 2.0 Hz, 2H), 3.46 (dd, J = 20.4, 9.3 Hz, 2H), 3.38 (s, 1H), 3.35 - 3.31 (m, 1H), 3.23 (d, J = 9.5 Hz, 1H), 3.11 (d, J = 9.5 Hz, 1H), 2.88 (dd, J = 13.5, 3.0 Hz, 1H), 2.03 (dd, J = 13.5, 10.3 Hz, 1H), 1.93 (d, J = 7.1Hz, 2H), 1.86 - 1.05 (m, 21H), 1.06 - 0.93 (m, 12H), 0.90 - 0.82 (m, 6H), 0.81 (d, J = 11.4 Hz, 1H). LRMS (ESI):697.44 [M+H] + .

[0215] Example 139 (5S,8R,9R,10S,14R,17R,18S)-3-carbonyloleanolic acid-28-β-D-mannopyranoside (A139) The remaining raw materials, reagents, and production method were the same as in Example 2, but the compound A139 (yield 71%) was obtained. 1H NMR (500 MHz, MeOD) δ 5.28 (s, 1H), 4.16 (s, 1H), 3.79 (d, J = 2.0 Hz, 2H), 3.46 (dd, J = 20.4, 9.3 Hz, 2H), 3.38 (s, 1H), 3.35 - 3.31 (m, 1H), 3.23 (d, J = 9.5 Hz, 1H), 3.11 (d, J = 9.5 Hz, 1H), 2.88 (dd, J = 13.5, 3.0 Hz, 1H), 2.03 (dd, J = 13.5, 10.3 Hz, 1H), 1.93 (d, J = 7.1Hz, 2H), 1.86 - 1.05 (m, 21H), 1.06 - 0.93 (m, 12H), 0.90 - 0.82 (m, 6H), 0.81 (d, J = 11.4 Hz, 1H). LRMS (ESI):601.40 [M+H] + .

[0216] Example 140 (5S,8R,9R,10S,14R,17R,18S)-3-carbonyloleanolic acid-17-(1'S)-fluoromethyl-β-D-mannopyranoside (A140) The remaining raw materials, reagents, and preparation method were the same as in Example 10, except that 2,3,4,6-O-tetrabenzyl-1-(pyridin-1-yl)sulfonyl-β-D-thioglucopyranoside was replaced with 2,3,4,6-O-tetrabenzyl-1-(pyridin-1-yl)sulfonyl-β-D-thiomannopyranoside, (3S,5S,8R,9R,10S,14R,17R,18S)-28-O-benzyl-3-aldehyde oleanolic acid was replaced with (5S,8R,9R,10S,14R,17R,18S)-3-fluoromethyl-17-aldehyde oleanolic acid, and DAST was used instead. A140 (67% yield) was obtained using the same procedure as in Example 10. 1H NMR (500 MHz, MeOD) δ 5.28 (s, 1H), 4.16 (s, 1H), 3.79 (d, J = 2.0 Hz, 2H), 3.46 (dd, J = 20.4, 9.3 Hz, 2H), 3.38 (s, 1H), 3.35 - 3.31 (m, 1H), 3.23 (d, J = 9.5 Hz, 1H), 3.11 (d, J = 9.5 Hz, 1H), 2.88 (dd, J = 13.5, 3.0 Hz, 1H), 2.03 (dd, J = 13.5, 10.3 Hz, 1H), 1.93 (d, J = 7.1Hz, 2H), 1.86 - 1.05 (m, 21H), 1.06 - 0.93 (m, 12H), 0.90 - 0.82 (m, 6H), 0.81 (d, J = 11.4 Hz, 1H). LRMS (ESI):645.41 [M+H] + .

[0217] Example 141 (5S,8R,9R,10S,14R,17R,18S)-3-carbonyloleanolic acid-17-methyl-β-D-mannopyranoside (A141) The remaining raw materials, reagents, and production method were the same as in Example 10, but A141 (yield 80%) was obtained. 1H NMR (500 MHz, MeOD) δ 5.28 (s, 1H), 4.16 (s, 1H), 3.79 (d, J = 2.0 Hz, 2H), 3.46 (dd, J = 20.4, 9.3 Hz, 2H), 3.38 (s, 1H), 3.35 - 3.31 (m, 1H), 3.23 (d, J = 9.5 Hz, 1H), 3.11 (d, J = 9.5 Hz, 1H), 2.88 (dd, J = 13.5, 3.0 Hz, 1H), 2.03 (dd, J = 13.5, 10.3 Hz, 1H), 1.93 (d, J = 7.1Hz, 2H), 1.86 - 1.05 (m, 21H), 1.06 - 0.93 (m, 12H), 0.90 - 0.82 (m, 6H), 0.81 (d, J = 11.4 Hz, 1H). LRMS (ESI):587.42 [M+H] + .

[0218] Example 142 (5S,8R,9R,10S,14R,17R,18S)-3-carbonyloleanolic acid-17-(1'S)-(hydroxy)methyl-2'',3'',4'',6''-O-tetraacetyl-β-D-mannopyranoside (A142) The remaining raw materials, reagents, and production method were the same as in Example 6, but A142 (yield 67%) was obtained. 1H NMR (500 MHz, MeOD) δ 5.28 (s, 1H), 4.16 (s, 1H), 3.79 (d, J = 2.0 Hz, 2H), 3.46 (dd, J = 20.4, 9.3 Hz, 2H), 3.38 (s, 1H), 3.35 - 3.31 (m, 1H), 3.23 (d, J = 9.5 Hz, 1H), 3.11 (d, J = 9.5 Hz, 1H), 2.88 (dd, J = 13.5, 3.0 Hz, 1H), 2.03 (dd, J = 13.5, 10.3 Hz, 1H), 1.93 (d, J = 7.1Hz, 2H), 1.86 - 1.05 (m, 21H), 1.06 - 0.93 (m, 12H), 0.90 - 0.82 (m, 6H), 0.81 (d, J = 11.4 Hz, 1H). LRMS (ESI):771.46 [M+H] + .

[0219] Example 143 (3S,5S,8R,9R,10S,14R,17R,18S)-Oleanolic acid-17-(1'S)-(hydroxy)methyl-2'',3'',4'',6''-O-tetraacetyl-β-D-mannopyranoside (A143) The remaining raw materials, reagents, and production method were the same as in Example 6, but A143 (yield 66%) was obtained. 1H NMR (500 MHz, MeOD) δ 5.28 (s, 1H), 4.16 (s, 1H), 3.79 (d, J = 2.0 Hz, 2H), 3.46 (dd, J = 20.4, 9.3 Hz, 2H), 3.38 (s, 1H), 3.35 - 3.31 (m, 1H), 3.23 (d, J = 9.5 Hz, 1H), 3.11 (d, J = 9.5 Hz, 1H), 2.88 (dd, J = 13.5, 3.0 Hz, 1H), 2.03 (dd, J = 13.5, 10.3 Hz, 1H), 1.93 (d, J = 7.1Hz, 2H), 1.86 - 1.05 (m, 21H), 1.06 - 0.93 (m, 12H), 0.90 - 0.82 (m, 6H), 0.81 (d, J = 11.4 Hz, 1H). LRMS (ESI): 773.48 [M+H] + .

[0220] Example 144 (5S,8R,9R,10S,14R,17R,18S)-3-carbonyloleanolic acid-17-methyl-2'',3'',4'',6''-O-tetraacetyl-β-D-mannopyranoside (A144) The remaining raw materials, reagents, and production method were the same as in Example 10, but A144 (yield 70%) was obtained. 1H NMR (500 MHz, MeOD) δ 5.28 (s, 1H), 4.16 (s, 1H), 3.79 (d, J = 2.0 Hz, 2H), 3.46 (dd, J = 20.4, 9.3 Hz, 2H), 3.38 (s, 1H), 3.35 - 3.31 (m, 1H), 3.23 (d, J = 9.5 Hz, 1H), 3.11 (d, J = 9.5 Hz, 1H), 2.88 (dd, J = 13.5, 3.0 Hz, 1H), 2.03 (dd, J = 13.5, 10.3 Hz, 1H), 1.93 (d, J = 7.1Hz, 2H), 1.86 - 1.05 (m, 21H), 1.06 - 0.93 (m, 12H), 0.90 - 0.82 (m, 6H), 0.81 (d, J = 11.4 Hz, 1H). LRMS (ESI):755.47 [M+H] + .

[0221] Example 145 (5S,8R,9R,10S,14R,17R,18S)-3-carbonyloleanolic acid-17-(2'S)-(hydroxy)ethyl-β-D-mannopyranoside (A145) The remaining raw materials, reagents, and production method were the same as in Example 6, but A145 (yield 68%) was obtained. 1H NMR (500 MHz, MeOD) δ 5.28 (s, 1H), 4.16 (s, 1H), 3.79 (d, J = 2.0 Hz, 2H), 3.46 (dd, J = 20.4, 9.3 Hz, 2H), 3.38 (s, 1H), 3.35 - 3.31 (m, 1H), 3.23 (d, J = 9.5 Hz, 1H), 3.11 (d, J = 9.5 Hz, 1H), 2.88 (dd, J = 13.5, 3.0 Hz, 1H), 2.03 (dd, J = 13.5, 10.3 Hz, 1H), 1.93 (d, J = 7.1Hz, 2H), 1.86 - 1.05 (m, 21H), 1.06 - 0.93 (m, 12H), 0.90 - 0.82 (m, 6H), 0.81 (d, J = 11.4 Hz, 1H). LRMS (ESI):617.43 [M+H] + .

[0222] Example 146 (5S,8R,9R,10S,14R,17R,18S)-3-carbonyloleanolic acid-17-(2'S)-(hydroxy)ethyl-2'',3'',4'',6''-O-tetraacetyl-β-D-mannopyranoside (A146) The remaining raw materials, reagents, and preparation method were the same as in Example 6, but with the exception of 2,3,4,6-O-tetrabenzyl-1-(pyridin-1-yl)sulfonyl-β-D-thioglucopyranoside being replaced with 2,3,4,6-O-tetraacetyl-1-(pyridin-1-yl)sulfonyl-β-D-thiomannopyranoside, and (3S,5S,8R,9R,10S,14R,17R,18S)-28-O-benzyl-3-aldehyde oleanolic acid being replaced with (5S,8R,9R,10S,14R,17R,18S)-3-carbonyl-17-formylmethyl oleanolic acid. A146 (yield 68%) was obtained using the same method as in Example 6. 1H NMR (500 MHz, MeOD) δ 5.28 (s, 1H), 4.16 (s, 1H), 3.79 (d, J = 2.0 Hz, 2H), 3.46 (dd, J = 20.4, 9.3 Hz, 2H), 3.38 (s, 1H), 3.35 - 3.31 (m, 1H), 3.23 (d, J = 9.5 Hz, 1H), 3.11 (d, J = 9.5 Hz, 1H), 2.88 (dd, J = 13.5, 3.0 Hz, 1H), 2.03 (dd, J = 13.5, 10.3 Hz, 1H), 1.93 (d, J = 7.1Hz, 2H), 1.86 - 1.05 (m, 21H), 1.06 - 0.93 (m, 12H), 0.90 - 0.82 (m, 6H), 0.81 (d, J = 11.4 Hz, 1H). LRMS (ESI):685.48 [M+H] + .

[0223] Example 147 (5S,8R,9R,10S,14R,17R,18S)-3-carbonylursolic acid-17-(2'S)-(hydroxy)ethyl-2'',3'',4'',6''-O-tetraacetyl-β-D-mannopyranoside (A147) The remaining raw materials, reagents, and preparation method were the same as in Example 6, but with the exception of 2,3,4,6-O-tetrabenzyl-1-(pyridin-1-yl)sulfonyl-β-D-thioglucopyranoside being replaced with 2,3,4,6-O-tetraacetyl-1-(pyridin-1-yl)sulfonyl-β-D-thiomannopyranoside, and (3S,5S,8R,9R,10S,14R,17R,18S)-28-O-benzyl-3-aldehyde oleanolic acid being replaced with (5S,8R,9R,10S,14R,17R,18S)-3-carbonyl-17-formylmethylursolic acid. A147 (yield 69%) was obtained using the same method as in Example 6. 1H NMR (500 MHz, MeOD) δ 5.28 (s, 1H), 4.16 (s, 1H), 3.79 (d, J = 2.0 Hz, 2H), 3.46 (dd, J = 20.4, 9.3 Hz, 2H), 3.38 (s, 1H), 3.35 - 3.31 (m, 1H), 3.23 (d, J = 9.5 Hz, 1H), 3.11 (d, J = 9.5 Hz, 1H), 2.88 (dd, J = 13.5, 3.0 Hz, 1H), 2.03 (dd, J = 13.5, 10.3 Hz, 1H), 1.93 (d, J = 7.1Hz, 2H), 1.86 - 1.05 (m, 21H), 1.06 - 0.93 (m, 12H), 0.90 - 0.82 (m, 6H), 0.81 (d, J = 11.4 Hz, 1H). LRMS (ESI):685.48 [M+H] + .

[0224] Example 148 (5S,8R,9R,10S,14R,17R,18S)-3-carbonylbetulinic acid-17-(2'S)-(hydroxy)ethyl-2'',3'',4'',6''-O-tetraacetyl-β-D-mannopyranoside (A148) The remaining raw materials, reagents, and preparation method were the same as in Example 6, but with the exception of 2,3,4,6-O-tetrabenzyl-1-(pyridin-1-yl)sulfonyl-β-D-thioglucopyranoside being replaced with 2,3,4,6-O-tetraacetyl-1-(pyridin-1-yl)sulfonyl-β-D-thiomannopyranoside, and (3S,5S,8R,9R,10S,14R,17R,18S)-28-O-benzyl-3-aldehyde oleanolic acid being replaced with (5S,8R,9R,10S,14R,17R,18S)-3-carbonyl-17-formylmethyl betulinic acid. A148 (71% yield) was obtained using the same method as in Example 6. 1H NMR (500 MHz, MeOD) δ 5.28 (s, 1H), 4.16 (s, 1H), 3.79 (d, J = 2.0 Hz, 2H), 3.46 (dd, J = 20.4, 9.3 Hz, 2H), 3.38 (s, 1H), 3.35 - 3.31 (m, 1H), 3.23 (d, J = 9.5 Hz, 1H), 3.11 (d, J = 9.5 Hz, 1H), 2.88 (dd, J = 13.5, 3.0 Hz, 1H), 2.03 (dd, J = 13.5, 10.3 Hz, 1H), 1.93 (d, J = 7.1Hz, 2H), 1.86 - 1.05 (m, 21H), 1.06 - 0.93 (m, 12H), 0.90 - 0.82 (m, 6H), 0.81 (d, J = 11.4 Hz, 1H). LRMS (ESI):685.48 [M+H] + .

[0225] Example 149 (5S,8R,9R,10S,14R,17R,18S)-3-carbonyloleanolic acid-17-(1'R)-(hydroxy)methyl-β-D-xylopyranoside (A149) The remaining raw materials, reagents, and preparation method were the same as in Example 6, but with the exception of 2,3,4,6-O-tetrabenzyl-1-(pyridin-1-yl)sulfonyl-β-D-thioglucopyranoside being replaced with 2,3,4-O-tribenzyl-1-(pyridin-1-yl)sulfonyl-β-D-thioxilopyranoside, and (3S,5S,8R,9R,10S,14R,17R,18S)-28-O-benzyl-3-aldehyde oleanolic acid being replaced with (5S,8R,9R,10S,14R,17R,18S)-3-carbonyl-17-aldehyde oleanolic acid. A149 (71% yield) was obtained using the same method as in Example 6, using the same starting materials, reagents, and preparation method as in Example 6. 1H NMR (500 MHz, MeOD) δ 5.28 (s, 1H), 4.16 (s, 1H), 3.79 (d, J = 2.0 Hz, 2H), 3.46 (dd, J = 20.4, 9.3 Hz, 2H), 3.38 (s, 1H), 3.35 - 3.31 (m, 1H), 3.23 (d, J = 9.5 Hz, 1H), 3.11 (d, J = 9.5 Hz, 1H), 2.88 (dd, J = 13.5, 3.0 Hz, 1H), 2.03 (dd, J = 13.5, 10.3 Hz, 1H), 1.93 (d, J = 7.1Hz, 2H), 1.86 - 1.05 (m, 21H), 1.06 - 0.93 (m, 12H), 0.90 - 0.82 (m, 6H), 0.81 (d, J = 11.4 Hz, 1H). LRMS (ESI):573.41 [M+H] + .

[0226] Example 150 (5S,8R,9R,10S,14R,17R,18S)-3-carbonyloleanolic acid-17-methyl-β-D-xylopyranoside (A150) The remaining raw materials, reagents, and production method were the same as in Example 10, but with the exception of 2,3,4,6-O-tetrabenzyl-1-(pyridin-1-yl)sulfonyl-β-D-thioglucopyranoside being replaced with 2,3,4-O-tribenzyl-1-(pyridin-1-yl)sulfonyl-β-D-thioxilopyranoside, and (3S,5S,8R,9R,10S,14R,17R,18S)-28-O-benzyl-3-aldehyde oleanolic acid being replaced with (5S,8R,9R,10S,14R,17R,18S)-3-carbonyl-17-aldehyde oleanolic acid. A150 (77% yield) was obtained using the same method as in Example 10. 1H NMR (500 MHz, MeOD) δ 5.28 (s, 1H), 4.16 (s, 1H), 3.79 (d, J = 2.0 Hz, 2H), 3.46 (dd, J = 20.4, 9.3 Hz, 2H), 3.38 (s, 1H), 3.35 - 3.31 (m, 1H), 3.23 (d, J = 9.5 Hz, 1H), 3.11 (d, J = 9.5 Hz, 1H), 2.88 (dd, J = 13.5, 3.0 Hz, 1H), 2.03 (dd, J = 13.5, 10.3 Hz, 1H), 1.93 (d, J = 7.1Hz, 2H), 1.86 - 1.05 (m, 21H), 1.06 - 0.93 (m, 12H), 0.90 - 0.82 (m, 6H), 0.81 (d, J = 11.4 Hz, 1H). LRMS (ESI):557.41 [M+H] + .

[0227] Example 151 (3S,5S,8R,9R,10S,14R,17R,18S)-Oleanolic acid-17-(1'R)-(hydroxy)methyl-β-D-xylopyranoside (A151) The remaining raw materials, reagents, and production method were the same as in Example 6, but with the exception of 2,3,4,6-O-tetrabenzyl-1-(pyridin-1-yl)sulfonyl-β-D-thioglucopyranoside being replaced with 2,3,4-O-tribenzyl-1-(pyridin-1-yl)sulfonyl-β-D-thioxilopyranoside, and (3S,5S,8R,9R,10S,14R,17R,18S)-28-O-benzyl-3-aldehyde oleanolic acid being replaced with (5S,8R,9R,10S,14R,17R,18S)-3-hydroxy-17-aldehyde oleanolic acid. A151 (73% yield) was obtained using the same method as in Example 6, using the same starting materials, reagents, and production method as in Example 6. 1H NMR (500 MHz, MeOD) δ 5.28 (s, 1H), 4.16 (s, 1H), 3.79 (d, J = 2.0 Hz, 2H), 3.46 (dd, J = 20.4, 9.3 Hz, 2H), 3.38 (s, 1H), 3.35 - 3.31 (m, 1H), 3.23 (d, J = 9.5 Hz, 1H), 3.11 (d, J = 9.5 Hz, 1H), 2.88 (dd, J = 13.5, 3.0 Hz, 1H), 2.03 (dd, J = 13.5, 10.3 Hz, 1H), 1.93 (d, J = 7.1Hz, 2H), 1.86 - 1.05 (m, 21H), 1.06 - 0.93 (m, 12H), 0.90 - 0.82 (m, 6H), 0.81 (d, J = 11.4 Hz, 1H). LRMS (ESI):575.42 [M+H] + .

[0228] Example 152 (5S,8R,9R,10S,14R,17R,18S)-3-carbonyloleanolic acid-17-(1'R)-(hydroxy)methyl-2'',3'',4''-O-triacetyl-β-D-xylopyranoside (A152) The remaining raw materials, reagents, and preparation method were the same as in Example 6, but with the exception of 2,3,4,6-O-tetrabenzyl-1-(pyridin-1-yl)sulfonyl-β-D-thioglucopyranoside being replaced with 2,3,4-O-triacetyl-1-(pyridin-1-yl)sulfonyl-β-D-thioxilopyranoside, and (3S,5S,8R,9R,10S,14R,17R,18S)-28-O-benzyl-3-aldehyde oleanolic acid being replaced with (5S,8R,9R,10S,14R,17R,18S)-3-carbonyl-17-aldehyde oleanolic acid. A152 (yield 69%) was obtained using the same method as in Example 6. 1H NMR (500 MHz, MeOD) δ 5.28 (s, 1H), 4.16 (s, 1H), 3.79 (d, J = 2.0 Hz, 2H), 3.46 (dd, J = 20.4, 9.3 Hz, 2H), 3.38 (s, 1H), 3.35 - 3.31 (m, 1H), 3.23 (d, J = 9.5 Hz, 1H), 3.11 (d, J = 9.5 Hz, 1H), 2.88 (dd, J = 13.5, 3.0 Hz, 1H), 2.03 (dd, J = 13.5, 10.3 Hz, 1H), 1.93 (d, J = 7.1Hz, 2H), 1.86 - 1.05 (m, 21H), 1.06 - 0.93 (m, 12H), 0.90 - 0.82 (m, 6H), 0.81 (d, J = 11.4 Hz, 1H). LRMS (ESI):698.44 [M+H] + .

[0229] Example 153 (5S,8R,9R,10S,14R,17R,18S)-3-carbonyloleanolic acid-17-methyl-2'',3'',4''-O-triacetyl-β-D-xylopyranoside (A153) The remaining raw materials, reagents, and production method were the same as in Example 10, but with the exception of 2,3,4,6-O-tetrabenzyl-1-(pyridin-1-yl)sulfonyl-β-D-thioglucopyranoside being replaced with 2,3,4-O-triacetyl-1-(pyridin-1-yl)sulfonyl-β-D-thioxilopyranoside, and (3S,5S,8R,9R,10S,14R,17R,18S)-28-O-benzyl-3-aldehyde oleanolic acid being replaced with (5S,8R,9R,10S,14R,17R,18S)-3-carbonyl-17-aldehyde oleanolic acid. A153 (74% yield) was obtained using the same method as in Example 10. 1H NMR (500 MHz, MeOD) δ 5.28 (s, 1H), 4.16 (s, 1H), 3.79 (d, J = 2.0 Hz, 2H), 3.46 (dd, J = 20.4, 9.3 Hz, 2H), 3.38 (s, 1H), 3.35 - 3.31 (m, 1H), 3.23 (d, J = 9.5 Hz, 1H), 3.11 (d, J = 9.5 Hz, 1H), 2.88 (dd, J = 13.5, 3.0 Hz, 1H), 2.03 (dd, J = 13.5, 10.3 Hz, 1H), 1.93 (d, J = 7.1Hz, 2H), 1.86 - 1.05 (m, 21H), 1.06 - 0.93 (m, 12H), 0.90 - 0.82 (m, 6H), 0.81 (d, J = 11.4 Hz, 1H). LRMS (ESI):683.44 [M+H] + .

[0230] Example 154 (5S,8R,9R,10S,14R,17R,18S)-3-carbonyloleanolic acid-17-(2'R)-(hydroxy)ethyl-2'',3'',4''-O-triacetyl-β-D-xylopyranoside (A154) The remaining raw materials, reagents, and preparation method were the same as in Example 6, but with the exception of 2,3,4,6-O-tetrabenzyl-1-(pyridin-1-yl)sulfonyl-β-D-thioglucopyranoside being replaced with 2,3,4-O-triacetyl-1-(pyridin-1-yl)sulfonyl-β-D-thioxilopyranoside, and (3S,5S,8R,9R,10S,14R,17R,18S)-28-O-benzyl-3-aldehyde oleanolic acid being replaced with (5S,8R,9R,10S,14R,17R,18S)-3-carbonyl-17-formylmethyl oleanolic acid. A154 (70% yield) was obtained using the same method as in Example 6, using the same starting materials, reagents, and preparation method as in Example 6. 1H NMR (500 MHz, MeOD) δ 5.28 (s, 1H), 4.16 (s, 1H), 3.79 (d, J = 2.0 Hz, 2H), 3.46 (dd, J = 20.4, 9.3 Hz, 2H), 3.38 (s, 1H), 3.35 - 3.31 (m, 1H), 3.23 (d, J = 9.5 Hz, 1H), 3.11 (d, J = 9.5 Hz, 1H), 2.88 (dd, J = 13.5, 3.0 Hz, 1H), 2.03 (dd, J = 13.5, 10.3 Hz, 1H), 1.93 (d, J = 7.1Hz, 2H), 1.86 - 1.05 (m, 21H), 1.06 - 0.93 (m, 12H), 0.90 - 0.82 (m, 6H), 0.81 (d, J = 11.4 Hz, 1H). LRMS (ESI):713.46 [M+H] + .

[0231] Example 155 (5S,8R,9R,10S,14R,17R,18S)-3-carbonylursolic acid-17-(2'R)-(hydroxy)ethyl-2'',3'',4''-O-triacetyl-β-D-xylopyranoside (A155) The remaining raw materials, reagents, and preparation method were the same as in Example 6, but with the exception of 2,3,4,6-O-tetrabenzyl-1-(pyridin-1-yl)sulfonyl-β-D-thioglucopyranoside being replaced with 2,3,4-O-triacetyl-1-(pyridin-1-yl)sulfonyl-β-D-thioxilopyranoside, and (3S,5S,8R,9R,10S,14R,17R,18S)-28-O-benzyl-3-aldehyde oleanolic acid being replaced with (5S,8R,9R,10S,14R,17R,18S)-3-carbonyl-17-formylmethylursolic acid. A155 (yield 69%) was obtained using the same method as in Example 6. 1H NMR (500 MHz, MeOD) δ 5.28 (s, 1H), 4.16 (s, 1H), 3.79 (d, J = 2.0 Hz, 2H), 3.46 (dd, J = 20.4, 9.3 Hz, 2H), 3.38 (s, 1H), 3.35 - 3.31 (m, 1H), 3.23 (d, J = 9.5 Hz, 1H), 3.11 (d, J = 9.5 Hz, 1H), 2.88 (dd, J = 13.5, 3.0 Hz, 1H), 2.03 (dd, J = 13.5, 10.3 Hz, 1H), 1.93 (d, J = 7.1Hz, 2H), 1.86 - 1.05 (m, 21H), 1.06 - 0.93 (m, 12H), 0.90 - 0.82 (m, 6H), 0.81 (d, J = 11.4 Hz, 1H). LRMS (ESI):713.46 [M+H] + .

[0232] Example 156 (5S,8R,9R,10S,14R,17R,18S)-3-carbonylbetulinic acid-17-(2'R)-(hydroxy)ethyl-2'',3'',4''-O-triacetyl-β-D-xylopyranoside (A156) The remaining raw materials, reagents, and preparation method were the same as in Example 6, but with the exception of 2,3,4,6-O-tetrabenzyl-1-(pyridin-1-yl)sulfonyl-β-D-thioglucopyranoside being replaced with 2,3,4-O-triacetyl-1-(pyridin-1-yl)sulfonyl-β-D-thioxilopyranoside, and (3S,5S,8R,9R,10S,14R,17R,18S)-28-O-benzyl-3-aldehyde oleanolic acid being replaced with (5S,8R,9R,10S,14R,17R,18S)-3-carbonyl-17-formylmethyl betulinic acid. A156 (71% yield) was obtained using the same method as in Example 6. 1H NMR (500 MHz, MeOD) δ 5.28 (s, 1H), 4.16 (s, 1H), 3.79 (d, J = 2.0 Hz, 2H), 3.46 (dd, J = 20.4, 9.3 Hz, 2H), 3.38 (s, 1H), 3.35 - 3.31 (m, 1H), 3.23 (d, J = 9.5 Hz, 1H), 3.11 (d, J = 9.5 Hz, 1H), 2.88 (dd, J = 13.5, 3.0 Hz, 1H), 2.03 (dd, J = 13.5, 10.3 Hz, 1H), 1.93 (d, J = 7.1Hz, 2H), 1.86 - 1.05 (m, 21H), 1.06 - 0.93 (m, 12H), 0.90 - 0.82 (m, 6H), 0.81 (d, J = 11.4 Hz, 1H). LRMS (ESI) :713.46 [M+H] + .

[0233] Example 157 (5S,8R,9R,10S,14R,17R,18S)-3-carbonyloleanolic acid-17-(1'R)-(hydroxy)methyl-β-D-galactopyranoside (A157) The remaining raw materials, reagents, and production method were the same as in Example 6, but with the exception of 2,3,4,6-O-tetrabenzyl-1-(pyridin-1-yl)sulfonyl-β-D-thioglucopyranoside being replaced with 2,3,4,6-O-tetrabenzyl-1-(pyridin-1-yl)sulfonyl-β-D-thiogalactopyranoside, and (3S,5S,8R,9R,10S,14R,17R,18S)-28-O-benzyl-3-aldehyde oleanolic acid being replaced with (5S,8R,9R,10S,14R,17R,18S)-3-carbonyl-17-aldehyde oleanolic acid. A157 (70% yield) was obtained using the same method as in Example 6, using the same raw materials, reagents, and production method as in Example 6. 1H NMR (500 MHz, MeOD) δ 5.28 (s, 1H), 4.16 (s, 1H), 3.79 (d, J = 2.0 Hz, 2H), 3.46 (dd, J = 20.4, 9.3 Hz, 2H), 3.38 (s, 1H), 3.35 - 3.31 (m, 1H), 3.23 (d, J = 9.5 Hz, 1H), 3.11 (d, J = 9.5 Hz, 1H), 2.88 (dd, J = 13.5, 3.0 Hz, 1H), 2.03 (dd, J = 13.5, 10.3 Hz, 1H), 1.93 (d, J = 7.1Hz, 2H), 1.86 - 1.05 (m, 21H), 1.06 - 0.93 (m, 12H), 0.90 - 0.82 (m, 6H), 0.81 (d, J = 11.4 Hz, 1H). LRMS (ESI):603.42 [M+H] + .

[0234] Example 158 (5S,8R,9R,10S,14R,17R,18S)-3-carbonyloleanolic acid-17-methyl-β-D-galactopyranoside (A158) The remaining raw materials, reagents, and preparation method were the same as in Example 10, but with the exception of 2,3,4,6-O-tetrabenzyl-1-(pyridin-1-yl)sulfonyl-β-D-thioglucopyranoside being replaced with 2,3,4,6-O-tetrabenzyl-1-(pyridin-1-yl)sulfonyl-β-D-thiogalactopyranoside, and (3S,5S,8R,9R,10S,14R,17R,18S)-28-O-benzyl-3-aldehyde oleanolic acid being replaced with (5S,8R,9R,10S,14R,17R,18S)-3-carbonyl-17-aldehyde oleanolic acid. A158 (76% yield) was obtained using the same method as in Example 10. 1H NMR (500 MHz, MeOD) δ 5.28 (s, 1H), 4.16 (s, 1H), 3.79 (d, J = 2.0 Hz, 2H), 3.46 (dd, J = 20.4, 9.3 Hz, 2H), 3.38 (s, 1H), 3.35 - 3.31 (m, 1H), 3.23 (d, J = 9.5 Hz, 1H), 3.11 (d, J = 9.5 Hz, 1H), 2.88 (dd, J = 13.5, 3.0 Hz, 1H), 2.03 (dd, J = 13.5, 10.3 Hz, 1H), 1.93 (d, J = 7.1Hz, 2H), 1.86 - 1.05 (m, 21H), 1.06 - 0.93 (m, 12H), 0.90 - 0.82 (m, 6H), 0.81 (d, J = 11.4 Hz, 1H). LRMS (ESI):587.42 [M+H] + .

[0235] Example 159 (3S,5S,8R,9R,10S,14R,17R,18S)-Oleanolic acid-17-(1'R)-(hydroxy)methyl-β-D-galactopyranoside (A159) The remaining raw materials, reagents, and production method were the same as in Example 6, but with the exception of 2,3,4,6-O-tetrabenzyl-1-(pyridin-1-yl)sulfonyl-β-D-thioglucopyranoside being replaced with 2,3,4,6-O-tetrabenzyl-1-(pyridin-1-yl)sulfonyl-β-D-thiogalactopyranoside, and (3S,5S,8R,9R,10S,14R,17R,18S)-28-O-benzyl-3-aldehyde oleanolic acid being replaced with (5S,8R,9R,10S,14R,17R,18S)-3-hydroxy-17-aldehyde oleanolic acid. A159 (74% yield) was obtained using the same method as in Example 6, using the same starting materials, reagents, and production method as in Example 6. 1H NMR (500 MHz, MeOD) δ 5.28 (s, 1H), 4.16 (s, 1H), 3.79 (d, J = 2.0 Hz, 2H), 3.46 (dd, J = 20.4, 9.3 Hz, 2H), 3.38 (s, 1H), 3.35 - 3.31 (m, 1H), 3.23 (d, J = 9.5 Hz, 1H), 3.11 (d, J = 9.5 Hz, 1H), 2.88 (dd, J = 13.5, 3.0 Hz, 1H), 2.03 (dd, J = 13.5, 10.3 Hz, 1H), 1.93 (d, J = 7.1Hz, 2H), 1.86 - 1.05 (m, 21H), 1.06 - 0.93 (m, 1H), 0.90 - 0.82 (m, 6H), 0.81 (d, J = 11.4 Hz, 1H). LRMS (ESI):605.43 [M+H] + .

[0236] Example 160 (5S,8R,9R,10S,14R,17R,18S)-3-carbonyloleanolic acid-17-(1'R)-(hydroxy)methyl-2'',3'',4'',6''-O-tetraacetyl-β-D-galactopyranoside (A160) The remaining raw materials, reagents, and production method were the same as in Example 6, but with the exception of 2,3,4,6-O-tetrabenzyl-1-(pyridin-1-yl)sulfonyl-β-D-thioglucopyranoside being replaced with 2,3,4,6-O-tetraacetyl-1-(pyridin-1-yl)sulfonyl-β-D-thiogalactopyranoside, and (3S,5S,8R,9R,10S,14R,17R,18S)-28-O-benzyl-3-aldehyde oleanolic acid being replaced with (5S,8R,9R,10S,14R,17R,18S)-3-carbonyl-17-aldehyde oleanolic acid. A160 (70% yield) was obtained using the same method as in Example 6, using the same raw materials, reagents, and production method as in Example 6. 1H NMR (500 MHz, MeOD) δ 5.28 (s, 1H), 4.16 (s, 1H), 3.79 (d, J = 2.0 Hz, 2H), 3.46 (dd, J = 20.4, 9.3 Hz, 2H), 3.38 (s, 1H), 3.35 - 3.31 (m, 1H), 3.23 (d, J = 9.5 Hz, 1H), 3.11 (d, J = 9.5 Hz, 1H), 2.88 (dd, J = 13.5, 3.0 Hz, 1H), 2.03 (dd, J = 13.5, 10.3 Hz, 1H), 1.93 (d, J = 7.1Hz, 2H), 1.86 - 1.05 (m, 21H), 1.06 - 0.93 (m, 12H), 0.90 - 0.82 (m, 6H), 0.81 (d, J = 11.4 Hz, 1H). LRMS (ESI):771.46 [M+H] + .

[0237] Example 161 (5S,8R,9R,10S,14R,17R,18S)-3-carbonyloleanolic acid-17-methyl-2'',3'',4'',6''-O-tetraacetyl-β-D-galactopyranoside (A161) The remaining raw materials, reagents, and preparation method were the same as in Example 10, but with the exception of 2,3,4,6-O-tetrabenzyl-1-(pyridin-1-yl)sulfonyl-β-D-thioglucopyranoside being replaced with 2,3,4,6-O-tetraacetyl-1-(pyridin-1-yl)sulfonyl-β-D-thiogalactopyranoside, and (3S,5S,8R,9R,10S,14R,17R,18S)-28-O-benzyl-3-aldehyde oleanolic acid being replaced with (5S,8R,9R,10S,14R,17R,18S)-3-carbonyl-17-aldehyde oleanolic acid. A161 (74% yield) was obtained using the same method as in Example 10. 1H NMR (500 MHz, MeOD) δ 5.28 (s, 1H), 4.16 (s, 1H), 3.79 (d, J = 2.0 Hz, 2H), 3.46 (dd, J = 20.4, 9.3 Hz, 2H), 3.38 (s, 1H), 3.35 - 3.31 (m, 1H), 3.23 (d, J = 9.5 Hz, 1H), 3.11 (d, J = 9.5 Hz, 1H), 2.88 (dd, J = 13.5, 3.0 Hz, 1H), 2.03 (dd, J = 13.5, 10.3 Hz, 1H), 1.93 (d, J = 7.1Hz, 2H), 1.86 - 1.05 (m, 21H), 1.06 - 0.93 (m, 12H), 0.90 - 0.82 (m, 6H), 0.81 (d, J = 11.4 Hz, 1H). LRMS (ESI):755.47 [M+H] + .

[0238] Example 162 (5S,8R,9R,10S,14R,17R,18S)-3-carbonyloleanolic acid-17-(2'R)-(hydroxy)ethyl-β-D-galactopyranoside (A162) The remaining raw materials, reagents, and preparation method were the same as in Example 6, but with the exception of 2,3,4,6-O-tetrabenzyl-1-(pyridin-1-yl)sulfonyl-β-D-thioglucopyranoside being replaced with 2,3,4,6-O-tetrabenzyl-1-(pyridin-1-yl)sulfonyl-β-D-thiogalactopyranoside, and (3S,5S,8R,9R,10S,14R,17R,18S)-28-O-benzyl-3-aldehyde oleanolic acid being replaced with (5S,8R,9R,10S,14R,17R,18S)-3-carbonyl-17-formylmethyl oleanolic acid. A162 (yield 68%) was obtained using the same method as in Example 6. 1H NMR (500 MHz, MeOD) δ 5.28 (s, 1H), 4.16 (s, 1H), 3.79 (d, J = 2.0 Hz, 2H), 3.46 (dd, J = 20.4, 9.3 Hz, 2H), 3.38 (s, 1H), 3.35 - 3.31 (m, 1H), 3.23 (d, J = 9.5 Hz, 1H), 3.11 (d, J = 9.5 Hz, 1H), 2.88 (dd, J = 13.5, 3.0 Hz, 1H), 2.03 (dd, J = 13.5, 10.3 Hz, 1H), 1.93 (d, J = 7.1Hz, 2H), 1.86 - 1.05 (m, 21H), 1.06 - 0.93 (m, 12H), 0.90 - 0.82 (m, 6H), 0.81 (d, J = 11.4 Hz, 1H). LRMS (ESI):617.43 [M+H] + .

[0239] Example 163 (5S,8R,9R,10S,14R,17R,18S)-3-carbonyloleanolic acid-17-(2'R)-(hydroxy)ethyl-2'',3'',4'',6''-O-tetraacetyl-β-D-galactopyranoside (A163) The remaining raw materials, reagents, and preparation method were the same as in Example 6, but with the exception of 2,3,4,6-O-tetrabenzyl-1-(pyridin-1-yl)sulfonyl-β-D-thioglucopyranoside being replaced with 2,3,4,6-O-tetraacetyl-1-(pyridin-1-yl)sulfonyl-β-D-thiogalactopyranoside, and (3S,5S,8R,9R,10S,14R,17R,18S)-28-O-benzyl-3-aldehyde oleanolic acid being replaced with (5S,8R,9R,10S,14R,17R,18S)-3-carbonyl-17-formylmethyl oleanolic acid. A163 (72% yield) was obtained using the same method as in Example 6, using the same raw materials, reagents, and preparation method as in Example 6. 1H NMR (500 MHz, MeOD) δ 5.28 (s, 1H), 4.16 (s, 1H), 3.79 (d, J = 2.0 Hz, 2H), 3.46 (dd, J = 20.4, 9.3 Hz, 2H), 3.38 (s, 1H), 3.35 - 3.31 (m, 1H), 3.23 (d, J = 9.5 Hz, 1H), 3.11 (d, J = 9.5 Hz, 1H), 2.88 (dd, J = 13.5, 3.0 Hz, 1H), 2.03 (dd, J = 13.5, 10.3 Hz, 1H), 1.93 (d, J = 7.1Hz, 2H), 1.86 - 1.05 (m, 21H), 1.06 - 0.93 (m, 12H), 0.90 - 0.82 (m, 6H), 0.81 (d, J = 11.4 Hz, 1H). LRMS (ESI):785.48 [M+H] + .

[0240] Example 164 (5S,8R,9R,10S,14R,17R,18S)-3-carbonylursolic acid-17-(2'R)-(hydroxy)ethyl-2'',3'',4'',6''-O-tetraacetyl-β-D-galactopyranoside (A164) The remaining raw materials, reagents, and preparation method were the same as in Example 6, but with the exception of 2,3,4,6-O-tetrabenzyl-1-(pyridin-1-yl)sulfonyl-β-D-thioglucopyranoside being replaced with 2,3,4,6-O-tetraacetyl-1-(pyridin-1-yl)sulfonyl-β-D-thiogalactopyranoside, and (3S,5S,8R,9R,10S,14R,17R,18S)-28-O-benzyl-3-aldehyde oleanolic acid being replaced with (5S,8R,9R,10S,14R,17R,18S)-3-carbonyl-17-formylmethylursolic acid. A164 (68% yield) was obtained using the same method as in Example 6. 1H NMR (500 MHz, MeOD) δ 5.28 (s, 1H), 4.16 (s, 1H), 3.79 (d, J = 2.0 Hz, 2H), 3.46 (dd, J = 20.4, 9.3 Hz, 2H), 3.38 (s, 1H), 3.35 - 3.31 (m, 1H), 3.23 (d, J = 9.5 Hz, 1H), 3.11 (d, J = 9.5 Hz, 1H), 2.88 (dd, J = 13.5, 3.0 Hz, 1H), 2.03 (dd, J = 13.5, 10.3 Hz, 1H), 1.93 (d, J = 7.1Hz, 2H), 1.86 - 1.05 (m, 21H), 1.06 - 0.93 (m, 12H), 0.90 - 0.82 (m, 6H), 0.81 (d, J = 11.4 Hz, 1H). LRMS (ESI): 785.48 [M+H] + .

[0241] Example 165 (5S,8R,9R,10S,14R,17R,18S)-3-carbonylbetulinic acid-17-(2'R)-(hydroxy)ethyl-2'',3'',4'',6''-O-tetraacetyl-β-D-galactopyranoside (A165) The remaining raw materials, reagents, and preparation method were the same as in Example 6, but with the exception of 2,3,4,6-O-tetrabenzyl-1-(pyridin-1-yl)sulfonyl-β-D-thioglucopyranoside being replaced with 2,3,4,6-O-tetraacetyl-1-(pyridin-1-yl)sulfonyl-β-D-thiogalactopyranoside, and (3S,5S,8R,9R,10S,14R,17R,18S)-28-O-benzyl-3-aldehyde oleanolic acid being replaced with (5S,8R,9R,10S,14R,17R,18S)-3-carbonyl-17-formylmethyl betulinic acid. A165 (74% yield) was obtained using the same method as in Example 6. 1H NMR (500 MHz, MeOD) δ 5.28 (s, 1H), 4.16 (s, 1H), 3.79 (d, J = 2.0 Hz, 2H), 3.46 (dd, J = 20.4, 9.3 Hz, 2H), 3.38 (s, 1H), 3.35 - 3.31 (m, 1H), 3.23 (d, J = 9.5 Hz, 1H), 3.11 (d, J = 9.5 Hz, 1H), 2.88 (dd, J = 13.5, 3.0 Hz, 1H), 2.03 (dd, J = 13.5, 10.3 Hz, 1H), 1.93 (d, J = 7.1Hz, 2H), 1.86 - 1.05 (m, 21H), 1.06 - 0.93 (m, 12H), 0.90 - 0.82 (m, 6H), 0.81 (d, J = 11.4 Hz, 1H). LRMS (ESI) : 785.48 [M+H] + .

[0242] Example 166 (5S,8R,9R,10S,14R,17R,18S)-3-carbonyloleanolic acid-17-(1'R)-(hydroxy)methyl-α-L-rhamnopyranoside (A166) The remaining raw materials, reagents, and preparation method were the same as in Example 6, but with the exception of 2,3,4,6-O-tetrabenzyl-1-(pyridin-1-yl)sulfonyl-β-D-thioglucopyranoside being replaced with 2,3,4-O-tribenzyl-1-(pyridin-1-yl)sulfonyl-β-D-thiorhamnopyranoside, and (3S,5S,8R,9R,10S,14R,17R,18S)-28-O-benzyl-3-aldehyde oleanolic acid being replaced with (5S,8R,9R,10S,14R,17R,18S)-3-carbonyl-17-aldehyde oleanolic acid. A166 (74% yield) was obtained using the same method as in Example 6. 1H NMR (500 MHz, MeOD) δ 5.28 (s, 1H), 4.16 (s, 1H), 3.79 (d, J = 2.0 Hz, 2H), 3.46 (dd, J = 20.4, 9.3 Hz, 2H), 3.38 (s, 1H), 3.35 - 3.31 (m, 1H), 3.23 (d, J = 9.5 Hz, 1H), 3.11 (d, J = 9.5 Hz, 1H), 2.88 (dd, J = 13.5, 3.0 Hz, 1H), 2.03 (dd, J = 13.5, 10.3 Hz, 1H), 1.93 (d, J = 7.1Hz, 2H), 1.86 - 1.05 (m, 21H), 1.06 - 0.93 (m, 12H), 0.90 - 0.82 (m, 6H), 0.81 (d, J = 11.4 Hz, 1H). LRMS (ESI):587.42 [M+H] + .

[0243] Example 167 (5S,8R,9R,10S,14R,17R,18S)-3-carbonyloleanolic acid-17-methyl-α-L-rhamnopyranoside (A167) The remaining raw materials, reagents, and production method were the same as in Example 10, but the compound A167 (yield 74%) was obtained. 1H NMR (500 MHz, MeOD) δ 5.28 (s, 1H), 4.16 (s, 1H), 3.79 (d, J = 2.0 Hz, 2H), 3.46 (dd, J = 20.4, 9.3 Hz, 2H), 3.38 (s, 1H), 3.35 - 3.31 (m, 1H), 3.23 (d, J = 9.5 Hz, 1H), 3.11 (d, J = 9.5 Hz, 1H), 2.88 (dd, J = 13.5, 3.0 Hz, 1H), 2.03 (dd, J = 13.5, 10.3 Hz, 1H), 1.93 (d, J = 7.1Hz, 2H), 1.86 - 1.05 (m, 21H), 1.06 - 0.93 (m, 12H), 0.90 - 0.82 (m, 6H), 0.81 (d, J = 11.4 Hz, 1H). LRMS (ESI):571.43 [M+H] + .

[0244] Example 168 (3S,5S,8R,9R,10S,14R,17R,18S)-Oleanolic acid-17-(1'R)-(hydroxy)methyl-α-L-rhamnopyranoside (A168) The remaining raw materials, reagents, and production method were the same as in Example 6, but with the exception of 2,3,4,6-O-tetrabenzyl-1-(pyridin-1-yl)sulfonyl-β-D-thioglucopyranoside being replaced with 2,3,4-O-tribenzyl-1-(pyridin-1-yl)sulfonyl-β-D-thiorhamnopyranoside, and (3S,5S,8R,9R,10S,14R,17R,18S)-28-O-benzyl-3-aldehyde oleanolic acid being replaced with (5S,8R,9R,10S,14R,17R,18S)-3-hydroxy-17-aldehyde oleanolic acid. A168 (75% yield) was obtained using the same method as in Example 6, using the same starting materials, reagents, and production method as in Example 6. 1H NMR (500 MHz, MeOD) δ 5.28 (s, 1H), 4.16 (s, 1H), 3.79 (d, J = 2.0 Hz, 2H), 3.46 (dd, J = 20.4, 9.3 Hz, 2H), 3.38 (s, 1H), 3.35 - 3.31 (m, 1H), 3.23 (d, J = 9.5 Hz, 1H), 3.11 (d, J = 9.5 Hz, 1H), 2.88 (dd, J = 13.5, 3.0 Hz, 1H), 2.03 (dd, J = 13.5, 10.3 Hz, 1H), 1.93 (d, J = 7.1Hz, 2H), 1.86 - 1.05 (m, 21H), 1.06 - 0.93 (m, 1H), 0.90 - 0.82 (m, 6H), 0.81 (d, J = 11.4 Hz, 1H). LRMS (ESI):589.44 [M+H] + .

[0245] Example 169 (5S,8R,9R,10S,14R,17R,18S)-3-carbonyloleanolic acid-17-(1'R)-(hydroxy)methyl-2'',3'',4''-O-triacetyl-α-L-rhamnopyranoside (A169) The remaining raw materials, reagents, and production method were the same as in Example 6, but with the exception of 2,3,4,6-O-tetrabenzyl-1-(pyridin-1-yl)sulfonyl-β-D-thioglucopyranoside being replaced with 2,3,4-O-triacetyl-1-(pyridin-1-yl)sulfonyl-β-D-thiorhamnopyranoside, and (3S,5S,8R,9R,10S,14R,17R,18S)-28-O-benzyl-3-aldehyde oleanolic acid being replaced with (5S,8R,9R,10S,14R,17R,18S)-3-carbonyl-17-aldehyde oleanolic acid. A169 (73% yield) was obtained using the same method as in Example 6. 1H NMR (500 MHz, MeOD) δ 5.28 (s, 1H), 4.16 (s, 1H), 3.79 (d, J = 2.0 Hz, 2H), 3.46 (dd, J = 20.4, 9.3 Hz, 2H), 3.38 (s, 1H), 3.35 - 3.31 (m, 1H), 3.23 (d, J = 9.5 Hz, 1H), 3.11 (d, J = 9.5 Hz, 1H), 2.88 (dd, J = 13.5, 3.0 Hz, 1H), 2.03 (dd, J = 13.5, 10.3 Hz, 1H), 1.93 (d, J = 7.1Hz, 2H), 1.86 - 1.05 (m, 21H), 1.06 - 0.93 (m, 12H), 0.90 - 0.82 (m, 6H), 0.81 (d, J = 11.4 Hz, 1H). LRMS (ESI):713.46 [M+H] + .

[0246] Example 170 (5S,8R,9R,10S,14R,17R,18S)-3-carbonyloleanolic acid-17-methyl-2'',3'',4''-O-triacetyl-α-L-rhamnopyranoside (A170) The remaining raw materials, reagents, and preparation method were the same as in Example 10, except that 2,3,4,6-O-tetrabenzyl-1-(pyridin-1-yl)sulfonyl-β-D-thioglucopyranoside was replaced with 2,3,4-O-triacetyl-1-(pyridin-1-yl)sulfonyl-β-D-thiorhamnopyranoside, and (3S,5S,8R,9R,10S,14R,17R,18S)-28-O-benzyl-3-aldehyde oleanolic acid was replaced with (5S,8R,9R,10S,14R,17R,18S)-3-carbonyl-17-aldehyde oleanolic acid. A170 (74% yield) was obtained using the same method as in Example 10. 1H NMR (500 MHz, MeOD) δ 5.28 (s, 1H), 4.16 (s, 1H), 3.79 (d, J = 2.0 Hz, 2H), 3.46 (dd, J = 20.4, 9.3 Hz, 2H), 3.38 (s, 1H), 3.35 - 3.31 (m, 1H), 3.23 (d, J = 9.5 Hz, 1H), 3.11 (d, J = 9.5 Hz, 1H), 2.88 (dd, J = 13.5, 3.0 Hz, 1H), 2.03 (dd, J = 13.5, 10.3 Hz, 1H), 1.93 (d, J = 7.1Hz, 2H), 1.86 - 1.05 (m, 21H), 1.06 - 0.93 (m, 12H), 0.90 - 0.82 (m, 6H), 0.81 (d, J = 11.4 Hz, 1H). LRMS (ESI):697.46 [M+H] + .

[0247] Example 171 (5S,8R,9R,10S,14R,17R,18S)-3-carbonyloleanolic acid-17-(2'R)-(hydroxy)ethyl-α-L-rhamnopyranoside (A171) The remaining raw materials, reagents, and preparation method were the same as in Example 6, but with the exception of 2,3,4,6-O-tetrabenzyl-1-(pyridin-1-yl)sulfonyl-β-D-thioglucopyranoside being replaced with 2,3,4-O-tribenzyl-1-(pyridin-1-yl)sulfonyl-β-D-thiorhamnopyranoside, and (3S,5S,8R,9R,10S,14R,17R,18S)-28-O-benzyl-3-aldehyde oleanolic acid being replaced with (5S,8R,9R,10S,14R,17R,18S)-3-carbonyl-17-formylmethyl oleanolic acid. A171 (70% yield) was obtained using the same method as in Example 6, using the same starting materials, reagents, and preparation method as in Example 6. 1H NMR (500 MHz, MeOD) δ 5.28 (s, 1H), 4.16 (s, 1H), 3.79 (d, J = 2.0 Hz, 2H), 3.46 (dd, J = 20.4, 9.3 Hz, 2H), 3.38 (s, 1H), 3.35 - 3.31 (m, 1H), 3.23 (d, J = 9.5 Hz, 1H), 3.11 (d, J = 9.5 Hz, 1H), 2.88 (dd, J = 13.5, 3.0 Hz, 1H), 2.03 (dd, J = 13.5, 10.3 Hz, 1H), 1.93 (d, J = 7.1Hz, 2H), 1.86 - 1.05 (m, 21H), 1.06 - 0.93 (m, 12H), 0.90 - 0.82 (m, 6H), 0.81 (d, J = 11.4 Hz, 1H). LRMS (ESI):601.44 [M+H] + .

[0248] Example 172 (5S,8R,9R,10S,14R,17R,18S)-3-carbonyloleanolic acid-17-(2'R)-(hydroxy)ethyl-2'',3'',4''-O-triacetyl-α-L-rhamnopyranoside (A172) The remaining raw materials, reagents, and preparation method were the same as in Example 6, but with the exception of 2,3,4,6-O-tetrabenzyl-1-(pyridin-1-yl)sulfonyl-β-D-thioglucopyranoside being replaced with 2,3,4-O-triacetyl-1-(pyridin-1-yl)sulfonyl-β-D-thiorhamnopyranoside, and (3S,5S,8R,9R,10S,14R,17R,18S)-28-O-benzyl-3-aldehyde oleanolic acid being replaced with (5S,8R,9R,10S,14R,17R,18S)-3-carbonyl-17-formylmethyl oleanolic acid. A172 (72% yield) was obtained using the same method as in Example 6, using the same starting materials, reagents, and preparation method as in Example 6. 1H NMR (500 MHz, MeOD) δ 5.28 (s, 1H), 4.16 (s, 1H), 3.79 (d, J = 2.0 Hz, 2H), 3.46 (dd, J = 20.4, 9.3 Hz, 2H), 3.38 (s, 1H), 3.35 - 3.31 (m, 1H), 3.23 (d, J = 9.5 Hz, 1H), 3.11 (d, J = 9.5 Hz, 1H), 2.88 (dd, J = 13.5, 3.0 Hz, 1H), 2.03 (dd, J = 13.5, 10.3 Hz, 1H), 1.93 (d, J = 7.1Hz, 2H), 1.86 - 1.05 (m, 21H), 1.06 - 0.93 (m, 12H), 0.90 - 0.82 (m, 6H), 0.81 (d, J = 11.4 Hz, 1H). LRMS (ESI):727.47 [M+H] + .

[0249] Example 173 (5S,8R,9R,10S,14R,17R,18S)-3-carbonylursolic acid-17-(2'R)-(hydroxy)ethyl-2'',3'',4''-O-triacetyl-α-L-rhamnopyranoside (A173) The remaining raw materials, reagents, and preparation method were the same as in Example 6, but with the exception of 2,3,4,6-O-tetrabenzyl-1-(pyridin-1-yl)sulfonyl-β-D-thioglucopyranoside being replaced with 2,3,4-O-triacetyl-1-(pyridin-1-yl)sulfonyl-β-D-thiorhamnopyranoside, and (3S,5S,8R,9R,10S,14R,17R,18S)-28-O-benzyl-3-aldehyde oleanolic acid being replaced with (5S,8R,9R,10S,14R,17R,18S)-3-carbonyl-17-formylmethylursolic acid. A173 (yield 69%) was obtained using the same method as in Example 6. 1H NMR (500 MHz, MeOD) δ 5.28 (s, 1H), 4.16 (s, 1H), 3.79 (d, J = 2.0 Hz, 2H), 3.46 (dd, J = 20.4, 9.3 Hz, 2H), 3.38 (s, 1H), 3.35 - 3.31 (m, 1H), 3.23 (d, J = 9.5 Hz, 1H), 3.11 (d, J = 9.5 Hz, 1H), 2.88 (dd, J = 13.5, 3.0 Hz, 1H), 2.03 (dd, J = 13.5, 10.3 Hz, 1H), 1.93 (d, J = 7.1Hz, 2H), 1.86 - 1.05 (m, 21H), 1.06 - 0.93 (m, 12H), 0.90 - 0.82 (m, 6H), 0.81 (d, J = 11.4 Hz, 1H). LRMS (ESI): 727.47 [M+H] + .

[0250] Example 174 (5S,8R,9R,10S,14R,17R,18S)-3-carbonylbetulinic acid-17-(2'R)-(hydroxy)ethyl-2'',3'',4''-O-triacetyl-α-L-rhamnopyranoside (A174) The remaining raw materials, reagents, and preparation method were the same as in Example 6, but with the exception of 2,3,4,6-O-tetrabenzyl-1-(pyridin-1-yl)sulfonyl-β-D-thioglucopyranoside being replaced with 2,3,4-O-triacetyl-1-(pyridin-1-yl)sulfonyl-β-D-thiorhamnopyranoside, and (3S,5S,8R,9R,10S,14R,17R,18S)-28-O-benzyl-3-aldehyde oleanolic acid being replaced with (5S,8R,9R,10S,14R,17R,18S)-3-carbonyl-17-formylmethyl betulinic acid. A174 (71% yield) was obtained using the same method as in Example 6. 1H NMR (500 MHz, MeOD) δ 5.28 (s, 1H), 4.16 (s, 1H), 3.79 (d, J = 2.0 Hz, 2H), 3.46 (dd, J = 20.4, 9.3 Hz, 2H), 3.38 (s, 1H), 3.35 - 3.31 (m, 1H), 3.23 (d, J = 9.5 Hz, 1H), 3.11 (d, J = 9.5 Hz, 1H), 2.88 (dd, J = 13.5, 3.0 Hz, 1H), 2.03 (dd, J = 13.5, 10.3 Hz, 1H), 1.93 (d, J = 7.1Hz, 2H), 1.86 - 1.05 (m, 21H), 1.06 - 0.93 (m, 12H), 0.90 - 0.82 (m, 6H), 0.81 (d, J = 11.4 Hz, 1H). LRMS (ESI) : 727.47 [M+H] + .

[0251] Example 175 (3S,5S,8R,9R,10S,14R,17R,18S)-Oleanolic acid-17-(1'R)-(hydroxy)methyl-β-D-glucuronopyranoside (A175) The remaining raw materials, reagents, and production method were the same as in Example 6, but with the exception of 2,3,4,6-O-tetrabenzyl-1-(pyridin-1-yl)sulfonyl-β-D-thioglucopyranoside being replaced with 2,3,4-O-tribenzyl-1-(pyridin-1-yl)sulfonyl-β-D-thioglucuronopyranoside, and (3S,5S,8R,9R,10S,14R,17R,18S)-28-O-benzyl-3-aldehyde oleanolic acid being replaced with (5S,8R,9R,10S,14R,17R,18S)-3-hydroxy-17-aldehyde oleanolic acid. A175 (70% yield) was obtained using the same method as in Example 6, using the same raw materials, reagents, and production method as in Example 6. 1H NMR (500 MHz, MeOD) δ 5.28 (s, 1H), 4.16 (s, 1H), 3.79 (d, J = 2.0 Hz, 2H), 3.46 (dd, J = 20.4, 9.3 Hz, 2H), 3.38 (s, 1H), 3.35 - 3.31 (m, 1H), 3.23 (d, J = 9.5 Hz, 1H), 3.11 (d, J = 9.5 Hz, 1H), 2.88 (dd, J = 13.5, 3.0 Hz, 1H), 2.03 (dd, J = 13.5, 10.3 Hz, 1H), 1.93 (d, J = 7.1Hz, 2H), 1.86 - 1.05 (m, 21H), 1.06 - 0.93 (m, 1H), 0.90 - 0.82 (m, 6H), 0.81 (d, J = 11.4 Hz, 1H). LRMS (ESI):619.41 [M+H] + .

[0252] Example 176 (5S,8R,9R,10S,14R,17R,18S)-3-carbonyloleanolic acid-17-carbonyl-2'',3'',4''-O-triacetyl-β-D-glucuronopyranoside (A176) The remaining raw materials, reagents, and preparation method were the same as in Example 10, but with the exception of 2,3,4,6-O-tetrabenzyl-1-(pyridin-1-yl)sulfonyl-β-D-thioglucopyranoside being replaced with 2,3,4-O-triacetyl-1-(pyridin-1-yl)sulfonyl-β-D-thioglucuronopyranoside, and (3S,5S,8R,9R,10S,14R,17R,18S)-28-O-benzyl-3-aldehyde oleanolic acid being replaced with (5S,8R,9R,10S,14R,17R,18S)-3-carbonyl-17-aldehyde oleanolic acid. A176 (70% yield) was obtained using the same method as in Example 10. 1H NMR (500 MHz, MeOD) δ 5.28 (s, 1H), 4.16 (s, 1H), 3.79 (d, J = 2.0 Hz, 2H), 3.46 (dd, J = 20.4, 9.3 Hz, 2H), 3.38 (s, 1H), 3.35 - 3.31 (m, 1H), 3.23 (d, J = 9.5 Hz, 1H), 3.11 (d, J = 9.5 Hz, 1H), 2.88 (dd, J = 13.5, 3.0 Hz, 1H), 2.03 (dd, J = 13.5, 10.3 Hz, 1H), 1.93 (d, J = 7.1Hz, 2H), 1.86 - 1.05 (m, 21H), 1.06 - 0.93 (m, 1H), 0.90 - 0.82 (m, 6H), 0.81 (d, J = 11.4 Hz, 1H). LRMS (ESI):741.41 [M+H] + .

[0253] Example 177 (5S,8R,9R,10S,14R,17R,18S)-3-carbonyloleanolic acid-17-(1'R)-(hydroxy)methyl-2'',3'',4''-O-triacetyl-β-D-glucuronopyranoside (A177) The remaining raw materials, reagents, and production method were the same as in Example 6, but with the exception of 2,3,4,6-O-tetrabenzyl-1-(pyridin-1-yl)sulfonyl-β-D-thioglucopyranoside being replaced with 2,3,4-O-triacetyl-1-(pyridin-1-yl)sulfonyl-β-D-thioglucuronopyranoside, and (3S,5S,8R,9R,10S,14R,17R,18S)-28-O-benzyl-3-aldehyde oleanolic acid being replaced with (5S,8R,9R,10S,14R,17R,18S)-3-carbonyl-17-aldehyde oleanolic acid. A177 (71% yield) was obtained using the same method as in Example 6, using the same raw materials, reagents, and production method as in Example 6. 1H NMR (500 MHz, MeOD) δ 5.28 (s, 1H), 4.16 (s, 1H), 3.79 (d, J = 2.0 Hz, 2H), 3.46 (dd, J = 20.4, 9.3 Hz, 2H), 3.38 (s, 1H), 3.35 - 3.31 (m, 1H), 3.23 (d, J = 9.5 Hz, 1H), 3.11 (d, J = 9.5 Hz, 1H), 2.88 (dd, J = 13.5, 3.0 Hz, 1H), 2.03 (dd, J = 13.5, 10.3 Hz, 1H), 1.93 (d, J = 7.1Hz, 2H), 1.86 - 1.05 (m, 21H), 1.06 - 0.93 (m, 12H), 0.90 - 0.82 (m, 6H), 0.81 (d, J = 11.4 Hz, 1H). LRMS (ESI):743.43 [M+H] + .

[0254] Example 178 (5S,8R,9R,10S,14R,17R,18S)-3-carbonyloleanolic acid-17-methyl-2'',3'',4''-O-triacetyl-β-D-glucuronopyranoside (A178) The remaining raw materials, reagents, and preparation method were the same as in Example 10, but with the exception of 2,3,4,6-O-tetrabenzyl-1-(pyridin-1-yl)sulfonyl-β-D-thioglucopyranoside being replaced with 2,3,4-O-triacetyl-1-(pyridin-1-yl)sulfonyl-β-D-thioglucuronopyranoside, and (3S,5S,8R,9R,10S,14R,17R,18S)-28-O-benzyl-3-aldehyde oleanolic acid being replaced with (5S,8R,9R,10S,14R,17R,18S)-3-carbonyl-17-aldehyde oleanolic acid. A178 (yield 69%) was obtained using the same method as in Example 10. 1H NMR (500 MHz, MeOD) δ 5.28 (s, 1H), 4.16 (s, 1H), 3.79 (d, J = 2.0 Hz, 2H), 3.46 (dd, J = 20.4, 9.3 Hz, 2H), 3.38 (s, 1H), 3.35 - 3.31 (m, 1H), 3.23 (d, J = 9.5 Hz, 1H), 3.11 (d, J = 9.5 Hz, 1H), 2.88 (dd, J = 13.5, 3.0 Hz, 1H), 2.03 (dd, J = 13.5, 10.3 Hz, 1H), 1.93 (d, J = 7.1Hz, 2H), 1.86 - 1.05 (m, 21H), 1.06 - 0.93 (m, 12H), 0.90 - 0.82 (m, 6H), 0.81 (d, J = 11.4 Hz, 1H). LRMS (ESI):727.43 [M+H] + .

[0255] Example 179 (5S,8R,9R,10S,14R,17R,18S)-3-carbonyloleanolic acid-17-(2'R)-(hydroxy)ethyl-β-D-glucuronopyranoside (A179) The remaining raw materials, reagents, and production method were the same as in Example 6, but with the exception of 2,3,4,6-O-tetrabenzyl-1-(pyridin-1-yl)sulfonyl-β-D-thioglucopyranoside being replaced with 2,3,4-O-tribenzyl-1-(pyridin-1-yl)sulfonyl-β-D-thioglucuronopyranoside, and (3S,5S,8R,9R,10S,14R,17R,18S)-28-O-benzyl-3-aldehyde oleanolic acid being replaced with (5S,8R,9R,10S,14R,17R,18S)-3-carbonyl-17-formylmethyl oleanolic acid. A179 (70% yield) was obtained using the same method as in Example 6, using the same raw materials, reagents, and production method as in Example 6. 1H NMR (500 MHz, MeOD) δ 5.28 (s, 1H), 4.16 (s, 1H), 3.79 (d, J = 2.0 Hz, 2H), 3.46 (dd, J = 20.4, 9.3 Hz, 2H), 3.38 (s, 1H), 3.35 - 3.31 (m, 1H), 3.23 (d, J = 9.5 Hz, 1H), 3.11 (d, J = 9.5 Hz, 1H), 2.88 (dd, J = 13.5, 3.0 Hz, 1H), 2.03 (dd, J = 13.5, 10.3 Hz, 1H), 1.93 (d, J = 7.1Hz, 2H), 1.86 - 1.05 (m, 21H), 1.06 - 0.93 (m, 12H), 0.90 - 0.82 (m, 6H), 0.81 (d, J = 11.4 Hz, 1H). LRMS (ESI):631.41 [M+H] + .

[0256] Example 180 (5S,8R,9R,10S,14R,17R,18S)-3-carbonyloleanolic acid-17-(2'R)-(hydroxy)ethyl-2'',3'',4''-O-triacetyl-β-D-glucuronopyranoside (A180) The remaining raw materials, reagents, and preparation method were the same as in Example 6, but with the exception of 2,3,4,6-O-tetrabenzyl-1-(pyridin-1-yl)sulfonyl-β-D-thioglucopyranoside being replaced with 2,3,4-O-triacetyl-1-(pyridin-1-yl)sulfonyl-β-D-thioglucuronopyranoside, and (3S,5S,8R,9R,10S,14R,17R,18S)-28-O-benzyl-3-aldehyde oleanolic acid being replaced with (5S,8R,9R,10S,14R,17R,18S)-3-carbonyl-17-formylmethyl oleanolic acid. A180 (yield 69%) was obtained using the same method as in Example 6. 1H NMR (500 MHz, MeOD) δ 5.28 (s, 1H), 4.16 (s, 1H), 3.79 (d, J = 2.0 Hz, 2H), 3.46 (dd, J = 20.4, 9.3 Hz, 2H), 3.38 (s, 1H), 3.35 - 3.31 (m, 1H), 3.23 (d, J = 9.5 Hz, 1H), 3.11 (d, J = 9.5 Hz, 1H), 2.88 (dd, J = 13.5, 3.0 Hz, 1H), 2.03 (dd, J = 13.5, 10.3 Hz, 1H), 1.93 (d, J = 7.1Hz, 2H), 1.86 - 1.05 (m, 21H), 1.06 - 0.93 (m, 12H), 0.90 - 0.82 (m, 6H), 0.81 (d, J = 11.4 Hz, 1H). LRMS (ESI):757.44 [M+H] + .

[0257] Example 181 (5S,8R,9R,10S,14R,17R,18S)-3-carbonylursolic acid-17-(2'R)-(hydroxy)ethyl-2'',3'',4''-O-triacetyl-β-D-glucuronopyranoside (A181) The remaining raw materials, reagents, and preparation method were the same as in Example 6, but with the exception of 2,3,4,6-O-tetrabenzyl-1-(pyridin-1-yl)sulfonyl-β-D-thioglucopyranoside being replaced with 2,3,4-O-triacetyl-1-(pyridin-1-yl)sulfonyl-β-D-thioglucuronopyranoside, and (3S,5S,8R,9R,10S,14R,17R,18S)-28-O-benzyl-3-aldehyde oleanolic acid being replaced with (5S,8R,9R,10S,14R,17R,18S)-3-carbonyl-17-formylmethylursolic acid. A181 (77% yield) was obtained using the same method as in Example 6. 1H NMR (500 MHz, MeOD) δ 5.28 (s, 1H), 4.16 (s, 1H), 3.79 (d, J = 2.0 Hz, 2H), 3.46 (dd, J = 20.4, 9.3 Hz, 2H), 3.38 (s, 1H), 3.35 - 3.31 (m, 1H), 3.23 (d, J = 9.5 Hz, 1H), 3.11 (d, J = 9.5 Hz, 1H), 2.88 (dd, J = 13.5, 3.0 Hz, 1H), 2.03 (dd, J = 13.5, 10.3 Hz, 1H), 1.93 (d, J = 7.1Hz, 2H), 1.86 - 1.05 (m, 21H), 1.06 - 0.93 (m, 12H), 0.90 - 0.82 (m, 6H), 0.81 (d, J = 11.4 Hz, 1H). LRMS (ESI): 757.44 [M+H] + .

[0258] Example 182 (5S,8R,9R,10S,14R,17R,18S)-3-carbonylbetulinic acid-17-(2'R)-(hydroxy)ethyl-2'',3'',4''-O-triacetyl-β-D-glucuronopyranoside (A182) The remaining raw materials, reagents, and preparation method were the same as in Example 6, but with the exception of 2,3,4,6-O-tetrabenzyl-1-(pyridin-1-yl)sulfonyl-β-D-thioglucopyranoside being replaced with 2,3,4-O-triacetyl-1-(pyridin-1-yl)sulfonyl-β-D-thioglucuronopyranoside, and (3S,5S,8R,9R,10S,14R,17R,18S)-28-O-benzyl-3-aldehyde oleanolic acid being replaced with (5S,8R,9R,10S,14R,17R,18S)-3-carbonyl-17-formylmethyl betulinic acid. A182 (72% yield) was obtained using the same method as in Example 6. 1H NMR (500 MHz, MeOD) δ 5.28 (s, 1H), 4.16 (s, 1H), 3.79 (d, J = 2.0 Hz, 2H), 3.46 (dd, J = 20.4, 9.3 Hz, 2H), 3.38 (s, 1H), 3.35 - 3.31 (m, 1H), 3.23 (d, J = 9.5 Hz, 1H), 3.11 (d, J = 9.5 Hz, 1H), 2.88 (dd, J = 13.5, 3.0 Hz, 1H), 2.03 (dd, J = 13.5, 10.3 Hz, 1H), 1.93 (d, J = 7.1Hz, 2H), 1.86 - 1.05 (m, 21H), 1.06 - 0.93 (m, 12H), 0.90 - 0.82 (m, 6H), 0.81 (d, J = 11.4 Hz, 1H). LRMS (ESI) : 757.44 [M+H] + .

[0259] Example 183 (5S,8R,9R,10S,14R,17R,18S)-3-carbonyloleanolic acid-17-(1'R)-(hydroxy)methyl-6''-deoxy-6''-fluoro-β-D-glucopyranoside (A183) The remaining raw materials, reagents, and production method were the same as in Example 6, but A183 (yield 70%) was obtained. 1H NMR (500 MHz, MeOD) δ 5.28 (s, 1H), 4.16 (s, 1H), 3.79 (d, J = 2.0 Hz, 2H), 3.46 (dd, J = 20.4, 9.3 Hz, 2H), 3.38 (s, 1H), 3.35 - 3.31 (m, 1H), 3.23 (d, J = 9.5 Hz, 1H), 3.11 (d, J = 9.5 Hz, 1H), 2.88 (dd, J = 13.5, 3.0 Hz, 1H), 2.03 (dd, J = 13.5, 10.3 Hz, 1H), 1.93 (d, J = 7.1Hz, 2H), 1.86 - 1.05 (m, 21H), 1.06 - 0.93 (m, 12H), 0.90 - 0.82 (m, 6H), 0.81 (d, J = 11.4 Hz, 1H). LRMS (ESI):605.41 [M+H] + .

[0260] Example 184 (5S,8R,9R,10S,14R,17R,18S)-3-carbonyloleanolic acid-17-methyl-6"-deoxy-6"-fluoro-β-D-glucopyranoside (A184) The remaining raw materials, reagents, and preparation method were the same as in Example 10, but A184 (yield 71%) was obtained. 1H NMR (500 MHz, MeOD) δ 5.28 (s, 1H), 4.16 (s, 1H), 3.79 (d, J = 2.0 Hz, 2H), 3.46 (dd, J = 20.4, 9.3 Hz, 2H), 3.38 (s, 1H), 3.35 - 3.31 (m, 1H), 3.23 (d, J = 9.5 Hz, 1H), 3.11 (d, J = 9.5 Hz, 1H), 2.88 (dd, J = 13.5, 3.0 Hz, 1H), 2.03 (dd, J = 13.5, 10.3 Hz, 1H), 1.93 (d, J = 7.1Hz, 2H), 1.86 - 1.05 (m, 21H), 1.06 - 0.93 (m, 12H), 0.90 - 0.82 (m, 6H), 0.81 (d, J = 11.4 Hz, 1H). LRMS (ESI):589.42 [M+H] + .

[0261] Example 185 (3S,5S,8R,9R,10S,14R,17R,18S)-Oleanolic acid-17-(1'R)-(hydroxy)methyl-6''-deoxy-6''-fluoro-β-D-glucopyranoside (A185) The remaining raw materials, reagents, and production method were the same as in Example 6, but A185 (yield 75%) was obtained. 1H NMR (500 MHz, MeOD) δ 5.28 (s, 1H), 4.16 (s, 1H), 3.79 (d, J = 2.0 Hz, 2H), 3.46 (dd, J = 20.4, 9.3 Hz, 2H), 3.38 (s, 1H), 3.35 - 3.31 (m, 1H), 3.23 (d, J = 9.5 Hz, 1H), 3.11 (d, J = 9.5 Hz, 1H), 2.88 (dd, J = 13.5, 3.0 Hz, 1H), 2.03 (dd, J = 13.5, 10.3 Hz, 1H), 1.93 (d, J = 7.1Hz, 2H), 1.86 - 1.05 (m, 21H), 1.06 - 0.93 (m, 1H), 0.90 - 0.82 (m, 6H), 0.81 (d, J = 11.4 Hz, 1H). LRMS (ESI):607.43 [M+H] + .

[0262] Example 186 (5S,8R,9R,10S,14R,17R,18S)-3-carbonyloleanolic acid-17-(1'R)-(hydroxy)methyl-2'',3'',4''-O-triacetyl-6''-deoxy-6''-fluoro-β-D-glucopyranoside (A186) The remaining raw materials, reagents, and preparation method were the same as in Example 6, but with the exception of 2,3,4,6-O-tetrabenzyl-1-(pyridin-1-yl)sulfonyl-β-D-thioglucopyranoside being replaced with 2,3,4-O-triacetyl-1-(pyridin-1-yl)sulfonyl-6-deoxy-6-fluoro-β-D-thioglucopyranoside, and (3S,5S,8R,9R,10S,14R,17R,18S)-28-O-benzyl-3-aldehyde oleanolic acid being replaced with (5S,8R,9R,10S,14R,17R,18S)-3-carbonyl-17-aldehyde oleanolic acid. A186 (70% yield) was obtained using the same method as in Example 6. 1H NMR (500 MHz, MeOD) δ 5.28 (s, 1H), 4.16 (s, 1H), 3.79 (d, J = 2.0 Hz, 2H), 3.46 (dd, J = 20.4, 9.3 Hz, 2H), 3.38 (s, 1H), 3.35 - 3.31 (m, 1H), 3.23 (d, J = 9.5 Hz, 1H), 3.11 (d, J = 9.5 Hz, 1H), 2.88 (dd, J = 13.5, 3.0 Hz, 1H), 2.03 (dd, J = 13.5, 10.3 Hz, 1H), 1.93 (d, J = 7.1Hz, 2H), 1.86 - 1.05 (m, 21H), 1.06 - 0.93 (m, 12H), 0.90 - 0.82 (m, 6H), 0.81 (d, J = 11.4 Hz, 1H). LRMS (ESI):731.45 [M+H] + .

[0263] Example 187 (5S,8R,9R,10S,14R,17R,18S)-3-carbonyloleanolic acid-17-methyl-2'',3'',4''-O-triacetyl-6''-deoxy-6''-fluoro-β-D-glucopyranoside (A187) The remaining raw materials, reagents, and production method were the same as in Example 10, but A187 (yield 75%) was obtained. 1H NMR (500 MHz, MeOD) δ 5.28 (s, 1H), 4.16 (s, 1H), 3.79 (d, J = 2.0 Hz, 2H), 3.46 (dd, J = 20.4, 9.3 Hz, 2H), 3.38 (s, 1H), 3.35 - 3.31 (m, 1H), 3.23 (d, J = 9.5 Hz, 1H), 3.11 (d, J = 9.5 Hz, 1H), 2.88 (dd, J = 13.5, 3.0 Hz, 1H), 2.03 (dd, J = 13.5, 10.3 Hz, 1H), 1.93 (d, J = 7.1Hz, 2H), 1.86 - 1.05 (m, 21H), 1.06 - 0.93 (m, 12H), 0.90 - 0.82 (m, 6H), 0.81 (d, J = 11.4 Hz, 1H). LRMS (ESI):715.45 [M+H] + .

[0264] Example 188 (5S,8R,9R,10S,14R,17R,18S)-3-carbonyloleanolic acid-17-(2'R)-(hydroxy)ethyl-6''-deoxy-6''-fluoro-β-D-glucopyranoside (A188) The remaining raw materials, reagents, and preparation method were the same as in Example 6, but A188 (yield 76%) was obtained. 1H NMR (500 MHz, MeOD) δ 5.28 (s, 1H), 4.16 (s, 1H), 3.79 (d, J = 2.0 Hz, 2H), 3.46 (dd, J = 20.4, 9.3 Hz, 2H), 3.38 (s, 1H), 3.35 - 3.31 (m, 1H), 3.23 (d, J = 9.5 Hz, 1H), 3.11 (d, J = 9.5 Hz, 1H), 2.88 (dd, J = 13.5, 3.0 Hz, 1H), 2.03 (dd, J = 13.5, 10.3 Hz, 1H), 1.93 (d, J = 7.1Hz, 2H), 1.86 - 1.05 (m, 21H), 1.06 - 0.93 (m, 12H), 0.90 - 0.82 (m, 6H), 0.81 (d, J = 11.4 Hz, 1H). LRMS (ESI):619.43 [M+H] + .

[0265] Example 189 (5S,8R,9R,10S,14R,17R,18S)-3-carbonyloleanolic acid-17-(2'R)-(hydroxy)ethyl-2'',3'',4''-O-triacetyl-6''-deoxy-6''-fluoro-β-D-glucopyranoside (A189) The remaining raw materials, reagents, and production method were the same as in Example 6, but A189 (yield 69%) was obtained. 1H NMR (500 MHz, MeOD) δ 5.28 (s, 1H), 4.16 (s, 1H), 3.79 (d, J = 2.0 Hz, 2H), 3.46 (dd, J = 20.4, 9.3 Hz, 2H), 3.38 (s, 1H), 3.35 - 3.31 (m, 1H), 3.23 (d, J = 9.5 Hz, 1H), 3.11 (d, J = 9.5 Hz, 1H), 2.88 (dd, J = 13.5, 3.0 Hz, 1H), 2.03 (dd, J = 13.5, 10.3 Hz, 1H), 1.93 (d, J = 7.1Hz, 2H), 1.86 - 1.05 (m, 21H), 1.06 - 0.93 (m, 12H), 0.90 - 0.82 (m, 6H), 0.81 (d, J = 11.4 Hz, 1H). LRMS (ESI):745.46 [M+H] + .

[0266] Example 190 (5S,8R,9R,10S,14R,17R,18S)-3-carbonylursolic acid-17-(2'R)-(hydroxy)ethyl-2'',3'',4''-O-triacetyl-6''-deoxy-6''-fluoro-β-D-glucopyranoside (A190) The remaining raw materials, reagents, and preparation method were the same as in Example 6, but with the exception of 2,3,4,6-O-tetrabenzyl-1-(pyridin-1-yl)sulfonyl-β-D-thioglucopyranoside being replaced with 2,3,4-O-triacetyl-1-(pyridin-1-yl)sulfonyl-6-deoxy-6-fluoro-β-D-thioglucopyranoside, and (3S,5S,8R,9R,10S,14R,17R,18S)-28-O-benzyl-3-aldehyde oleanolic acid being replaced with (5S,8R,9R,10S,14R,17R,18S)-3-carbonyl-17-formylmethylursolic acid. A190 (yield 67%) was obtained using the same method as in Example 6. 1H NMR (500 MHz, MeOD) δ 5.28 (s, 1H), 4.16 (s, 1H), 3.79 (d, J = 2.0 Hz, 2H), 3.46 (dd, J = 20.4, 9.3 Hz, 2H), 3.38 (s, 1H), 3.35 - 3.31 (m, 1H), 3.23 (d, J = 9.5 Hz, 1H), 3.11 (d, J = 9.5 Hz, 1H), 2.88 (dd, J = 13.5, 3.0 Hz, 1H), 2.03 (dd, J = 13.5, 10.3 Hz, 1H), 1.93 (d, J = 7.1Hz, 2H), 1.86 - 1.05 (m, 21H), 1.06 - 0.93 (m, 12H), 0.90 - 0.82 (m, 6H), 0.81 (d, J = 11.4 Hz, 1H). LRMS (ESI): 745.46 [M+H] + .

[0267] Example 191 (5S,8R,9R,10S,14R,17R,18S)-3-carbonylbetulinic acid-17-(2'R)-(hydroxy)ethyl-2'',3'',4''-O-triacetyl-6''-deoxy-6''-fluoro-β-D-glucopyranoside (A191) The remaining raw materials, reagents, and preparation method were the same as in Example 6, but with the exception of 2,3,4,6-O-tetrabenzyl-1-(pyridin-1-yl)sulfonyl-β-D-thioglucopyranoside being replaced with 2,3,4-O-triacetyl-1-(pyridin-1-yl)sulfonyl-6-deoxy-6-fluoro-β-D-thioglucopyranoside, and (3S,5S,8R,9R,10S,14R,17R,18S)-28-O-benzyl-3-aldehyde oleanolic acid being replaced with (5S,8R,9R,10S,14R,17R,18S)-3-carbonyl-17-formylmethyl betulinic acid. A191 (71% yield) was obtained using the same method as in Example 6. 1H NMR (500 MHz, MeOD) δ 5.28 (s, 1H), 4.16 (s, 1H), 3.79 (d, J = 2.0 Hz, 2H), 3.46 (dd, J = 20.4, 9.3 Hz, 2H), 3.38 (s, 1H), 3.35 - 3.31 (m, 1H), 3.23 (d, J = 9.5 Hz, 1H), 3.11 (d, J = 9.5 Hz, 1H), 2.88 (dd, J = 13.5, 3.0 Hz, 1H), 2.03 (dd, J = 13.5, 10.3 Hz, 1H), 1.93 (d, J = 7.1Hz, 2H), 1.86 - 1.05 (m, 21H), 1.06 - 0.93 (m, 12H), 0.90 - 0.82 (m, 6H), 0.81 (d, J = 11.4 Hz, 1H). LRMS (ESI) : 745.46 [M+H] + .

[0268] Example 192 (5S,8R,9R,10S,14R,17R,18S)-3-carbonyloleanolic acid-17-(1'R)-(hydroxy)methyl-β-D-glucopyranoside (A192) The remaining raw materials, reagents, and preparation method were the same as in Example 6, but with the exception of 2,3,4,6-O-tetrabenzyl-1-(pyridin-1-yl)sulfonyl-β-D-thioglucopyranoside, which was replaced with 2,3,4,6-O-tetrabenzyl-1-(pyridin-1-yl)sulfonyl-β-D-thioglucopyranoside, and (3S,5S,8R,9R,10S,14R,17R,18S)-28-O-benzyl-3-aldehyde oleanolic acid, which was replaced with (5S,8R,9R,10S,14R,17R,18S)-3-carbonyl-17-aldehyde oleanolic acid. A192 (70% yield) was obtained using the same method as in Example 6, using the same raw materials, reagents, and preparation method as in Example 6. 1H NMR (500 MHz, MeOD) δ 5.28 (s, 1H), 4.16 (s, 1H), 3.79 (d, J = 2.0 Hz, 2H), 3.46 (dd, J = 20.4, 9.3 Hz, 2H), 3.38 (s, 1H), 3.35 - 3.31 (m, 1H), 3.23 (d, J = 9.5 Hz, 1H), 3.11 (d, J = 9.5 Hz, 1H), 2.88 (dd, J = 13.5, 3.0 Hz, 1H), 2.03 (dd, J = 13.5, 10.3 Hz, 1H), 1.93 (d, J = 7.1Hz, 2H), 1.86 - 1.05 (m, 21H), 1.06 - 0.93 (m, 12H), 0.90 - 0.82 (m, 6H), 0.81 (d, J = 11.4 Hz, 1H). LRMS (ESI):603.42 [M+H] + .

[0269] Example 193 (5S,8R,9R,10S,14R,17R,18S)-3-carbonyloleanolic acid-17-methyl-β-D-glucopyranoside (A193) The remaining raw materials, reagents, and preparation method were the same as in Example 10, but with the exception of 2,3,4,6-O-tetrabenzyl-1-(pyridin-1-yl)sulfonyl-β-D-thioglucopyranoside, which was replaced with 2,3,4,6-O-tetrabenzyl-1-(pyridin-1-yl)sulfonyl-β-D-thioglucopyranoside, and (3S,5S,8R,9R,10S,14R,17R,18S)-28-O-benzyl-3-aldehyde oleanolic acid, which was replaced with (5S,8R,9R,10S,14R,17R,18S)-3-carbonyl-17-aldehyde oleanolic acid. A193 (yield 84%) was obtained using the same method as in Example 10. 1H NMR (500 MHz, MeOD) δ 5.28 (s, 1H), 4.16 (s, 1H), 3.79 (d, J = 2.0 Hz, 2H), 3.46 (dd, J = 20.4, 9.3 Hz, 2H), 3.38 (s, 1H), 3.35 - 3.31 (m, 1H), 3.23 (d, J = 9.5 Hz, 1H), 3.11 (d, J = 9.5 Hz, 1H), 2.88 (dd, J = 13.5, 3.0 Hz, 1H), 2.03 (dd, J = 13.5, 10.3 Hz, 1H), 1.93 (d, J = 7.1Hz, 2H), 1.86 - 1.05 (m, 21H), 1.06 - 0.93 (m, 12H), 0.90 - 0.82 (m, 6H), 0.81 (d, J = 11.4 Hz, 1H). LRMS (ESI):587.42 [M+H] + .

[0270] Example 194 (3S,5S,8R,9R,10S,14R,17R,18S)-Oleanolic acid-17-(1'R)-(hydroxy)methyl-β-D-glucopyranoside (A194) The remaining raw materials, reagents, and preparation method were the same as in Example 6, but with the exception of 2,3,4,6-O-tetrabenzyl-1-(pyridin-1-yl)sulfonyl-β-D-thioglucopyranoside, which was replaced with 2,3,4,6-O-tetrabenzyl-1-(pyridin-1-yl)sulfonyl-β-D-thioglucopyranoside, and (3S,5S,8R,9R,10S,14R,17R,18S)-28-O-benzyl-3-aldehyde oleanolic acid, which was replaced with (5S,8R,9R,10S,14R,17R,18S)-3-hydroxy-17-aldehyde oleanolic acid. A194 (79% yield) was obtained using the same method as in Example 6, using the same raw materials, reagents, and preparation method as in Example 6. 1H NMR (500 MHz, MeOD) δ 5.28 (s, 1H), 4.16 (s, 1H), 3.79 (d, J = 2.0 Hz, 2H), 3.46 (dd, J = 20.4, 9.3 Hz, 2H), 3.38 (s, 1H), 3.35 - 3.31 (m, 1H), 3.23 (d, J = 9.5 Hz, 1H), 3.11 (d, J = 9.5 Hz, 1H), 2.88 (dd, J = 13.5, 3.0 Hz, 1H), 2.03 (dd, J = 13.5, 10.3 Hz, 1H), 1.93 (d, J = 7.1Hz, 2H), 1.86 - 1.05 (m, 21H), 1.06 - 0.93 (m, 1H), 0.90 - 0.82 (m, 6H), 0.81 (d, J = 11.4 Hz, 1H). LRMS (ESI):605.43[M+H] + .

[0271] Example 195 (5S,8R,9R,10S,14R,17R,18S)-3-carbonyloleanolic acid-17-(1'R)-(hydroxy)methyl-2'',3'',4'',6''-O-tetraacetyl-β-D-glucopyranoside (A195) The remaining raw materials, reagents, and production method were the same as in Example 6, but with the exception of 2,3,4,6-O-tetrabenzyl-1-(pyridin-1-yl)sulfonyl-β-D-thioglucopyranoside being replaced with 2,3,4,6-O-tetraacetyl-1-(pyridin-1-yl)sulfonyl-β-D-thioglucopyranoside, and (3S,5S,8R,9R,10S,14R,17R,18S)-28-O-benzyl-3-aldehyde oleanolic acid being replaced with (5S,8R,9R,10S,14R,17R,18S)-3-carbonyl-17-aldehyde oleanolic acid. A195 (79% yield) was obtained using the same method as in Example 6, using the same starting materials, reagents, and production method as in Example 6. 1H NMR (500 MHz, MeOD) δ 5.28 (s, 1H), 4.16 (s, 1H), 3.79 (d, J = 2.0 Hz, 2H), 3.46 (dd, J = 20.4, 9.3 Hz, 2H), 3.38 (s, 1H), 3.35 - 3.31 (m, 1H), 3.23 (d, J = 9.5 Hz, 1H), 3.11 (d, J = 9.5 Hz, 1H), 2.88 (dd, J = 13.5, 3.0 Hz, 1H), 2.03 (dd, J = 13.5, 10.3 Hz, 1H), 1.93 (d, J = 7.1Hz, 2H), 1.86 - 1.05 (m, 21H), 1.06 - 0.93 (m, 12H), 0.90 - 0.82 (m, 6H), 0.81 (d, J = 11.4 Hz, 1H). LRMS (ESI):771.46 [M+H] + .

[0272] Example 196 (5S,8R,9R,10S,14R,17R,18S)-3-carbonyloleanolic acid-17-methyl-2'',3'',4'',6''-O-tetraacetyl-β-D-glucopyranoside (A196) The remaining raw materials, reagents, and preparation method were the same as in Example 10, except that 2,3,4,6-O-tetrabenzyl-1-(pyridin-1-yl)sulfonyl-β-D-thioglucopyranoside was replaced with 2,3,4,6-O-tetraacetyl-1-(pyridin-1-yl)sulfonyl-β-D-thioglucopyranoside, and (3S,5S,8R,9R,10S,14R,17R,18S)-28-O-benzyl-3-aldehyde oleanolic acid was replaced with (5S,8R,9R,10S,14R,17R,18S)-3-carbonyl-17-aldehyde oleanolic acid. A196 (yield 78%) was obtained using the same method as in Example 10. 1H NMR (500 MHz, MeOD) δ 5.28 (s, 1H), 4.16 (s, 1H), 3.79 (d, J = 2.0 Hz, 2H), 3.46 (dd, J = 20.4, 9.3 Hz, 2H), 3.38 (s, 1H), 3.35 - 3.31 (m, 1H), 3.23 (d, J = 9.5 Hz, 1H), 3.11 (d, J = 9.5 Hz, 1H), 2.88 (dd, J = 13.5, 3.0 Hz, 1H), 2.03 (dd, J = 13.5, 10.3 Hz, 1H), 1.93 (d, J = 7.1Hz, 2H), 1.86 - 1.05 (m, 21H), 1.06 - 0.93 (m, 12H), 0.90 - 0.82 (m, 6H), 0.81 (d, J = 11.4 Hz, 1H). LRMS (ESI):755.47 [M+H] + .

[0273] Example 197 (5S,8R,9R,10S,14R,17R,18S)-3-carbonyloleanolic acid-17-(2'R)-(hydroxy)ethyl-β-D-glucopyranoside (A197) The remaining raw materials, reagents, and preparation method were the same as in Example 6, but with the exception of 2,3,4,6-O-tetrabenzyl-1-(pyridin-1-yl)sulfonyl-β-D-thioglucopyranoside, which was replaced with 2,3,4,6-O-tetrabenzyl-1-(pyridin-1-yl)sulfonyl-β-D-thioglucopyranoside, and (3S,5S,8R,9R,10S,14R,17R,18S)-28-O-benzyl-3-aldehyde oleanolic acid, which was replaced with (5S,8R,9R,10S,14R,17R,18S)-3-carbonyl-17-formylmethyl oleanolic acid. A197 (75% yield) was obtained using the same method as in Example 6. 1H NMR (500 MHz, MeOD) δ 5.28 (s, 1H), 4.16 (s, 1H), 3.79 (d, J = 2.0 Hz, 2H), 3.46 (dd, J = 20.4, 9.3 Hz, 2H), 3.38 (s, 1H), 3.35 - 3.31 (m, 1H), 3.23 (d, J = 9.5 Hz, 1H), 3.11 (d, J = 9.5 Hz, 1H), 2.88 (dd, J = 13.5, 3.0 Hz, 1H), 2.03 (dd, J = 13.5, 10.3 Hz, 1H), 1.93 (d, J = 7.1Hz, 2H), 1.86 - 1.05 (m, 21H), 1.06 - 0.93 (m, 12H), 0.90 - 0.82 (m, 6H), 0.81 (d, J = 11.4 Hz, 1H). LRMS (ESI):617.43[M+H] + .

[0274] Example 198 (5S,8R,9R,10S,14R,17R,18S)-3-carbonyloleanolic acid-17-(2'R)-(hydroxy)ethyl-2'',3'',4'',6''-O-tetraacetyl-β-D-glucopyranoside (A198) The remaining raw materials, reagents, and preparation method were the same as in Example 6, but with the exception of 2,3,4,6-O-tetrabenzyl-1-(pyridin-1-yl)sulfonyl-β-D-thioglucopyranoside being replaced with 2,3,4,6-O-tetraacetyl-1-(pyridin-1-yl)sulfonyl-β-D-thioglucopyranoside, and (3S,5S,8R,9R,10S,14R,17R,18S)-28-O-benzyl-3-aldehyde oleanolic acid being replaced with (5S,8R,9R,10S,14R,17R,18S)-3-carbonyl-17-formylmethyl oleanolic acid. A198 (72% yield) was obtained using the same method as in Example 6, using the same starting materials, reagents, and preparation method as in Example 6. 1H NMR (500 MHz, MeOD) δ 5.28 (s, 1H), 4.16 (s, 1H), 3.79 (d, J = 2.0 Hz, 2H), 3.46 (dd, J = 20.4, 9.3 Hz, 2H), 3.38 (s, 1H), 3.35 - 3.31 (m, 1H), 3.23 (d, J = 9.5 Hz, 1H), 3.11 (d, J = 9.5 Hz, 1H), 2.88 (dd, J = 13.5, 3.0 Hz, 1H), 2.03 (dd, J = 13.5, 10.3 Hz, 1H), 1.93 (d, J = 7.1Hz, 2H), 1.86 - 1.05 (m, 21H), 1.06 - 0.93 (m, 12H), 0.90 - 0.82 (m, 6H), 0.81 (d, J = 11.4 Hz, 1H). LRMS (ESI):785.48 [M+H] + .

[0275] Example 199 (5S,8R,9R,10S,14R,17R,18S)-3-carbonylursolic acid-17-(2'R)-(hydroxy)ethyl-2'',3'',4'',6''-O-tetraacetyl-β-D-glucopyranoside (A199) The remaining raw materials, reagents, and preparation method were the same as in Example 6, but with the exception of 2,3,4,6-O-tetrabenzyl-1-(pyridin-1-yl)sulfonyl-β-D-thioglucopyranoside being replaced with 2,3,4,6-O-tetraacetyl-1-(pyridin-1-yl)sulfonyl-β-D-thiorhamnopyranoside, and (3S,5S,8R,9R,10S,14R,17R,18S)-28-O-benzyl-3-aldehyde oleanolic acid being replaced with (5S,8R,9R,10S,14R,17R,18S)-3-carbonyl-17-formylmethylursolic acid. A199 (79% yield) was obtained using the same method as in Example 6. 1H NMR (500 MHz, MeOD) δ 5.28 (s, 1H), 4.16 (s, 1H), 3.79 (d, J = 2.0 Hz, 2H), 3.46 (dd, J = 20.4, 9.3 Hz, 2H), 3.38 (s, 1H), 3.35 - 3.31 (m, 1H), 3.23 (d, J = 9.5 Hz, 1H), 3.11 (d, J = 9.5 Hz, 1H), 2.88 (dd, J = 13.5, 3.0 Hz, 1H), 2.03 (dd, J = 13.5, 10.3 Hz, 1H), 1.93 (d, J = 7.1Hz, 2H), 1.86 - 1.05 (m, 21H), 1.06 - 0.93 (m, 12H), 0.90 - 0.82 (m, 6H), 0.81 (d, J = 11.4 Hz, 1H). LRMS (ESI): 785.48 [M+H] + .

[0276] Example 200 (5S,8R,9R,10S,14R,17R,18S)-3-carbonylbetulinic acid-17-(2'R)-(hydroxy)ethyl-2'',3'',4'',6''-O-tetraacetyl-β-D-glucopyranoside (A200) The remaining raw materials, reagents, and preparation method were the same as in Example 6, except that 2,3,4,6-O-tetrabenzyl-1-(pyridin-1-yl)sulfonyl-β-D-thioglucopyranoside was replaced with 2,3,4,6-O-tetraacetyl-1-(pyridin-1-yl)sulfonyl-β-D-thiorhamnopyranoside, and (3S,5S,8R,9R,10S,14R,17R,18S)-28-O-benzyl-3-aldehyde oleanolic acid was replaced with (5S,8R,9R,10S,14R,17R,18S)-3-carbonyl-17-formylmethyl betulinic acid. A200 (yield 77%) was obtained using the same method as in Example 6. 1H NMR (500 MHz, MeOD) δ 5.28 (s, 1H), 4.16 (s, 1H), 3.79 (d, J = 2.0 Hz, 2H), 3.46 (dd, J = 20.4, 9.3 Hz, 2H), 3.38 (s, 1H), 3.35 - 3.31 (m, 1H), 3.23 (d, J = 9.5 Hz, 1H), 3.11 (d, J = 9.5 Hz, 1H), 2.88 (dd, J = 13.5, 3.0 Hz, 1H), 2.03 (dd, J = 13.5, 10.3 Hz, 1H), 1.93 (d, J = 7.1Hz, 2H), 1.86 - 1.05 (m, 21H), 1.06 - 0.93 (m, 12H), 0.90 - 0.82 (m, 6H), 0.81 (d, J = 11.4 Hz, 1H). LRMS (ESI) : 785.48 [M+H] + .

[0277] Example 201 (5S,8R,9R,10S,14R,17R,18S)-3-carbonyloleanolic acid-28-β-D-glucopyranoside (A201) The compound (3S,5S,8R,9R,10S,14R,17R,18S)-28-O-benzyl-3-aldehyde oleanolic acid was replaced with (5S,8R,9R,10S,14R,17R,18S)-3-carbonyl-17-formyl oleanolic acid. The remaining raw materials, reagents, and production method were the same as in Example 10, and A201 (yield 72%) was obtained. 1H NMR (500 MHz, CDCl3) δ 5.48 (d, J = 5.9 Hz, 1H), 5.33 (tdd, J = 5.1, 1.8, 1.1 Hz, 1H), 5.07 (d, J = 5.7 Hz, 1H), 4.57 (d, J = 6.3 Hz, 1H), 4.44 (dd, J = 8.8, 2.6 Hz, 1H), 4.19 (t, J = 4.5 Hz, 1H), 3.71 - 3.58 (m, 3H), 3.58 (dt, J = 7.7, 3.5 Hz, 1H), 3.58 - 3.49 (m, 1H), 3.31 (dddd, J = 8.5, 7.8, 5.8, 1.8 Hz, 1H), 2.48 (ddd, J = 12.5, 6.5, 4.0 Hz, 1H), 2.40 (ddd, J = 12.5, 6.6, 4.0 Hz, 1H), 2.17 (tq, J = 5.1, 1.0 Hz, 1H), 2.04 (dddd, J = 12.6, 6.4, 5.1, 1.0 Hz, 1H), 1.95 - 1.87 (m, 1H), 1.91 - 1.84 (m, 1H), 1.86 - 1.81 (m, 1H), 1.84 - 1.78 (m, 2H), 1.72 - 1.59 (m, 6H), 1.62 - 1.48 (m, 3H), 1.51 - 1.41 (m, 1H), 1.44 - 1.36 (m, 2H), 1.40 - 1.33 (m, 1H), 1.36 - 1.29 (m, 1H), 1.15 (s, 2H), 1.08 (t, J = 1.6 Hz, 5H), 0.99 - 0.92 (m, 6H), 0.93 (d, J = 6.6 Hz, 5H). LRMS (ESI):601.4 [M+H] + .

[0278] Example 202 (5S, 8R, 9R, 10S, 14R, 17R, 18S)-3-カルボニルウルソール acid-28-β-D-グルコピラノシド (A202) The compound (3S,5S,8R,9R,10S,14R,17R,18S)-28-O-benzyl-3-aldehyde oleanolic acid was replaced with (5S,8R,9R,10S,14R,17R,18S)-3-carbonyl-17-formylursolic acid. The remaining raw materials, reagents, and production method were the same as in Example 10, and A202 (yield 72%) was obtained. 1 H NMR (500 MHz, CDCl3) δ 5.53 - 5.46 (m, 2H), 5.07 (d, J = 5.7 Hz, 1H), 4.57 (d, J = 6.3 Hz, 1H), 4.51 (dd, J = 8.8, 2.6 Hz, 1H), 4.19 (t, J = 4.5 Hz, 1H), 3.71 - 3.58 (m, 3H), 3.58 (dt, J = 7.7, 3.5 Hz, 1H), 3.58 - 3.49 (m, 1H), 3.31 (dddd, J = 8.4, 7.8, 5.8, 1.8 Hz, 1H), 2.48 (ddd, J = 12.5, 6.5, 4.0 Hz, 1H), 2.40 (ddd, J = 12.5, 6.6, 4.0 Hz, 1H), 2.28 - 2.22 (m, 1H), 2.06 - 1.91 (m, 2H), 1.89 - 1.78 (m, 4H), 1.77 (ddd, J = 12.5, 7.7, 5.2 Hz, 1H), 1.73 - 1.57 (m, 5H), 1.60 - 1.54 (m, 1H), 1.57 - 1.51 (m, 1H), 1.48 - 1.41 (m, 1H), 1.44 - 1.38 (m, 2H), 1.41 - 1.35 (m, 1H), 1.35 (dtd, J = 6.5, 3.2, 1.6 Hz, 1H), 1.34 - 1.25 (m, 1H), 1.20 (s, 2H), 1.08 (t, J = 1.6 Hz, 5H), 0.99 - 0.90 (m, 9H), 0.91 (d, J = 2.0 Hz, 2H). LRMS (ESI):601.4 [M+H] + .

[0279] Example 203 (5S,8R,9R,10S,14R,17R,18S)-3-carbonylursolic acid-17-(1'R)-(hydroxy)methyl-β-D-glucopyranoside (A203) The compound (3S,5S,8R,9R,10S,14R,17R,18S)-28-O-benzyl-3-aldehyde oleanolic acid was replaced with (5S,8R,9R,10S,14R,17R,18S)-3-carbonyl-17-formylursolic acid. The remaining raw materials, reagents, and production method were the same as in Example 2, and A203 (yield 64%) was obtained. 1 H NMR (500 MHz,CDCl3) δ 5.47 (tdd, J = 4.9, 1.7, 1.0 Hz, 1H), 4.95 (d, J = 5.3 Hz, 1H), 4.81 (dd, J = 11.0, 5.7 Hz, 2H), 4.61 (d, J = 6.2 Hz, 1H), 4.20 (t, J = 4.5 Hz, 1H), 4.00 - 3.88 (m, 2H), 3.72 (dddd, J = 8.8, 7.9, 6.1, 2.8 Hz, 1H), 3.70 - 3.65 (m, 1H), 3.68 - 3.55 (m, 4H), 2.48 (ddd, J = 12.5, 6.5, 4.0 Hz, 1H), 2.40 (ddd, J = 12.5, 6.6, 4.0 Hz, 1H), 2.06 - 1.86 (m, 4H), 1.84 (ddd, J = 6.6, 2.9, 1.5 Hz, 1H), 1.84 - 1.78 (m, 1H), 1.71 - 1.64 (m, 1H), 1.65 (dd, J = 3.9, 1.6 Hz, 1H), 1.66 - 1.54 (m, 4H), 1.57 - 1.51 (m, 1H), 1.54 - 1.44 (m, 1H), 1.47 - 1.39 (m, 2H), 1.42 - 1.35 (m, 3H), 1.37 - 1.32 (m, 1H), 1.35 - 1.25 (m, 1H), 1.11 - 1.05 (m, 8H), 0.99 - 0.88 (m, 11H). LRMS (ESI):603.4 [M+H] + .

[0280] Example 204 (3S,5S,8R,9R,10S,14R,17R,18S)-Ursolic acid-17-(1'R)-(hydroxy)methyl-β-D-glucopyranoside (A204) The compound (3S,5S,8R,9R,10S,14R,17R,18S)-28-O-benzyl-3-aldehyde oleanolic acid was replaced with (3S,5S,8R,9R,10S,14R,17R,18S)-17-formylursolic acid. The remaining raw materials, reagents, and production method were the same as in Example 2, and A204 (yield 50%) was obtained. 1 H NMR (500 MHz, CDCl3) δ 5.47 (tdd, J = 4.9, 1.7, 1.0 Hz, 1H), 4.95 (d, J = 5.3 Hz, 1H), 4.81 (dd, J = 11.0, 5.7 Hz, 2H), 4.61 (d, J = 6.2 Hz, 1H), 4.20 (t, J = 4.5 Hz, 1H), 4.00 - 3.88 (m, 2H), 3.76 - 3.55 (m, 6H), 3.31 - 3.23 (m, 1H), 3.00 (d, J = 10.8 Hz, 1H), 2.01 - 1.86 (m, 4H), 1.74 - 1.25 (m, LRMS (ESI):605.4 [M+H] + .

[0281] Example 205 (3S,5S,8R,9R,10S,14R,17R,18S)-Ursolic acid-28-β-D-glucopyranoside (A205) The compound (3S,5S,8R,9R,10S,14R,17R,18S)-28-O-benzyl-3-aldehyde oleanolic acid was replaced with (3S,5S,8R,9R,10S,14R,17R,18S)-17-formylursolic acid. The remaining raw materials, reagents, and production method were the same as in Example 10, and A205 (yield 50%) was obtained. 1H NMR (500 MHz, CDCl3) δ 5.53 - 5.46 (m, 2H), 5.07 (d, J = 5.7 Hz, 1H), 4.57 (d, J = 6.3 Hz, 1H), 4.51 (dd, J = 8.8, 2.6 Hz, 1H), 4.19 (t, J = 4.5 Hz, 1H), 3.71 - 3.49 (m, 5H), 3.36 - 3.23 (m, 2H), 3.00 (d, J = 10.8 Hz, 1H), 2.28 - 2.22 (m, 1H), 2.01 - 1.93 (m, 1H), 1.89 - 1.24 (m, 20H), 1.20 (s, 2H), 0.99 - 0.87 (m, 16H). LRMS (ESI):603.4 [M+H] + .

[0282] Example 206 (3S,5S,8R,9R,10S,14R,17R,18S)-oleanolic acid 28-β-D-glucopyranoside (A206) The compound (3S,5S,8R,9R,10S,14R,17R,18S)-28-O-benzyl-3-aldehyde oleanolic acid was replaced with (3S,5S,8R,9R,10S,14R,17R,18S)-17-formyl oleanolic acid. The remaining raw materials, reagents, and production method were the same as in Example 10, and A206 (yield 50%) was obtained. 1H NMR (500 MHz, CDCl3) δ 5.48 (d, J = 5.9 Hz, 1H), 5.33 (tdd, J = 5.1, 1.8, 1.1 Hz, 1H), 5.07 (d, J = 5.7 Hz, 1H), 4.57 (d, J = 6.3 Hz, 1H), 4.44 (dd, J = 8.8, 2.6 Hz, 1H), 4.19 (t, J = 4.5 Hz, 1H), 3.71 - 3.58 (m, 3H), 3.58 (dt, J = 7.7, 3.5 Hz, 1H), 3.58 - 3.49 (m, 1H), 3.36 - 3.23 (m, 2H), 3.00 (d, J = 10.8 Hz, 1H), 2.17 (tq, J = 5.1, 1.0 Hz, 1H), 2.05 (dddd, J = 12.5, 6.2, 5.1, 1.0 Hz, 1H), 1.96 - 1.78 (m, 3H), 1.74 - 1.39 (m, 15H), 1.42 - 1.27 (m, 4H), 1.15 (s, 2H), 0.99 - 0.87 (m, 17H). LRMS (ESI):603.4 [M+H] + .

[0283] Example 207 (3S,5S,8R,9R,10S,13R,14R,17S,18R,19R)-Betulinic acid-28-β-D-glucopyranoside (A207) The compound (3S,5S,8R,9R,10S,14R,17R,18S)-28-O-benzyl-3-aldehyde oleanolic acid was replaced with (3S,5S,8R,9R,10S,14R,17R,18S)-17-formyl betulinic acid. The remaining raw materials, reagents, and production method were the same as in Example 10, and A207 (yield 55%) was obtained. 1H NMR (500 MHz, CDCl3) δ 5.48 (d, J = 5.9 Hz, 1H), 5.07 (d, J = 5.7 Hz, 1H), 4.83 (h, J = 1.6 Hz, 1H), 4.67 (h, J = 1.5 Hz, 1H), 4.57 (d, J = 6.3 Hz, 1H), 4.47 (dd, J = 8.8, 2.5 Hz, 1H), 4.19 (t, J = 4.5 Hz, 1H), 3.72 - 3.49 (m, 5H), 3.36 - 3.23 (m, 2H), 3.04 - 2.96 (m, 2H), 1.82 - 1.48 (m, 22H), 1.51 - 1.47 (m, 1H), 1.50 - 1.43 (m, 1H), 1.45 - 1.35 (m, 1H), 1.31 (ddq, J = 6.8, 4.0, 1.5 Hz, 1H), 1.18 (ddp, J = 7.4, 4.4, 1.5 Hz, 1H), 0.99 - 0.91 (m, 11H), 0.82 (t, J = 1.5 Hz, 3H). LRMS (ESI):603.4 [M+H] + .

[0284] Example 208 (3S,5S,8R,9R,10S,13R,14R,17S,18R,19R)-Betulinic acid-17-(1'R)-(hydroxy)methyl-β-D-glucopyranoside (A208) The compound (3S,5S,8R,9R,10S,14R,17R,18S)-28-O-benzyl-3-aldehyde oleanolic acid was replaced with (3S,5S,8R,9R,10S,14R,17R,18S)-17-formyl betulinic acid. The remaining raw materials, reagents, and production method were the same as in Example 2, and A208 (yield 56%) was obtained. 1H NMR (500 MHz, CDCl3) δ 4.95 (d, J = 5.1 Hz, 1H), 4.84 - 4.79 (m, 2H), 4.69 (d, J = 5.3 Hz, 1H), 4.65 (h, J = 1.6 Hz, 1H), 4.61 (d, J = 6.2 Hz, 1H), 4.20 (t, J = 4.5 Hz, 1H), 3.93 (dddd, J = 8.6, 7.6, 5.9, 1.8 Hz, 1H), 3.85 (ddd, J = 7.7, 5.1, 2.8 Hz, 1H), 3.72 (dddd, J = 8.8, 7.5, 6.0, 2.9Hz, 1H), 3.71 - 3.64 (m, 1H), 3.68 - 3.61 (m, 2H), 3.64 - 3.58 (m, 1H), 3.57 (ddd, J = 12.3, 4.6, 3.3 Hz, 1H), 3.31 - 3.23 (m, 1H), 2.18 - 2.09 (m, 1H), 1.76 - 1.27 (m, 25H), 1.18 (ddp, J = 7.4, 4.4, 1.5 Hz, 1H), 0.99 - 0.90 (m, 11H), 0.82 (t, J = 1.5 Hz, 3H). LRMS (ESI):605.4 [M+H] + .

[0285] Example 209 (5S,8R,9R,10S,13R,14R,17S,18R,19R)-3-carbonylbetulinic acid-17-(1'R)-(hydroxy)methyl-β-D-glucopyranoside (A209) The compound (3S,5S,8R,9R,10S,14R,17R,18S)-28-O-benzyl-3-aldehyde oleanolic acid was replaced with (5S,8R,9R,10S,14R,17R,18S)-3-carbonyl-17-formyl betulinic acid. The remaining raw materials, reagents, and production method were the same as in Example 2, and A209 (yield 60%) was obtained. 1H NMR (500 MHz, CDCl3) δ 4.84 - 4.79 (m, 1H), 4.71 - 4.59 (m, 1H), 3.76 - 3.53 (m, 2H), 2.53 - 2.41 (m, 1H), 1.86 - 1.76 (m, 1H), 1.73 (q, J = 1.4 Hz, 1H), 1.63 - 1.28 (m, 7H), 1.13 - 1.05 (m, 2H), 0.97 (d, J = 1.5 Hz, 1H), 0.92 (d, J = 1.5 Hz, 1H), 0.85 (t, J = 1.4 Hz, 1H).LRMS (ESI):603.4 [M+H] + .

[0286] Example 210 (5S,8R,9R,10S,13R,14R,17S,18R,19R)-3-carbonylbetulinic acid-28-β-D-glucopyranoside (A210) The compound (3S,5S,8R,9R,10S,14R,17R,18S)-28-O-benzyl-3-aldehyde oleanolic acid was replaced with (5S,8R,9R,10S,14R,17R,18S)-3-carbonyl-17-formyl betulinic acid. The remaining raw materials, reagents, and production method were the same as in Example 10, and A210 (yield 51%) was obtained. 1H NMR (500 MHz, CDCl3) δ 5.48 (d, J = 5.9 Hz, 1H), 5.07 (d, J = 5.7 Hz, 1H), 4.83 (h, J = 1.6 Hz, 1H), 4.67 (h, J = 1.5 Hz, 1H), 4.57 (d, J = 6.3 Hz, 1H), 4.47 (dd, J = 8.8, 2.5 Hz, 1H), 4.19 (t, J = 4.5 Hz, 1H), 3.72 - 3.49 (m, 5H), 3.31 (dddd, J = 8.4, 7.7, 5.8, 1.8 Hz, 1H), 3.00 (dddt, J = 10.3, 5.0, 3.3, 1.6 Hz, 1H), 2.53 - 2.41 (m, 2H), 1.86 - 1.59 (m, 11H), 1.62 - 1.57 (m, 1H), 1.59 - 1.53 (m, 2H), 1.51 (ddddd, J = 12.4, 7.7, 6.5, 2.6, 1.4 Hz, 7H), 1.50 - 1.40 (m, 3H), 1.44 - 1.34 (m, 2H), 1.13 - 1.05 (m, 7H), 0.96 (dd, J = 12.7, 1.5 Hz, 6H), 0.85 (t, J = 1.4Hz, 3H).LRMS (ESI):601.4 [M+H] + .

[0287] Example 211 (5S,8R,9R,10S,13R,14R,17S,18R,19R)-3-carbonylbetulinic acid-17-methyl-β-D-glucopyranoside (A211) The compound (3S,5S,8R,9R,10S,14R,17R,18S)-28-O-benzyl-3-aldehyde oleanolic acid was replaced with (5S,8R,9R,10S,14R,17R,18S)-3-carbonyl-17-formyl betulinic acid. The remaining raw materials, reagents, and production method were the same as in Example 6, and A211 (yield 61%) was obtained. 1H NMR (500 MHz, CDCl3) δ 4.85 (d, J = 5.9 Hz, 1H), 4.83 - 4.78 (m, 2H), 4.65 (h, J = 1.5 Hz, 1H), 4.61 (d, J = 6.4 Hz, 1H), 4.23 - 4.16 (m, 1H), 3.88 (ddtd, J = 32.6, 9.0, 7.5, 2.1 Hz, 2H), 3.73 (dddd, J = 8.8, 7.7, 6.2, 2.2 Hz, 1H), 3.70 - 3.63 (m, 2H), 3.60 - 3.51 (m, 2H), 2.53 - 2.41 (m, 2H), 2.23 (dtq, J = 7.0, 5.3, 1.7 Hz, 1H), 1.96 (dd, J = 13.8, 7.2 Hz, 1H), 1.83 (ddd, J = 5.7, 2.8, 1.4 Hz, 1H), 1.83 - 1.76 (m, 1H), 1.73 (q, J = 1.5 Hz, 3H), 1.70 - 1.60 (m, 1H), 1.63 - 1.57 (m, 1H), 1.59 - 1.54 (m, 1H), 1.57 - 1.44 (m, 10H), 1.47 - 1.42 (m, 1H), 1.44 - 1.37 (m, 3H), 1.40 - 1.33 (m, 1H), 1.21 (dd, J = 6.9, 5.6 Hz, 1H), 1.13 - 1.05 (m, 7H), 0.97 (d, J = 1.5 Hz, 3H), 0.92 (d, J = 1.3 Hz, 3H), 0.85 (t, J = 1.5 Hz, 3H). LRMS (ESI):587.4[M+H] + .

[0288] Example 212 (5S, 8R, 9R, 10S, 14R, 17R, 18S)-3-カルボニウルソール acid-17-メチル-β-D-グルコピラノシド (A212) The compound (3S,5S,8R,9R,10S,14R,17R,18S)-28-O-benzyl-3-aldehyde oleanolic acid was replaced with (5S,8R,9R,10S,14R,17R,18S)-3-carbonyl-17-formylursolic acid. The remaining raw materials, reagents, and production method were the same as in Example 6, and A212 (yield 57%) was obtained. 1 H NMR (500 MHz, CDCl3) δ 5.45 (tdd, J = 4.9, 1.8, 1.1 Hz, 1H), 4.85 (d, J = 5.9 Hz, 1H), 4.80 (d, J = 5.7 Hz, 1H), 4.61 (d, J = 6.4 Hz, 1H), 4.23 - 4.17 (m, 1H), 3.96 - 3.88 (m, 1H), 3.84 (dtd, J = 9.3, 7.0, 2.3 Hz, 1H), 3.73 (dddd, J = 8.9, 7.9, 6.3, 2.3 Hz, 1H), 3.70 - 3.62 (m, 2H), 3.62 - 3.51 (m, 2H), 2.48 (ddd, J = 12.5, 6.5, 4.0 Hz, 1H), 2.40 (ddd, J = 12.5, 6.6, 4.0 Hz, 1H), 2.07 - 2.01 (m, 1H), 2.04 - 1.98 (m, 1H), 1.96 (dddd, J = 12.5, 6.3, 4.9, 1.0 Hz, 1H), 1.84 (ddd, J = 6.6, 2.9, 1.5 Hz, 1H), 1.84 - 1.78 (m, 1H), 1.80 - 1.70 (m, 3H), 1.70 - 1.20 (m, 15H), 1.11 - 1.05 (m, 9H), 0.97 (d, J = 1.5 Hz, 3H), 0.95 - 0.86 (m, 9H). LRMS (ESI):587.4[M+H] + .

[0289] Example 213 (3S,5S,8R,9R,10S,14R,17R,18S)-Oleanolic acid 17-methyl-β-D-glucopyranoside (A213) The compound (3S,5S,8R,9R,10S,14R,17R,18S)-28-O-benzyl-3-aldehyde oleanolic acid was replaced with (3S,5S,8R,9R,10S,14R,17R,18S)-17-formyl oleanolic acid. The remaining raw materials, reagents, and production method were the same as in Example 6, and A213 (yield 56%) was obtained. 1 H NMR (500 MHz, CDCl3) δ 5.26 (tdd, J = 5.3, 1.8, 1.0 Hz, 1H), 4.85 (d, J = 5.9 Hz, 1H), 4.80 (d, J = 5.7 Hz, 1H), 4.61 (d, J = 6.4 Hz, 1H), 4.23 - 4.17 (m, 1H), 3.96 - 3.87 (m, 1H), 3.84 - 3.70 (m, 2H), 3.70 - 3.62 (m, 2H), 3.62 - 3.51 (m, 2H), 3.31 - 3.23 (m, 1H), 3.00 (d, J = 10.8 Hz, 1H), 2.68 (tq, J = 4.8, 1.0 Hz, 1H), 2.03 (dd, J = 14.0, 6.7 Hz, 1H), 1.85 (dddd, J = 12.7, 6.4, 5.2, 1.0 Hz, 1H), 1.76 (dddd, J = 12.5, 6.4, 5.1, 1.0 Hz, 1H), 1.74 - 1.20 (m, 22H), 1.09 (s, 2H), 0.99 - 0.87 (m, 17H). LRMS (ESI):589.4[M+H] + .

[0290] Example 214 (3S,5S,8R,9R,10S,14R,17R,18S)-3-carbonylursolic acid-17-methyl-β-D-glucopyranoside (A214) The compound (3S,5S,8R,9R,10S,14R,17R,18S)-28-O-benzyl-3-aldehyde oleanolic acid was replaced with (3S,5S,8R,9R,10S,14R,17R,18S)-17-formylursolic acid. The remaining raw materials, reagents, and production method were the same as in Example 6, and A214 (yield 56%) was obtained. 1H NMR (500 MHz, CDCl3) δ 5.45 (tdd, J = 5.0, 1.8, 1.1 Hz, 1H), 4.85 (d, J = 5.9 Hz, 1H), 4.80 (d, J = 5.7 Hz, 1H), 4.61 (d, J = 6.4 Hz, 1H), 4.23 - 4.17 (m, 1H), 3.96 - 3.88 (m, 1H), 3.84 (dtd, J = 9.3, 7.0, 2.3 Hz, 1H), 3.73 (dddd, J = 8.9, 7.9, 6.3, 2.3 Hz, 1H), 3.70 - 3.62 (m, 2H), 3.62 - 3.51 (m, 2H), 3.31 - 3.23 (m, 1H), 3.00 (d, J = 10.8 Hz, 1H), 2.03 (dd, J = 13.9, 7.0 Hz, 1H), 2.00 - 1.91 (m, 2H), 1.80 - 1.20 (m, 23H), 1.09 (s, 2H), 0.97 (d, J = 1.5 Hz, 3H), 0.95 - 0.86 (m, 14H). LRMS (ESI):589.4[M+H] + .

[0291] Example 215 (3S,5S,8R,9R,10S,13R,14R,17S,18R,19R)-Betulinic acid-17-methyl-β-D-glucopyranoside (A215) The compound (3S,5S,8R,9R,10S,14R,17R,18S)-28-O-benzyl-3-aldehyde oleanolic acid was replaced with (3S,5S,8R,9R,10S,14R,17R,18S)-17-formyl betulinic acid. The remaining raw materials, reagents, and production method were the same as in Example 6, and A215 (yield 48%) was obtained. 1H NMR (500 MHz, CDCl3) δ 4.85 (d, J = 5.9 Hz, 1H), 4.83 - 4.78 (m, 2H), 4.65 (h, J = 1.5 Hz, 1H), 4.61 (d, J = 6.4 Hz, 1H), 4.23 - 4.16 (m, 1H), 3.88 (dddd, J = 32.6, 9.0, 7.5, 2.1 Hz, 2H), 3.73 (dddd, J = 8.8, 7.7, 6.2, 2.2 Hz, 1H), 3.70 - 3.63 (m, 2H), 3.60 - 3.51 (m, 2H), 3.31 - 3.23 (m, 1H), 3.00 (d, J = 10.8 Hz, 1H), 2.23 (dtq, J = 7.0, 5.3, 1.7 Hz, 1H), 1.96 (dd, J = 13.8, 7.2 Hz, 1H), 1.76 - 1.33 (m, 24H), 1.31 (ddq, J = LRMS (ESI):589.4[M+H] + .

[0292] Example 216 (3R,5S,8R,9R,10S,14R,17R,18S)-oleanolic acid 28-β-D-glucopyranoside (A216) The compound (3S,5S,8R,9R,10S,14R,17R,18S)-28-O-benzyl-3-aldehyde oleanolic acid was replaced with (3R,5S,8R,9R,10S,14R,17R,18S)-17-formyl oleanolic acid. The remaining raw materials, reagents, and production method were the same as in Example 10, and A216 (yield 55%) was obtained. 1H NMR (500 MHz, CDCl3) δ 5.48 (d, J = 5.9 Hz, 1H), 5.33 (tdd, J = 5.1, 1.8, 1.1 Hz, 1H), 5.07 (d, J = 5.7 Hz, 1H), 4.57 (d, J = 6.2 Hz, 1H), 4.44 (dd, J = 8.8, 2.6 Hz, 1H), 4.19 (t, J = 4.5 Hz, 1H), 3.67 (ddd, J = 10.9, 3.9, 2.8 Hz, 1H), 3.67 - 3.61 (m, 1H), 3.64 - 3.49 (m, 3H), 3.36 - 3.25 (m, 2H), 3.00 (d, J = 10.8 Hz, 1H), 2.17 (tq, J = 5.1, 1.0 Hz, 1H), 2.05 (dddd, J = 12.5, 6.2, 5.1, 1.0 Hz, 1H), 1.96 - 1.79 (m, 3H), 1.79 - 1.40 (m, 15H), 1.43 - 1.27 (m, 4H), 1.15 (s, 2H), 0.99 - 0.88 (m, 17H). LRMS (ESI):603.4[M+H] + .

[0293] Example 217 (3R,5S,8R,9R,10S,14R,17R,18S)-Oleanolic acid-17-(1'R)-(hydroxy)methyl-β-D-glucopyranoside (A217) The compound (3S,5S,8R,9R,10S,14R,17R,18S)-28-O-benzyl-3-aldehyde oleanolic acid was changed to (3R,5S,8R,9R,10S,14R,17R,18S)-17-formyl oleanolic acid. The remaining raw materials, reagents, and production method were the same as in Example 2, and A217 (yield 55%) was obtained. 1H NMR (500 MHz, CDCl3) δ 5.24 (tdd, J = 5.1, 1.8, 1.0 Hz, 1H), 4.95 (d, J = 5.2 Hz, 1H), 4.82 (d, J = 5.9 Hz, 1H), 4.71 (d, J = 5.7 Hz, 1H), 4.61 (d, J = 6.2 Hz, 1H), 4.20 (t, J = 4.5 Hz, 1H), 3.98 - 3.88 (m, 2H), 3.76 - 3.55 (m, 6H), 3.29 (ddd, J = 10.8, 7.4, 4.7 Hz, 1H), 3.00 (d, J = 10.8 Hz, 1H), 2.23 (tq, J = 4.6, 1.1 Hz, 1H), 1.95 - 1.81 (m, 2H), 1.80 - 1.74 (m, 1H), 1.77 - 1.72 (m, 1H), 1.74 - 1.67 (m, 2H), 1.70 - 1.61 (m, 1H), 1.63 - 1.55 (m, 1H), 1.58 - 1.52 (m, 2H), 1.55 - 1.49 (m, 2H), 1.50 (dd, J = 5.3, 1.6 Hz, 2H), 1.49 - 1.44 (m, 3H), 1.47 - 1.40 (m, 1H), 1.44 - 1.26 (m, 4H), 1.10 (s, 2H), 0.99 - 0.88 (m, 17H). LRMS (ESI):605.4[M+H] +

[0294] Example 218 (3R,5S,8R,9R,10S,14R,17R,18S)-Ursolic acid-17-(1'R)-(hydroxy)methyl-β-D-glucopyranoside (A218) The compound (3S,5S,8R,9R,10S,14R,17R,18S)-28-O-benzyl-3-aldehyde oleanolic acid was changed to (3R,5S,8R,9R,10S,14R,17R,18S)-17-formyl oleanolic acid. The remaining raw materials, reagents, and production method were the same as in Example 2, and A218 (yield 56%) was obtained. 1H NMR (500 MHz, CDCl3) δ 5.47 (tdd, J = 4.9, 1.7, 1.0 Hz, 1H), 4.95 (d, J = 5.3 Hz, 1H), 4.81 (dd, J = 11.0, 5.7 Hz, 2H), 4.61 (d, J = 6.2 Hz, 1H), 4.20 (t, J = 4.5 Hz, 1H), 3.96 (ddd, J = 10.2, 5.1, 2.3 Hz, 1H), 3.94 - 3.87 (m, 1H), 3.76 - 3.50 (m, 7H), 3.29 (ddd, J = 10.8, 7.4, 4.7Hz, 1H), 3.00 (d, J = 10.8 Hz, 1H), 2.06 - 1.24 (m, 25H), 1.09 (s, 2H), 0.97 (d, J = 1.5 Hz, 3H), 0.95 (d, J = 1.5 Hz, 3H), 0.93 (d, J = 1.5 Hz, 3H), 0.93 - 0.89 (m, 10H). LRMS (ESI):605.4[M+H] +

[0295] Example 219 (3R,5S,8R,9R,10S,14R,17R,18S)-Ursolic acid-28-β-D-glucopyranoside (A219) The compound (3S,5S,8R,9R,10S,14R,17R,18S)-28-O-benzyl-3-aldehyde oleanolic acid was replaced with (3R,5S,8R,9R,10S,14R,17R,18S)-17-formylursolic acid. The remaining raw materials, reagents, and production method were the same as in Example 10, and A219 (yield 56%) was obtained. 1H NMR (500 MHz, CDCl3) δ 5.53 - 5.46 (m, 2H), 5.07 (d, J = 5.7 Hz, 1H), 4.57 (d, J = 6.3 Hz, 1H), 4.51 (dd, J = 8.8, 2.6 Hz, 1H), 4.19 (t, J = 4.5 Hz, 1H), 3.71 - 3.58 (m, 3H), 3.58 (dt, J = 7.7, 3.5 Hz, 1H), 3.58 - 3.49 (m, 1H), 3.36 - 3.25 (m, 2H), 3.00 (d, J = 10.8 Hz, 1H), 2.28 - 2.22 (m, 1H), 2.01 - 1.93 (m, 1H), 1.89 - 1.24 (m, 21H), 1.20 (s, 2H), 0.99 - 0.93 (m, 4H), 0.96 - 0.90 (m, 8H), 0.91 (s, 2H), 0.91 (d, J = 5.7 Hz, 1H), 0.90 (d, J = 1.5 Hz, 2H). LRMS (ESI):603.4[M+H] +

[0296] Example 220 (5S,8R,9R,10S,14R,17R,18S)-3-carbonyloleanolic acid-28-6"-O-methyl-β-D-glucuronopyranoside 2,3,4,6-O-tetrabenzyl-1-(pyridin-1-yl)sulfonyl-β-D-thioglucopyranoside was replaced with 2,3,4-O-tribenzyl-1-(pyridin-1-yl)sulfonyl-6-methoxy-β-D-thioglucuronopyranoside. The compound (3S,5S,8R,9R,10S,14R,17R,18S)-28-O-benzyl-3-aldehyde oleanolic acid was replaced with (5S,8R,9R,10S,14R,17R,18S)-3-carbonyl-17-formyl oleanolic acid. The remaining raw materials, reagents, and preparation method were the same as in Example 10, and A220 (yield 58%) was obtained. 1H NMR (500 MHz, CDCl3) δ 5.42 (d, J = 5.8 Hz, 1H), 5.33 (tdd, J = 5.1, 1.8, 1.1 Hz, 1H), 4.89 (d, J = 6.4 Hz, 1H), 4.77 (d, J = 6.3 Hz, 1H), 4.50 (dd, J = 8.7, 2.7 Hz, 1H), 4.39 (d, J = 7.9 Hz, 1H), 3.89 - 3.80 (m, 1H), 3.73 (s, 2H), 3.71 - 3.57 (m, 2H), 2.48 (ddd, J = 12.4, 6.5, 4.0 Hz, 1H), 2.40 (ddd, J = 12.5, 6.6, 4.0 Hz, 1H), 2.17 (tq, J = 5.1, 1.0 Hz, 1H), 2.04 (dddd, J = 12.7, 6.4, 5.1, 1.0 Hz, 1H), 1.95 - 1.87 (m, 1H), 1.91 - 1.83 (m, 1H), 1.83 (dtt, J = 7.1, 2.7, 1.5 Hz, 2H), 1.83 - 1.78 (m, 1H), 1.72 - 1.65 (m, 2H), 1.65 (d, J = 1.6 Hz, 1H), 1.66 - 1.62 (m, 1H), 1.65 - 1.61 (m, 1H), 1.64 - 1.52 (m, 3H), 1.55 - 1.48 (m, 1H), 1.51 - 1.29 (m, 5H), 1.15 (s, 2H), 1.08 (t, J = 1.6 Hz, 5H), 0.97 (d, J = 1.5 Hz, 3H), 0.95 - 0.90 (m, 8H). LRMS (ESI):629.4[M+H] + .

[0297] Example 221 (5S, 8R, 9R, 10S, 14R, 17R, 18S)-3-カルボニルオレアノール acid-28-6''-O-エチル-β-D-グルクロノピラノシド(A221) 2,3,4,6-O-tetrabenzyl-1-(pyridin-1-yl)sulfonyl-β-D-thioglucopyranoside was replaced with 2,3,4-O-tribenzyl-1-(pyridin-1-yl)sulfonyl-6-ethoxy-β-D-thioglucuronopyranoside. The compound (3S,5S,8R,9R,10S,14R,17R,18S)-28-O-benzyl-3-aldehyde oleanolic acid was replaced with (5S,8R,9R,10S,14R,17R,18S)-3-carbonyl-17-formyl oleanolic acid. The remaining raw materials, reagents, and preparation method were the same as in Example 10, and A221 (yield 53%) was obtained. 1 H NMR (500 MHz, CDCl3) δ 5.42 (d, J = 5.8 Hz, 1H), 5.33 (tdd, J = 5.1, 1.8, 1.1 Hz, 1H), 4.95 (d, J = 6.4 Hz, 1H), 4.77 (d, J = 6.3 Hz, 1H), 4.51 (dd, J = 8.7, 2.7 Hz, 1H), 4.45 (d, J = 8.2 Hz, 1H), 4.21 (qd, J = 6.3, 2.5 Hz, 2H), 3.85 (tdd, J = 8.3, 6.4, 1.9 Hz, 1H), 3.71 - 3.57 (m, 2H), 2.48 (ddd, J = 12.5, 6.5, 4.0 Hz, 1H), 2.40 (ddd, J = 12.5, 6.6, 4.0 Hz, 1H), 2.17 (tq, J = 5.1, 1.0 Hz, 1H), 2.04 (dddd, J = 12.6, 6.4, 5.1, 1.0 Hz, 1H), 1.95 - 1.87 (m, 1H), 1.91 - 1.83 (m, 1H), 1.86 - 1.80 (m, 2H), 1.83 - 1.78 (m, 1H), 1.72 - 1.29 (m, 14H), 1.22 - 1.13 (m, 5H), 1.08 (t, J = 1.6 Hz, 5H), 0.99 - 0.92 (m, 6H), 0.93 (d, J = 6.6 Hz, 5H). LRMS (ESI):643.4[M+H] + .

[0298] Example 222 (5S,8R,9R,10S,14R,17R,18S)-3-carbonyloleanolic acid-28-6"-O-2""-fluoroethyl-β-D-glucuronopyranoside (A222) 2,3,4,6-O-tetrabenzyl-1-(pyridin-1-yl)sulfonyl-β-D-thioglucopyranoside was replaced with 2,3,4-O-tribenzyl-1-(pyridin-1-yl)sulfonyl-6-2-fluoroethyl-β-D-thioglucuronopyranoside. The compound (3S,5S,8R,9R,10S,14R,17R,18S)-28-O-benzyl-3-aldehyde oleanolic acid was replaced with (5S,8R,9R,10S,14R,17R,18S)-3-carbonyl-17-formyl oleanolic acid. The remaining raw materials, reagents, and preparation method were the same as in Example 10, and A222 (yield 53%) was obtained. 1H NMR (500 MHz, CDCl3) δ 6.11 (s, 1H), 6.02 (s, 1H), 5.42 (d, J = 5.8 Hz, 1H), 5.33 (tdd, J = 5.1, 1.8, 1.1 Hz, 1H), 4.95 (d, J = 6.3 Hz, 1H), 4.77 (d, J = 6.2 Hz, 1H), 4.51 (dd, J = 8.7, 2.7 Hz, 1H), 3.93 (d, J = 8.2 Hz, 1H), 3.85 (tdd, J = 8.3, 6.3, 1.9 Hz, 1H), 3.71 - 3.57 (m, 2H), 2.48 (ddd, J = 12.5, 6.5, 4.0 Hz, 1H), 2.40 (ddd, J = 12.5, 6.6, 4.0 Hz, 1H), 2.17 (tq, J = 5.1, 1.0 Hz, 1H), 2.04 (dddd, J = 12.6, 6.4, 5.1, 1.0 Hz, 1H), 1.95 - 1.87 (m, 1H), 1.91 - 1.84 (m, 1H), 1.86 - 1.81 (m, 1H), 1.84 - 1.78 (m, 2H), 1.72 - 1.66 (m, 1H), 1.69 - 1.63 (m, 2H), 1.66 - 1.62 (m, 1H), 1.65 - 1.58 (m, 2H), 1.62 - 1.51 (m, 2H), 1.54 - 1.47 (m, 1H), 1.50 - 1.41 (m, 1H), 1.44 - 1.36 (m, 2H), 1.36 (ddd, J = 6.4, 3.4, 1.6 Hz, 1H), 1.36 - 1.29 (m, 1H), 1.15 (s, 2H), 1.08 (t, J = 1.6 Hz, 5H), 0.97 (d, J = 1.5 Hz, 3H), 0.95 - 0.90 (m, 8H). LRMS (ESI):647.4[M+H] + 。

[0299] Example 223 (5S,8R,9R,10S,14R,17R,18S)-3-carbonyloleanolic acid-17-(1'R)-(hydroxy)methyl-6''-O-methyl-β-D-glucuronopyranoside (A223) 2,3,4,6-O-tetrabenzyl-1-(pyridin-1-yl)sulfonyl-β-D-thioglucopyranoside was replaced with 2,3,4-O-tribenzyl-1-(pyridin-1-yl)sulfonyl-6-methoxy-β-D-thioglucuronopyranoside. The compound (3S,5S,8R,9R,10S,14R,17R,18S)-28-O-benzyl-3-aldehyde oleanolic acid was replaced with (5S,8R,9R,10S,14R,17R,18S)-3-carbonyl-17-formyl oleanolic acid. The remaining raw materials, reagents, and preparation method were the same as in Example 2, and A223 (yield 58%) was obtained. 1H NMR (500 MHz, CDCl3) δ 5.24 (tdd, J = 5.1, 1.8, 1.0 Hz, 1H), 4.99 (d, J = 5.3 Hz, 1H), 4.87 (d, J = 6.4 Hz, 1H), 4.75 (d, J = 5.7 Hz, 1H), 4.62 (d, J = 6.1 Hz, 1H), 4.09 (d, J = 7.5 Hz, 1H), 3.93 (ddd, J = 7.3, 5.7, 2.5 Hz, 1H), 3.84 (dddd, J = 8.3, 7.5, 6.4, 1.8 Hz, 1H), 3.77 - 3.69 (m, 1H), 3.73 (s, 3H), 3.68 - 3.60 (m, 1H), 3.56 (tdd, J = 8.3, 6.1, 2.6 Hz, 1H), 2.48 (ddd, J = 12.4, 6.5, 4.0 Hz, 1H), 2.40 (ddd, J = 12.5, 6.6, 4.0 Hz, 1H), 2.23 (tq, J = 4.6, 1.1 Hz, 1H), 1.99 (dddd, J = 12.6, 6.4, 5.2, 1.0 Hz, 1H), 1.95 - 1.86 (m, 1H), 1.89 - 1.78 (m, 3H), 1.78 - 1.59 (m, 4H), 1.59 - 1.26 (m, 11H), 1.11 - 1.05 (m, 8H), 0.99 - 0.92 (m, 8H), 0.90 (s, 2H). LRMS (ESI): 631.4[M+H] + .

[0300] Example 224 (5S, 8R, 9R, 10S, 14R, 17R, 18S)-3-カルボニルウルソール acid-28-6''-O-メチル-β-D-グルクロノピラノシド(A224) The compound (3S,5S,8R,9R,10S,14R,17R,18S)-28-O-benzyl-3-aldehyde oleanolic acid was replaced with (5S,8R,9R,10S,14R,17R,18S)-3-carbonyl-17-formylursolic acid. The remaining raw materials, reagents, and preparation method were the same as in Example 10, and A224 (yield 62%) was obtained. 1 H NMR (500 MHz, CDCl3) δ 5.50 (tdd, J = 4.9, 1.8, 0.9 Hz, 1H), 5.42 (d, J = 5.8 Hz, 1H), 4.89 (d, J = 6.4 Hz, 1H), 4.77 (d, J = 6.3 Hz, 1H), 4.55 (dd, J = 8.7, 2.6 Hz, 1H), 4.39 (d, J = 7.9 Hz, 1H), 3.89 - 3.80 (m, 1H), 3.73 (s, 2H), 3.71 - 3.57 (m, 2H), 2.48 (ddd, J = 12.5, 6.5, 4.0Hz, 1H), 2.40 (ddd, J = 12.5, 6.6, 4.0 Hz, 1H), 2.28 - 2.22 (m, 1H), 2.06 - 1.91 (m, 2H), 1.89 - 1.78 (m, 4H), 1.77 (ddd, J = 12.5, 7.7, 5.2 Hz, 1H), 1.73 - 1.57 (m, 5H), 1.60 - 1.55 (m, 1H), 1.57 - 1.51 (m, 1H), 1.47 - 1.39 (m, 2H), 1.40 (td, J = 2.1, 1.1 Hz, 1H), 1.41 - 1.31 (m, 2H), 1.34 - 1.25 (m, 1H), 1.20 (s, 2H), 1.08 (t, J = 1.6 Hz, 5H), 0.99 - 0.90 (m, 9H), 0.91 (d, J = 2.0 Hz, 2H). LRMS (ESI):629.4[M+H] + .

[0301] Example 225 (3S,5S,8R,9R,10S,13R,14R,17S,18R,19R)-Betulinic acid-28-6″-O-methyl-β-D-glucuronopyranoside (A225) The compound (3S,5S,8R,9R,10S,14R,17R,18S)-28-O-benzyl-3-aldehyde oleanolic acid was replaced with (5S,8R,9R,10S,14R,17R,18S)-3-carbonyl-17-formyl betulinic acid. The remaining raw materials, reagents, and preparation method were the same as in Example 10, and A225 (yield 50%) was obtained. 1 H NMR (500 MHz, CDCl3) δ 5.42 (d, J = 5.9 Hz, 1H), 4.89 (d, J = 6.4 Hz, 1H), 4.83 (h, J = 1.4 Hz, 1H), 4.77 (d, J = 6.3 Hz, 1H), 4.67 (h, J = 1.6 Hz, 1H), 4.51 (dd, J = 8.8, 2.6 Hz, 1H), 3.89 - 3.80 (m, 1H), 3.73 (s, 2H), 3.71 - 3.57 (m, 2H), 3.00 (dddt, J = 10.3, 5.0, 3.3, 1.6Hz, 1H), 2.53 - 2.41 LRMS (ESI):629.4[M+H] + .

[0302] Example 226 (5S,8R,9R,10S,14R,17R,18S)-3-carbonylbetulinic acid-17-(1'R)-(hydroxy)methyl-6''-O-methyl-β-D-glucuronopyranoside (A226) 2,3,4,6-O-tetrabenzyl-1-(pyridin-1-yl)sulfonyl-β-D-thioglucopyranoside was replaced with 2,3,4-O-tribenzyl-1-(pyridin-1-yl)sulfonyl-6-methoxy-β-D-thioglucuronopyranoside. The compound (3S,5S,8R,9R,10S,14R,17R,18S)-28-O-benzyl-3-aldehyde oleanolic acid was replaced with (5S,8R,9R,10S,14R,17R,18S)-3-carbonyl-17-formyl betulinic acid. The remaining raw materials, reagents, and preparation method were the same as in Example 2, and A226 (yield 53%) was obtained. 1 H NMR (500 MHz, CDCl3) δ 4.99 (d, J = 5.3 Hz, 1H), 4.87 (d, J = 6.4 Hz, 1H), 4.81 (h, J = 1.4 Hz, 1H), 4.69 (d, J = 5.3 Hz, 1H), 4.67 - 4.60 (m, 2H), 4.09 (d, J = 7.5 Hz, 1H), 3.91 - 3.80 (m, 2H), 3.75 - 3.66 (m, 3H), 3.66 - 3.52 (m, 2H), 2.53 - 2.41 (m, 2H), 2.13 (dddd, J = 10.4, 5.5, 3.5, 1.7Hz, 1H), 1.83 (ddd, J = 5.7, 2.8, 1.4 Hz, 1H), 1.83 - 1.76 (m, 1H), 1.73 (q, J = 1.4 Hz, 3H), 1.63 - 1.28 (m, 20H), 1.13 - 1.05 (m, 7H), 0.97 (d, J = 1.5 Hz, 3H), 0.92 (d, J = 1.5 Hz, 3H), 0.85 (t, J = 1.4 Hz, 3H). LRMS (ESI):631.4[M+H] + .

[0303] Example 227 (5S,8R,9R,10S,14R,17R,18S)-3-carbonylbetulinic acid-17-(1'R)-(hydroxy)methyl-6''-O-methyl-β-D-glucuronopyranoside (A227) 2,3,4,6-O-tetrabenzyl-1-(pyridin-1-yl)sulfonyl-β-D-thioglucopyranoside was replaced with 2,3,4-O-tribenzyl-1-(pyridin-1-yl)sulfonyl-6-isopropoxy-β-D-thioglucuronopyranoside. The compound (3S,5S,8R,9R,10S,14R,17R,18S)-28-O-benzyl-3-aldehyde oleanolic acid was replaced with (5S,8R,9R,10S,14R,17R,18S)-3-carbonyl-17-formyl oleanolic acid. The remaining raw materials, reagents, and preparation method were the same as in Example 10, and A227 (yield 53%) was obtained. 1H NMR (500 MHz, CDCl3) δ 5.42 (d, J = 5.9 Hz, 1H), 5.33 (tdd, J = 5.1, 1.8, 1.1 Hz, 1H), 5.03 (hept, J = 5.8 Hz, 1H), 4.95 (d, J = 6.4 Hz, 1H), 4.77 (d, J = 6.3 Hz, 1H), 4.51 (dd, J = 8.7, 2.6 Hz, 1H), 4.07 (d, J = 7.9 Hz, 1H), 3.86 (tdd, J = 8.3, 6.4, 1.8 Hz, 1H), 3.72 - 3.57 (m, 2H), 2.48 (ddd, J = 12.4, 6.5, 4.0 Hz, 1H), 2.40 (ddd, J = 12.5, 6.6, 4.0 Hz, 1H), 2.17 (tq, J = 5.1, 1.0 Hz, 1H), 2.04 (dddd, J = 12.7, 6.4, 5.1, 1.0 Hz, 1H), 1.95 - 1.87 (m, 1H), 1.91 - 1.83 (m, 1H), 1.83 (dddd, J = 7.0, 2.7, 1.9, 1.1 Hz, 2H), 1.83 - 1.78 (m, 1H), 1.72 - 1.29 (m, 14H), 1.25 (d, J = 5.7 LRMS (ESI):631.4[M+H] + .

[0304] Example 228 (5S, 8R, 9R, 10S, 14R, 17R, 18S)-3-カルボニルオレアノールクロノピラノシド(A228) 2,3,4,6-O-tetrabenzyl-1-(pyridin-1-yl)sulfonyl-β-D-thioglucopyranoside was replaced with 2,3,4-O-tribenzyl-1-(pyridin-1-yl)sulfonyl-6-cyclopropylmethoxy-β-D-thioglucuronopyranoside. The compound (3S,5S,8R,9R,10S,14R,17R,18S)-28-O-benzyl-3-aldehyde oleanolic acid was replaced with (5S,8R,9R,10S,14R,17R,18S)-3-carbonyl-17-formyl oleanolic acid. The remaining raw materials, reagents, and preparation method were the same as in Example 10, and A228 (yield 54%) was obtained. 1H NMR (500 MHz, CDCl3) δ 5.42 (d, J = 5.8 Hz, 1H), 5.33 (tdd, J = 5.1, 1.8, 1.1 Hz, 1H), 4.95 (d, J = 6.4 Hz, 1H), 4.77 (d, J = 6.3 Hz, 1H), 4.51 (dd, J = 8.7, 2.7 Hz, 1H), 4.12 - 4.05 (m, 3H), 3.85 (tdd, J = 8.2, 6.3, 1.8 Hz, 1H), 3.71 - 3.57 (m, 2H), 2.48 (ddd, J = 12.5, 6.5, 4.0 Hz, 1H), 2.40 (ddd, J = 12.5, 6.6, 4.0 Hz, 1H), 2.17 (tq, J = 5.1, 1.0 Hz, 1H), 2.04 (dddd, J = 12.6, 6.4, 5.1, 1.0 Hz, 1H), 1.95 - 1.83 (m, 2H), 1.86 - 1.78 (m, 3H), 1.72 - 1.66 (m, 1H), 1.69 - 1.63 (m, 2H), 1.66 - 1.62 (m, 1H), 1.65 - 1.47 (m, 6H), 1.50 - 1.41 (m, 1H), 1.44 - 1.36 (m, 2H), 1.36 (ddd, J = 6.4, 3.4, 1.6 Hz, 1H), 1.36 - 1.29 (m, 1H), 1.15 (s, 2H), 1.08 (t, J = 1.6 Hz, 5H), 0.97 (d, J = 1.5 Hz, 3H), 0.95 - 0.90 (m, 8H), 0.58 - 0.44 (m, 4H). LRMS (ESI):669.4[M+H] + .

[0305] Example 229 (5S, 8R, 9R, 10S, 14R, 17R, 18S)-3-カルボニルオレアノール acid-28-6''-N-エチル-β-D-グルクロノピラノシド(A229) 2,3,4,6-O-tetrabenzyl-1-(pyridin-1-yl)sulfonyl-β-D-thioglucopyranoside was replaced with 2,3,4-O-tribenzyl-1-(pyridin-1-yl)sulfonyl-6-ethylamino-β-D-thioglucuronopyranoside. The compound (3S,5S,8R,9R,10S,14R,17R,18S)-28-O-benzyl-3-aldehyde oleanolic acid was replaced with (5S,8R,9R,10S,14R,17R,18S)-3-carbonyl-17-formyl oleanolic acid. The remaining raw materials, reagents, and preparation method were the same as in Example 10, and A229 (yield 58%) was obtained. 1 H NMR (500 MHz, CDCl3) δ 7.28 (t, J = 3.9 Hz, 1H), 5.46 - 5.39 (m, 1H), 5.33 (tdd, J = 5.1, 1.8, 1.1 Hz, 1H), 4.89 (d, J = 6.1 Hz, 1H), 4.78 - 4.71 (m, 1H), 4.50 - 4.43 (m, 1H), 4.09 (d, J = 7.5 Hz, 1H), 3.81 - 3.72 (m, 1H), 3.68 - 3.57 (m, 2H), 3.23 (qd, J = 6.2, 3.9 Hz, 2H), 2.48 (ddd, J = 12.5, 6.5, 4.0 Hz, 1H), 2.40 (ddd, J = 12.5, 6.6, 4.0 Hz, 1H), 2.17 (tq, J = 5.1, 1.0 Hz, 1H), 2.04 (dddd, J = 12.6, 6.4, 5.1, 1.0 Hz, 1H), 1.95 - 1.84 (m, 2H), 1.86 - 1.81 (m, 1H), 1.84 - 1.78 (m, 2H), 1.72 - 1.29 (m, 14H), 1.21 - 1.13 (m, 5H), 1.08 (t, J = 1.6 Hz, 6H), 0.99 - 0.92 (m, 6H), 0.93 (d, J = 6.6 Hz, 5H). LRMS (ESI):642.4[M+H] + .

[0306] Example 230 (5S,8R,9R,10S,14R,17R,18S)-3-carbonyloleanolic acid-28-6"-N-2""-fluoroethyl-β-D-glucuronopyranoside (A230) 2,3,4,6-O-tetrabenzyl-1-(pyridin-1-yl)sulfonyl-β-D-thioglucopyranoside was replaced with 2,3,4-O-tribenzyl-1-(pyridin-1-yl)sulfonyl-6-2-fluoroethylamino-β-D-thioglucuronopyranoside. The compound (3S,5S,8R,9R,10S,14R,17R,18S)-28-O-benzyl-3-aldehyde oleanolic acid was replaced with (5S,8R,9R,10S,14R,17R,18S)-3-carbonyl-17-formyl oleanolic acid. The remaining raw materials, reagents, and preparation method were the same as in Example 10, and A230 (yield 51%) was obtained. 1H NMR (500 MHz, CDCl3) δ 7.80 (t, J = 4.9 Hz, 1H), 5.46 - 5.39 (m, 1H), 5.33 (tdd, J = 5.1, 1.8, 1.1 Hz, 1H), 4.89 (d, J = 6.1 Hz, 1H), 4.78 - 4.71 (m, 1H), 4.58 (td, J = 3.4, 2.3 Hz, 1H), 4.53 - 4.43 (m, 2H), 4.05 (d, J = 7.4 Hz, 1H), 3.81 - 3.72 (m, 1H), 3.68 - 3.57 (m, 2H), 3.44 (dtd, J = 4.6, 3.4, 1.2 Hz, 1H), 3.39 (dtd, J = 4.8, 3.4, 1.1 Hz, 1H), 2.48 (ddd, J = 12.5, 6.5, 4.0 Hz, 1H), 2.40 (ddd, J = 12.5, 6.6, 4.0 Hz, 1H), 2.17 (tq, J = 5.1, 1.0 Hz, 1H), 2.04 (dddd, J = 12.6, 6.4, 5.1, 1.0 Hz, 1H), 1.95 - 1.87 (m, 1H), 1.91 - 1.84 (m, 1H), 1.86 - 1.81 (m, 1H), 1.84 - 1.78 LRMS (ESI):650.4[M+H] + .

[0307] Examples of pharmacological activity tests Example 1: Determination of the in vivo hypoglycemic pharmacodynamic activity of compounds of the present invention 1. Oral glucose tolerance efficacy test of the compound in ICR mice

[0308] 1. Experimental Materials [Table 2]

[0309] After arriving at the Yakulte facility, the animals were housed in a strictly environmentally controlled animal room, with the temperature maintained at 20-24°C and humidity at 30-70%. The temperature and humidity of the room were monitored in real time using a thermo-hygrometer, and the temperature and humidity were recorded twice daily (once in the morning and once in the afternoon). The lighting in the animal room was controlled by an electronic timing system, with 12 hours of light and 12 hours of darkness each day (lights on at 7:00 AM, lights off at 7:00 PM). During the experiment, animals were housed in individual cages, with each mouse provided with a toy. During the experiment, animals had free access to food (large mouse growth / breeding chow) and water. After the animals arrive, they are allowed to adapt to the environment for 1-2 weeks before experiments can begin.

[0310] 2. Drug Preparation and Administration [Table 3] 1) Preparation of drug solutions: Each compound was prepared on the first day of the experiment so that it could be easily used the next day, and then stored in a refrigerator at 4°C. 2) Administration: After grouping, the animals in each group were administered with the drug 0.5 h before receiving sugar.

[0311] 3) Oral glucose tolerance test: 0.5 hours after the end of drug administration, the animals were intragastrically administered glucose. The glucose administration time was set to 0 minutes, and the oral glucose administration amount was 5g / kg, 10ml / kg. The blood glucose levels of the animals were measured before drug administration, before glucose administration, and 15, 30, 60, 90, and 120 minutes after glucose administration. The blood glucose levels were measured using a blood glucose meter and its attached blood glucose test strips.

[0312] 3. Experimental Results The results showed that oral administration of pentacyclic triterpenoid C-glycosides could effectively lower postprandial blood glucose levels in ICR mice (Figure 1). Among them, A25 and A43 had the best hypoglycemic activity, with a relatively significant hypoglycemic effect at a dose of 25 mg / kg, and the hypoglycemic effect was further enhanced at 50 mg / kg (Figure 2).

[0313] Example 2: Measurement of in vitro GLP-1 secretion promoting activity of compounds of the present invention 1. Experimental Materials Cell line: Intestinal endocrine cell line STC-1 cells Negative control: DMSO Positive control: INT777 (TGR5 receptor agonist) Detection tool: HTRF kit Others: KRBH buffer, BSA, DPP4 inhibitor

[0314] 2. Experimental Method STC-1 cells were plated at a predetermined density. After overnight cell adhesion, they were starved with KRBH buffer, maintained with BSA, and treated with a DPP4 inhibitor to reduce GLP-1 degradation. After 1 h, the buffer was switched to KRBH buffer with or without glucose to stimulate GLP-1 secretion. After 1 h of treatment, the supernatants were collected and the GLP-1 concentration was measured using an HTRF kit. The toxicity of the compounds, which are indicators of LDH secretion, was also measured.

[0315] 3. Experimental Results The experimental results showed that A64 has a good in vitro GLP-1 secretion-promoting effect, and its in vitro EC 50 was 7.231 μM, and the positive compound INT777 (EC 50 = 22.82 μM) (Figure 3).

[0316] Example 3: Measurement of the in vitro anti-influenza virus pharmacological activity of the compounds of the present invention 1. Experimental Materials Cell lines: MDCK cells Negative control: DMSO Positive control: Zanamivir / Oseltamivir(50μM) CellTiter-GloR Luminescent Cell Viability Assay Preparation of compound mother solution: Compounds 1 to 7 were diluted to 10 mM / L to give a screening concentration of 50 μM.

[0317] 2. Experimental Method MDCK cells were cultured in a 96-well plate (1 × 10 4 / well) and 37 o C, Drugs were added after 24 h of culture in a 5% CO2 incubator. After adding the drug, the 96-well plate was placed in a 37°C, 5% CO2 incubator and cultured for 36 hours, followed by detection using a microplate reader.

[0318] 3. Experimental Results Inhibition rate calculation formula: I (inhibition rate) = [1-(Xi-Xj) / (Yi-Yj)] x 100% Xi: Number of surviving cells in the test group without virus addition; Xj: Number of surviving cells in the test group with virus addition Yi: Number of surviving cells in the DMSO group without virus addition; Yj: Number of surviving cells in the DMSO group with virus addition As a result, it was revealed that pentacyclic triterpenoid C-glycosides can exhibit effective pharmacological activity against influenza viruses. Among them, A2 showed a virus inhibition rate equivalent to that of the positive drug zanamivir and low cytotoxicity, and its virus inhibition rate was similar to that of the positive drug ribavirin, but its cytotoxicity was lower than that of ribavirin (Figure 4).

[0319] Example 4. Determination of the affinity of compounds of the present invention to coronavirus N protein in vitro 1. Experimental Materials N protein dilution solution: 20 μg / mL Buffer: 10 mM HEPES, pH 7.4, 150 mM NaCl, 3.0 mM EDTA, and 0.005% (v / v) surfactant P20, 5% DMSO. Equipment: Biacore 8K (GE Healthcare)

[0320] 2. Test Method The affinity of compounds for N protein was measured by surface plasmon resonance (SPR) using a Biacore 8K (GE Healthcare). At 25°C, N protein was first diluted to 20 μg / mL. Full-length N protein was then coupled to a CM5 chip using standard amino acid coupling techniques, resulting in a signal value of 10,000 signal units (RU). The running buffer used was 10 mM HEPES, pH 7.4, 150 mM NaCl, 3.0 mM EDTA, 0.005% (v / v) surfactant P20, and 5% DMSO. A 10 mM DMSO stock solution of test compound was diluted with running buffer to seven gradient concentrations (1.56 μM to 100 μM). During testing, the instrument was initialized three times with running buffer, and then test compounds were injected and run sequentially through the chip, with a 100-second binding / dissociation time. After each cycle, the remaining compound on the chip was washed with 50% DMSO before proceeding to the next cycle. Finally, solvent correction was performed using 4.5% to 5.8% running buffer. Based on the generated patterns, solvent correction was performed by subtracting the control values, and the data was used to calculate KD values ​​using the static affinity model and fixed Rmax method using Biacore 8K data processing software.

[0321] 3. Experimental Conclusion The results revealed that pentacyclic triterpenoid C-glycosides exhibited enhanced affinity for N protein, with some compounds exhibiting K values ​​of less than 10 μM (Figures 5 and 6).

[0322] Example 5: Assay of the in vitro anti-SARS-Cov-2 virus pharmacological activity of compounds of the present invention 1. Experimental Materials Vero E6 cells (ATCC-1586) 48-well plate (50,000 cells / well), 96-well plate (20,000 cells / well) 2019-nCoV(nCoV-2019BetaCoV / Wuhan / WIV04 / 2019)

[0323] 2. Experimental Method Vero E6 cells (ATCC-1586) were seeded in a 48-well plate (50,000 cells / well) and culture medium containing gradient concentrations of compounds was added at 100 μL per well. Then, 2019-nCoV (nCoV-2019BetaCoV / Wuhan / WIV04 / 2019) was added at a multiplicity of infection (MOI) of 0.05. After 1 hour of incubation, the supernatant was aspirated, washed, and 200 μL of culture medium containing gradient concentrations of compounds was added again at 200 μL per well. The cells were then incubated at 37°C for 24 hours. After 24 hours, the cell supernatant was collected, viral RNA was extracted, and the viral copy number in the supernatant was measured using real-time fluorescent quantitative PCR. The compound's inhibitory rate was calculated from the viral copy number, and the EC value of the compound was calculated using Prism 6.0. 50 was calculated. Vero E6 cells (ATCC-1586) were seeded in a 96-well plate (20,000 cells / well), and 100 μL of medium containing gradient concentrations of compounds was added per well. After 24 hours, the effects of the compounds on cellular activity were detected using a CCK8 detection kit, and the CC of the compounds was detected using Prism 6.0. 50 was calculated.

[0324] 3. Experimental Conclusion The results showed that pentacyclic triterpenoid C-glycosides could effectively inhibit SARS-CoV-2 virus replication, among which the EC of A104 and A114 50 The inhibitory rates were 3.6 μM and 4.6 μM, and some compounds reached 100% inhibition at the 10 μM level (FIGS. 7 and 8).

[0325] Example 6: Determination of PK properties in mice using compounds of the present invention 1. Experimental Materials animal Species / strain: ICR (CD-1) mouse Gender / number of mice: Male (n=6) Weight (g): Male (20-24g) Diet type: Standard rodent diet water optional A 12-hour fast was initiated before drug administration, and the fast was maintained for 2 hours. Housing: Animal room environment controlled (target conditions: temperature 18-29°C, relative humidity 30-70%. Temperature and relative humidity are monitored daily. An electronic time-controlled lighting system is used to provide a 12-hour light / 12-hour dark cycle).

[0326] 2. Testing method: The dosages are as shown in the following table. [Table 4]

[0327] 3. Experimental Conclusion As a result, the pentacyclic triterpenoid C-glycosides of the present invention have good pharmacokinetic properties, and specific conclusions are shown in Figures 9 and 10. Figure 9 shows that the compounds of the present invention can achieve the required drug exposure within the experimental time frame by both oral and enteral administration. Figure 10 shows that the compounds of the present invention are rapidly released within 8 hours after administration and completely released within 24 hours.

[0328] All documents mentioned in this application are incorporated by reference in this application to the same extent as if each document was individually incorporated by reference. It should be noted that those skilled in the art, after reading the above content of the present invention, may make various changes and modifications to the present invention, and equivalent forms thereof should also be included in the scope defined by the claims appended hereto.

Claims

1. A pentacyclic triterpene C-glycoside derivative compound having a structure represented by the following general formula I, or its racemate, R-isomer, S-isomer, pharmaceutically acceptable salt, or mixture thereof: 【Chemistry 1】 During the ceremony, Ring A is selected from the group consisting of a 6-membered saturated or unsaturated carbocyclic ring; R １ , R ２ and R ３ are each independently selected from the group consisting of hydrogen and methyl; R ４ is selected from the group consisting of hydrogen, isopropenyl; R ５ is hydrogen, deuterium, tritium, halogen, cyano, amino, nitro, hydroxyl, sulfhydryl, aldehyde group, carboxyl, sulfonyl, phosphate group, substituted or unsubstituted C １ ~C ６ Alkyl, substituted or unsubstituted C １ ~C ６ Alkoxy, substituted or unsubstituted C ６ ~C １０ aryl, a substituted or unsubstituted 5- to 7-membered heterocycle having 1 to 3 heteroatoms selected from oxygen, sulfur, and nitrogen; a substituted or unsubstituted C １ ~C ６ Alkyl-phenyl, substituted or unsubstituted C ３ ~C １２ Cycloalkyl, substituted or unsubstituted C ２ ~C １０ Acyl, substituted or unsubstituted C ２ ~C １０ Ester group, substituted or unsubstituted C ６ ~C １０ aryloxy, substituted or unsubstituted C １ ~C ６ Amide, or Y-R ７ is selected from the group consisting of Y is -(CH ２ ) ｍ CHR ９ selected from the group consisting of -, carbonyl, -CONH, and COO-; where m is 0 or 1; R ７ is hydrogen, substituted or unsubstituted C １ ~C ６ Alkyl, substituted or unsubstituted C ２ ~C ６ alkenyl, a substituted or unsubstituted 5- to 7-membered heterocycle having 1 to 3 heteroatoms selected from oxygen, sulfur, and nitrogen, a substituted or unsubstituted C ２ ~C １０ Ester group, substituted or unsubstituted C ５ ~C ９ Furanosyl, substituted or unsubstituted C ５ ~C ９ pyranosyl; Z is carbonyl, CH(R ９ ) ２ , C=N-R ８ , C═N—NH—R ８ , or -X-R ６ is selected from the group consisting of R ８ is selected from the group consisting of hydrogen, deuterium, tritium, halogen, cyano, amino, nitro, hydroxy, sulfhydryl, an aldehyde group, carboxy, sulfonyl, substituted or unsubstituted C1-C6 alkyl, substituted or unsubstituted C1-C6 alkoxy, substituted or unsubstituted C6-C10 aryl, a substituted or unsubstituted 5-7 membered heterocycle having 1 to 3 heteroatoms selected from oxygen, sulfur and nitrogen, substituted or unsubstituted C1-C6 alkyl-phenyl, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted C2-C10 acyl, a substituted or unsubstituted C2-C10 ester group, substituted or unsubstituted C6-C10 aryloxy, and substituted or unsubstituted C1-C6 amide; R ９ is selected from the group consisting of hydrogen, deuterium, tritium, halogen, cyano, amino, nitro, hydroxy, and sulfhydryl; R ６ is hydrogen, substituted or unsubstituted C １ ~C ６ Alkyl, substituted or unsubstituted C ２ ~C ６ a substituted or unsubstituted 5- to 7-membered heterocyclic ring having 1 to 3 heteroatoms selected from alkenyl, oxygen, sulfur, and nitrogen; a substituted or unsubstituted C ５ ~C ９ Furanosyl, substituted or unsubstituted C ５ ~C ９ pyranosyl, wherein the substitution means that one or more hydrogens or hydroxyls on the sugar ring are replaced with hydrogen, deuterium, tritium, halogen, cyano, amino, nitro, sulfhydryl, aldehyde group, carboxy, benzyl, substituted or unsubstituted C １ ~C １２ Alkoxycarbonyl, substituted or unsubstituted C ２ ~C １２ alkylaminocarbonyl, substituted or unsubstituted C ２ ~C １０ Acyl, sulfonyl, phosphoryl, C ５ ~C ９ Furanosyl, C ５ ~C ９ pyranosyl; X is -CHR ９ -, carbonyl, S, -NHC(O)-R ８ , -NHS(O) ２ -R ８ , -NHC(O)NH-R ８ , -NHC(S)NH-R ８ , -COO-, -OS(O) ２ -R ８ is selected from the group consisting of n is 1 or 2; Unless otherwise specified, in the above formula, the substitution means that a hydrogen atom on the corresponding group or a hydroxy on the sugar ring is replaced with deuterium, tritium, halogen, hydroxy, carboxy, sulfhydryl, benzyl, C １ ~C １２ Alkoxycarbonyl, C １ ~C ６ Aldehyde group, amino, C １ ~C ６ Amido, nitro, cyano, unsubstituted or halogenated C １ ~C ６ Alkyl, C ２ ~C １０ Alkenyl, C １ ~C ６ Alkoxy, C １ ~C ６ Alkyl-amine group, C ６ ~C １０ Aryl, 5- or 6-membered heteroaryl, 5- or 6-membered non-aromatic heterocyclic group, —O—(C ６ ~C １０ aryl), —O—(5- or 6-membered heteroaryl), C １ ~C １２ alkylaminocarbonyl, substituted or unsubstituted C ２ ~C １０ Acyl, sulfonyl (-SO ２ -OH), phosphoryl (-PO ３ —OH), C ５ ~C ９ Furanosyl, C ５ ~C ９ a pentacyclic triterpene C-glycoside derivative compound having a structure represented by the general formula I, characterized in that it is substituted with one or more substituents selected from the group consisting of pyranosyl, or a racemic mixture, R-isomer, S-isomer, pharmaceutically acceptable salt, or mixture thereof.

2. The compound of formula I has a structure represented by general formula II: 【Chemistry 2】 During the ceremony, R ５ is selected from the group consisting of hydrogen, deuterium, tritium, halogen, cyano, amino, nitro, hydroxy, sulfhydryl, an aldehyde group, carboxy, sulfonyl, a phosphate group, substituted or unsubstituted C1-C6 alkyl, substituted or unsubstituted C1-C6 alkoxy, substituted or unsubstituted C6-C10 aryl, a substituted or unsubstituted 5-7 membered heterocycle having 1 to 3 heteroatoms selected from oxygen, sulfur and nitrogen, substituted or unsubstituted C1-C6 alkyl-phenyl, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted C2-C10 acyl, a substituted or unsubstituted C2-C10 ester group, substituted or unsubstituted C6-C10 aryloxy, and substituted or unsubstituted C1-C6 amide; X is -CHR ９ -, carbonyl; R ６ is selected from the group consisting of substituted or unsubstituted C5 to C9 furanosyl and substituted or unsubstituted C5 to C9 pyranosyl, wherein the substitution means that one or more hydrogens or hydroxyls on the sugar ring are substituted with a substituent selected from the group consisting of hydrogen, deuterium, tritium, halogen, cyano, amino, nitro, sulfhydryl, aldehyde group, carboxy, benzyl, substituted or unsubstituted C1 to C12 alkoxycarbonyl, substituted or unsubstituted C2 to C12 alkylaminocarbonyl, substituted or unsubstituted C2 to C10 acyl, sulfonyl, phosphoryl, C5 to C9 furanosyl, and C5 to C9 pyranosyl; R ９ is selected from the group consisting of hydrogen, deuterium, tritium, halogen, cyano, amino, nitro, hydroxy, and sulfhydryl; Ring A is selected from the group consisting of a 6-membered saturated or unsaturated carbocyclic ring; n is 1 or 2 10. The compound according to claim 1, or its racemate, R-isomer, S-isomer, pharmaceutically acceptable salt, or mixture thereof.

3. The compound of Formula I has a structure represented by the following general formula III: 【Transformation 3】 During the ceremony, R １ , R ２ and R ３ are each independently selected from the group consisting of hydrogen and methyl; R ４ is selected from the group consisting of hydrogen, isopropenyl; R ７ is selected from the group consisting of hydrogen, substituted or unsubstituted C5-C9 furanosyl, and substituted or unsubstituted C5-C9 pyranosyl, and the substitution means that one or more hydrogens or hydroxyls on the sugar ring are replaced with a substituent selected from the group consisting of hydrogen, deuterium, tritium, halogen, cyano, amino, nitro, sulfhydryl, aldehyde group, carboxy, benzyl, substituted or unsubstituted C1-C12 alkoxycarbonyl, substituted or unsubstituted C1-C12 alkylaminocarbonyl, substituted or unsubstituted C2-C10 acyl, sulfonyl, phosphoryl, C5-C9 furanosyl, and C5-C9 pyranosyl; Y is -(CH ２ ) ｍ CHR ９ -, carbonyl; m is 0 or 1, R ９ is selected from the group consisting of hydrogen, deuterium, tritium, halogen, cyano, amino, nitro, hydroxy, and sulfhydryl; Z is carbonyl, CH(R ９ ) ２ , =N-R ８ , and -X-R ６ is selected from the group consisting of R ９ is selected from the group consisting of hydrogen, halogen, cyano, amino, nitro, hydroxy, and sulfhydryl; X is -CHR ９ -, carbonyl, S, -NHC(O)-R ８ , -NHS(O) ２ -R ８ , -NHC(O)NH-R ８ , -NHC(S)NH-R ８ , -COO-, -OS(O) ２ -R ８ is selected from the group consisting of R ６ is hydrogen, substituted or unsubstituted C １ ~C ６ Alkyl, substituted or unsubstituted C ２ ~C ６ a substituted or unsubstituted 5- to 7-membered heterocyclic ring having 1 to 3 heteroatoms selected from alkenyl, oxygen, sulfur, and nitrogen; a substituted or unsubstituted C ５ ~C ９ Furanosyl, substituted or unsubstituted C ５ ~C ９ pyranosyl, wherein the substitution means that one or more hydrogens or hydroxyls on the sugar ring are replaced with hydrogen, deuterium, tritium, halogen, cyano, amino, nitro, sulfhydryl, aldehyde group, carboxy, benzyl, substituted or unsubstituted C １ ~C １２ Alkoxycarbonyl, substituted or unsubstituted C ２ ~C １２ alkylaminocarbonyl, substituted or unsubstituted C ２ ~C １０ Acyl, sulfonyl, phosphoryl, C ５ ~C ９ Furanosyl, C ５ ~C ９ pyranosyl; Ring A is selected from the group consisting of a 6-membered saturated or unsaturated carbocyclic ring; n is 1 or 2 10. The compound according to claim 1, or its racemate, R-isomer, S-isomer, pharmaceutically acceptable salt, or mixture thereof.

4. The compound of claim 1, wherein the compound of Formula I has a structure represented by the following general formula IV, V, or VI: 【Chemistry 4】

5. R ５ is selected from the group consisting of hydrogen, halogen, hydroxy, carboxy, substituted or unsubstituted C1 to C6 alkyl, substituted or unsubstituted C1 to C6 alkoxy, substituted or unsubstituted C2 to C10 acyl, substituted or unsubstituted C2 to C10 ester group, and substituted or unsubstituted C1 to C6 amide.

3. The compound according to claim 2, or its racemate, R-isomer, S-isomer, pharmaceutically acceptable salt, or mixture thereof.

6. R ９ is hydrogen, hydroxy, aldehyde, sulfhydryl or -X-R ６ is selected from the group consisting of X is -CHR ９ -, carbonyl, S, -NHC(O)-R ８ , -NHS(O) ２ -R ８ , -NHC(O)NH-R ８ , -NHC(S)NH-R ８ , -COO-, -OS(O) ２ -R ８ is selected from the group consisting of R ６ is a substituted or unsubstituted C １ ~C ６ Alkyl, substituted or unsubstituted C ２ ~C ６ a substituted or unsubstituted 5- to 7-membered heterocyclic ring having 1 to 3 heteroatoms selected from alkenyl, oxygen, sulfur, and nitrogen; a substituted or unsubstituted C ５ ~C ９ Furanosyl, substituted or unsubstituted C ５ ~C ９ pyranosyl, wherein the substitution means that one or more hydrogens or hydroxyls on the sugar ring are replaced with hydrogen, deuterium, tritium, halogen, cyano, amino, nitro, sulfhydryl, aldehyde group, carboxy, benzyl, substituted or unsubstituted C １ ~C １２ Alkoxycarbonyl, substituted or unsubstituted C ２ ~C １２ alkylaminocarbonyl, substituted or unsubstituted C ２ ~C １０ Acyl, sulfonyl, phosphoryl, C ５ ~C ９ Furanosyl, C ５ ~C ９ pyranosyl 4. The compound according to claim 3, or its racemate, R-isomer, S-isomer, pharmaceutically acceptable salt, or mixture thereof.

7. The compound according to claim 1, wherein the pentacyclic triterpenoid C-glycoside is selected from the following compounds: Table 1-1 Table 1-2 Table 1-3 Table 1-4 Table 1-5 Table 1-6 Table 1-7 Table 1-8 Table 1-9 Table 1-10 Table 1-11 Table 1-12 Table 1-13 Table 1-14 Table 1-15 Table 1-16 Table 1-17 Table 1-18 Table 1-19 Table 1-20 Table 1-21 Table 1-22 Table 1-23 Table 1-24 Table 1-25 Table 1-26 Table 1-27 Table 1-28 Table 1-29 Table 1-30 Table 1-31 Table 1-32 Table 1-33 Table 1-34 Table 1-35 Table 1-36 Table 1-37 Table 1-38 Table 1-39 Table 1-40 Table 1-41

8. A method for producing the compound of claim 1, comprising the steps of: The method for producing the same includes Scheme 1 or Scheme 2, Scheme 1: Starting from a compound of formula IIa, a compound of formula II is prepared through step a and optional step b, c or d, 【Transformation 5】 In the formula, the definitions of each group are as defined in claim 1, Step a: reacting compound IV with compound III to obtain the product of step a; Step b: reducing the product of step a to obtain the product of step b; Step c: alkylating the product of step b to obtain the product of step c; Step d: reacting the product of step c with a Dess-Martin reagent to obtain a compound of formula II; wherein the structure of compound IV is: 【Transformation 6】 Scheme 2: The production method of the above, characterized in that a compound of formula III is produced from a compound of formula IIIa via step a and optional step b, c or d. 【Transformation 7】

9. 1. A pharmaceutical composition comprising:

10. A pharmaceutical composition comprising a therapeutically effective amount of one or more of the compounds of formula I according to claim 1, their pharmaceutically acceptable salts, racemates, R-isomers and S-isomers, and one or more pharmaceutically acceptable carriers, excipients, adjuvants, auxiliary materials and / or diluents.

10. Use of the compound of formula I or II according to claim 1, or a racemate, R-isomer, S-isomer or pharmaceutically acceptable salt thereof, in the manufacture of a medicament for treating or preventing metabolic and viral diseases associated with diabetes, comprising: Preferably, the disease is selected from the group consisting of diabetes, influenza, obesity, liver fibrosis, metabolic diseases, and viral diseases.

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