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Application of an improved fischer-type glycosylation reaction in the construction of glycosidic bonds in saponins

A technology of glycosidic bonds and saponins, which is applied in the field of construction strategies of glycosidic bonds in saponins, can solve the problems of increasing production costs and unfavorable industrial production, and achieve the effect of easy operation, easy industrial production, and simple steps

Inactive Publication Date: 2018-03-23
YANGZHOU BLUE BIOMEDICAL TECH CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] Secondly, since the glycosidation reaction in the synthesis of saponins is the reaction between the active sugar group donor and the hydroxyl group in the aglycone, the prior art requires strict control of water in the reaction system for constructing glycosidic bonds, and generally requires the use of dried Anhydrous solvents are processed, and the reaction system needs to be fed with nitrogen or inert gas, which greatly increases the cost of production and is not conducive to large-scale industrial production

Method used

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  • Application of an improved fischer-type glycosylation reaction in the construction of glycosidic bonds in saponins
  • Application of an improved fischer-type glycosylation reaction in the construction of glycosidic bonds in saponins
  • Application of an improved fischer-type glycosylation reaction in the construction of glycosidic bonds in saponins

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0028] 3-O-β-D-Glucopyranose-DHEA ( )Synthesis

[0029] Weigh dehydroepiandrosterone (34.6g, 0.12mol), D-glucose (18.0g, 0.1mol) was dissolved in anhydrous toluene (200mL), at 80 ° C, add H 2 SO 4 -SiO 2 (250mg, 0.5mmol), react at a constant temperature under the protection of argon until the D-glucose almost completely disappears (about 5h) as detected by TLC. Methane is used as the eluent, and TLC detects until there is no dehydroepiandrosterone in the eluent, and the eluate is concentrated to obtain dehydroepiandrosterone (14.4g, 0.05mol), and ethyl acetate is used as the eluent to continue Elution, TLC detection until there is no title compound in the eluate, the eluate is concentrated to obtain 22.5 g of white solid, which is the title compound, the yield is 50.0%, and the purity by HPLC is about 98.6%.

[0030] Structure confirmation data: ESI-MS (m / z): 473.3[M+Na l + , 1 H NMR (400MHz, CD 3 OD): δ5.42(d, J=5.2Hz, 1H, H-6), 4.83(d, J=1.4Hz, 1H, H-1), 3.75(dd, J=3...

Embodiment 2

[0035] Trillin (trillin, CAS registration number: 14144-06-0, structural formula: )Synthesis

[0036] Weigh diosgenin (62.2g, 0.15mol), D-glucose (18.0g, 0.1mol) was dissolved in THF (300mL), add TfOH-SiO 2 (500mg, 1.0mmol), reflux reaction, until TLC detection D-glucose almost completely disappeared (about 12h), after the reactant was concentrated, through silica gel column chromatography (silica gel 200~300 mesh), first use dichloromethane as washing Remove agent, TLC detects until there is no diosgenin in the eluent, concentrates the eluent to obtain diosgenin (16.6g, 0.04mol), then continues eluting with ethyl acetate as eluent, TLC detects until eluent There was no trillium in the eluate, and the eluate was concentrated to obtain trillium (46.1 g), with a yield of 80% and a purity of 96.5% by HPLC.

[0037] Structure confirmation data: Melting point: 275-280°C, ESI-MS (m / z): 577.5[M+H l + , 1 HNMR (400MHz, CD 3 OD) δ: 0.64 (3H, d, J = 5.1Hz, CH 3 -27),0.78(3H,s,CH ...

Embodiment 3

[0039] 3-O-β-L-arabinopyranose-oleanolic acid benzyl ester ( )Synthesis

[0040] Weigh benzyl oleanolic acid (136.7g, 0.25mol), L-arabinose (15.0g, 0.1mol) was dissolved in dioxane (500mL), at 100 ° C, add HClO 4 -SiO 2 (1.0g, 2.0mmol), constant temperature reaction, until the TLC detection of L-arabinose almost completely disappeared (about 2h), after the reaction was concentrated, silica gel column chromatography (silica gel 200 ~ 300 mesh), first with dichloromethane As eluent, TLC detects until there is no benzyl oleanolic acid in the eluent, and the eluent is concentrated to obtain benzyl oleanolic acid (65.6g, 0.12mol), and ethyl acetate is used as the eluent The eluent was continuously eluted and detected by TLC until there was no title compound in the eluate, and the eluate was concentrated to obtain the title compound (48.9 g), with a yield of 72% and a purity of 97.3% by HPLC.

[0041] Structure confirmation data: ESI-MS (m / z): 701.5[M+Na l + , 1 H NMR (400MHz,...

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Abstract

The invention belongs to the field of organic synthesis, and involves a synthesis method of saponin, and in particular a method to construct glycosidic bond in saponin. The method includes the following steps: directly reacting an excessive amount of aldose or ketose with aglycone in an appropriate organic solvent under the action of an acid catalyst and reflux temperature of 30 DEG C to obtain the target product of saponin.

Description

technical field [0001] The invention belongs to the field of organic synthesis and relates to a construction strategy of glycosidic bonds in saponins. Background technique [0002] Saponins are a special class of secondary metabolites, which are sugar moiety linked with triterpene, steroid or steroid alkaloid through glycosidic bonds. conjugate. According to the structure of saponins, they are divided into triterpenoid saponins, steroidal saponins and steroidal alkaloids. Saponin is a glycoconjugate of triterpenes and steroids that widely exists in nature and has a wide range of activities. Antibacterial, antiviral, hypoglycemic, prevent and treat cardiovascular disease, hypotensive, diuretic, anti-fatigue, antipyretic and analgesic, liver protection, etc., and can also be used as a natural food sweetener, protective agent, foaming agent, and flavor enhancer , antioxidants, etc. However, saponins always exist in a large family with similar structures in nature, which mak...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07J71/00C07J63/00C07J17/00C07J75/00C07H15/256C07H1/00
CPCC07H1/00C07H15/256C07J17/005C07J63/008C07J71/0005
Inventor 于跃陈敏
Owner YANGZHOU BLUE BIOMEDICAL TECH CO LTD
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