Chemical o-glycosylation and glucuronidation of cannabinoids

Abstract

This disclosure presents describes methods for the chemical glycosylation and glucuronidation of cannabinoids. These methods use readily available glycosyl and glucuronyl donors and offer a convenient and versatile approach to access a diverse range of cannabinoid glycosides and glucuronides. Selected compounds have been evaluated for their physicochemical properties and in vitro stability to understand the structure-property relationship and identify their potential applications. The possible uses of these compounds could span various fields, including medicine, consumer goods, and nutrition supplements.

Description

[0001] CHEMICAL O-GLYCOSYLATION AND GLUCURONIDATION OF CANNABINOIDS CROSS-REFERENCE TO RELATED APPLICATIONS This International PCT Application claims the benefit of and priority to U.S. Provisional Application No.63 / 626,997, filed January 30, 2023. The specification, claims, and figures of the above-referenced application is hereby incorporated, in its entirety by reference. TECHNICAL FIELD The present disclosure is generally directed to the synthesis of novel cannabinoid glycosides and cannabinoid glucuronides, and in particular methods for the in vitro chemical synthesis of cannabinoid glycosides and cannabinoid glucuronides. BACKGROUND The Cannabis plant (Cannabis sativa L.), known for its medicinal and recreational uses, has been utilized for thousands of years. Recently, it has attracted considerable attention for its secondary metabolites, thanks to remarkable advancement made in elucidating the structure of these metabolites over several decades. The plant produces more than 600 chemical compounds, which include a diverse set of small molecules such as cannabinoids, flavonoids, stilbenoids, terpenoids, polyketides, oxylipins, and alkaloids (Stasiłowicz et al., Int J Mol 2021, 22, 778). Among these, cannabinoids, a class of mono- to tetracyclic meroterpenoids with 130 members known as phytocannabinoids, are the most important (Lange et al., Phytochem Rev 2922, 21, 1273). These naturally occurring cannabinoids can be classified into 11 subclasses based on their biosynthetic origin and core structures. These include cannabigerol (CBG), cannabichromene (CBC), cannabidiol (CBD), (−)-Δ9-trans-tetrahydrocannabinol (Δ9-THC), (−)-Δ8-trans- tetrahydrocannabinol (Δ8-THC), cannabicyclol (CBL), cannabielsoin (CBE), cannabinol (CBN), cannabinodiol (CBND), cannabitriol (CBT), and other miscellaneous cannabinoids. Over the years, numerous studies have supported the therapeutic potential of these cannabinoids in treating various medical conditions such as pain, anxiety, epilepsy, nausea, vomiting, and post-traumatic stress disorder. Subsequently, the two most abundant cannabinoids in cannabis plants, Δ9-THC and CBD, have been successfully developed into medicines (Banerjee et al., Org Biomol Chem 2023, 21, 3715). For instance, Dronabinol, which contains Δ9-THC formulated in sesame oil, became the first FDA-approved cannabinoid medication for anorexia associated with weight loss in patients with AIDS and nausea and vomiting associated with cancer chemotherapy. Epidiolex®(a pure CBD solution) and Sativex®(a 1:1 CBD and Δ9-THC oromucosal spray) were approved by the US Food and Drug Administration and the European Medicine Agency for two rare, treatment-resistant seizures associated with Lennox Gastaut syndrome (LGS) and Dravet syndrome (DS), and for alleviating neuropathic pain and symptoms of multiple sclerosis. Minor cannabinoids such as CBG, CBN, CBC, CBDA, CBGA, CBDV, THCV, and others have also been the focus of pharmacological studies over the last few decades (Walsh et al., Front. Pharmacol 2021,12:777804). These are currently being investigated in several clinical trials for their potential therapeutic effects related to sleep disorders, obesity, diabetes, anti-inflammatory properties, and beneficial skin properties. Following the 2018 US Farm Bill, which legalized industrial hemp with less than 0.3% Δ9- THC content (dry weight), these hemp-derived cannabinoids have gained significant popularity in recent years. They are used as ingredients in food, beverages, supplements, personal care products, cosmetics, and other consumer products. CBD, in particular, stands out as a consumer favorite and is available in various forms like candies, beverages, baked goods, chocolates, sauces, and savory snacks. As the cannabis consumer market rapidly evolves, there is growing interest in minor cannabinoids such as CBDA, CBC, CBN, and CBG. These compounds are also gaining attention for their potential benefits in pain relief, sleep aids, and skincare, among other areas. Consistent with the current trend, the global market value of CBD-containing products is expected to grow rapidly. A study conducted by BDS Analytics predicts that CBD sales in the U.S. alone will exceed $20 billion by 2024 (Zenone et al., BMC Public Heal 2021, 21, 1285). Edible CBD in food and recreational beverage products has become an increasingly popular route of CBD consumption and represents a fast-growing subsector in the industry. As discussed, CBD and other hemp-derived cannabinoids have a variety of pharmacological and consumer product applications. However, when administered orally, these products not only delay reaching an appropriate concentration in blood and tissue, but also exhibit low and variable oral bioavailability (Bar-Hai et al., Expert Opinion Drug Metab Toxicol 2022, 18 (5), 313; McClements et al., Annu Rev Food Sci Technol 2020, 11, 45). Several factors contribute to these undesired pharmacokinetic behaviors, including poor solubility in an aqueous environment, incomplete gastrointestinal absorption, instability in gastric pH, extensive hepatic metabolism, and drug-drug interactions. The high hydrophobicity and intrinsically low solubility of these cannabinoids are considered the primary factors contributing to their unpredictable oral bioavailability. This necessitates the use of oils and solvents as carriers in product formulations, which are often not well-tolerated and result in poor consumer compliance. Additionally, the highly lipophilic cannabinoids are prone to degradation, especially in solution, because of the effects of light, temperature, and autooxidation. In response to this challenge, research activity has increased dramatically to develop new technologies for improving water solubility. These techniques include crystal engineering, particle size reduction, solid dispersion, carrier systems (such as nanotechnology), and structural modification (such as prodrugs and salt formation) (Bhalani et al., Biomed 2022,10, 2055). Each technology has its own benefits and limitations in enhancing water solubility, and the choice often depends on the specific properties of the molecules and their intended use. However, compared to other pharmaceutical technologies, structural modifications provide a more direct and efficient method to improve the solubility and oral bioavailability of poorly water-soluble molecules. In this context, the structural modification of CBD and other cannabinoids has been successfully demonstrated to improve their solubility by combining prodrug and salt formation strategies (Kim, WO 2023235386 A1, Trait Biosciences). In nature, a crucial process exists for the modification of chemical structures in natural products (e.g., plant), facilitated by tailoring enzymes (Härtl et al., Tailoring Natural Products with Glycosyltransferases. 2017, 219–263). One such pathway is glycosylation, which involves the transfer of sugar units to a natural aglycone and is typically catalyzed by enzymes known as glycosyltransferases (GTs). The addition of a sugar residue significantly enhances water solubility and stability and improves biological and pharmacological properties by reducing toxicity and side effects. As a result, natural glycosides have become attractive target compounds for use in food additives, cosmetics, therapeutics, and nutraceuticals. Today, many glycosides are utilized as therapeutic drugs, functional ingredients, and dietary supplements. Phenolic glycosides, a class of natural glycosides, have gained special attention due to the widespread presence of various phenolic compounds in nature and their promising pharmacological properties, including antitumor, antioxidant, antibacterial, and anti-inflammatory effects (Xu et al., J Carbohydr Chem 2016, 35(1), 1). Despite the importance of phenolic compounds, their application is limited due to their poor solubility and instability in aqueous solutions (Lobiuc et al., Molecules 2023, 28(3), 1114). Therefore, glycosylation of natural phenolic products, including arbutin, caffeic acid, phloretin, resveratrol, catechin, flavonoids, lignans, and curcuminoids, is considered an attractive approach to enhance their properties and functions. Accordingly, the glycosylation of cannabinoids, also known as terpeno-phenol compounds due to their phenolic moiety, has garnered significant attention in the scientific community. This interest has led to the development of various biotechnological glycosylation processes. These advancements have been further propelled by the increasing market demand and therapeutic potential of CBD and other hemp-derived cannabinoids. These processes involve either enzymatic in vitro glycosylation, in vivo glycosylation using fermentation with an external acceptor (e.g., CBD), or de novo biosynthesis from fermentation, which are typically catalyzed by uridine glycosyltransferases (Zipp et al., WO 2017053574 A1, Vitality Biopharma, Inc.; Schuetz et al., WO 2022099078 A1, Willow Biosciences Inc.; Milne et al., WO 2020239784 A1, Octarine Bio Ivs.; Sayre et al., U.S. Patent 20220267820 A1, Trait Biosciences). As a secondary metabolite in the plant tissue of Pinellia ternate, three cannabinoid glycosides, CBD-1'-O-^^-D-glucoside (3), CBD-1',3'-di-O-^^-D-glucoside (8), and CBN-1-O-^^-D-glucoside (13), were also identified by in vitro biotransformation, indicating that these cannabinoid glycosides are naturally occurring products (Tanaka et al., Plant Cell Reports 1996, 15, 819; Tanaka et al., J Nat Prod 1993, 56 (12), 2068). Given the stimulating biological, pharmacological, and physiochemical properties of phenolic glycosides, the chemical glycosylation of natural and non-natural phenolic compounds has been extensively investigated over the past several decades to identify ideal conditions for effective glycosylation (Jacobsson et al., Carbohydr Res 2006, 341, 1266; Yu et al., Acc Chem Res 2012, 45(8), 1227; Yang et al., Nat Prod Rep 2015, 32, 1331; Jensen et al., J Chem Soc, Perkin Trans 1, 2002, 2219; Wadouachi et al., Molecules 2011, 16, 3933). As a result, numerous new synthetic methods have been developed. These mature chemical tools for glycosylation enable the effective isolation of pure glycosides in high yield and can be adapted to optimize the properties, safety, efficacy of natural glycosides through efficient derivatization. However, the chemical synthesis of cannabinoid glycosides has not been as thoroughly explored as other natural and non-natural phenolic glycosides. A reported synthesis involved a mixture of C- and O-glucosides of CBN, ∆8-THC, and ∆9-THC using 2,3,4,6-tetra-O-acetyl-^^-D- glucopyranosyl 2,2,2-trichloroacetimidate as a glucosyl donor and BF3• OEt2as a Lewis acid (Anindya et al., WO 2023053134 A1, Council of Scientific & Industrial Research). However, this synthetic strategy has limitations in its efficiency and broad applicability for synthesis of cannabinoid glycosides. Glucuronidation, similar to glycosylation, is an effective method to increase the aqueous solubility of natural products. Glucuronides, the most important class of phase II metabolites, are generated in vivo through the action of UDP-glucuronosyltransferases. Related to this, a study reported that specific human recombinant UDP-glucuronosyltransferases, which are responsible for the formation of Phase II cannabinoid glucuronide metabolites, have been identified (Mazur et al., Drug Metab Dispos 200937(7), 1496). The glucuronides have the potential to not only enhance pharmacological properties but also facilitate uptake and improve antioxidant properties. Additionally, glucuronide prodrugs can be used effectively to deliver bioactive molecules to their sites of action (Docampo et al., J Agric Food Chem 2017, 65(35), 7607). However, studies on the synthesis of cannabinoid glucuronide are limited. Two groups reported the synthesis of C-glucuronide of ∆8- and ∆9-THC using a glucosyl donor (methyl 1,2,3,4- tetra-O-acetyl-^^-D-glucuronate, 2,3,4-tri-O-acetyl-^^-D-glucuronic acid methyl ester trichloroacetimidate, or acetobromo-^^,^^-D-glucuronic acid methyl ester) in the presence of BF3• OEt2or Hg(CN)2(Yagen et al., J Am Chem Soc 1977, 99(19), 6444; Zehavi et al., Carbohydr Res 1981, 98(1), 143; Baek et al., Bull Korean Chem Soc 1991, 12(6), 604). However, these methods have proven synthetically unproductive due to low yield and have not been applied for the synthesis of other cannabinoids. Therefore, there is a high demand for efficient and broadly applicable chemical glycosylation and glucuronidation of CBD and other cannabinoids, considering the increasing importance of these compounds for potential applications in pharmaceuticals, consumer products, and nutraceuticals. SUMMARY OF THE INVENTION The present disclosure includes novel cannabinoid glycoside compounds, and their methods of synthesis. In one preferred aspect, one or more a glycosyl groups are attached to an aglycone, such as Cannabidiol (CBD), Cannabinol (CBN), Cannabigerol (CBG), Cannabichromene (CBC), Tetrahydrocannabivarin (THCV), Tetrahydrocannabinol (THC), through a ^^- or ^^-glycosidic bond. In one preferred embodiment, one or more a glycosyl groups are attached to an aglycone, such as CBD, CBN, THCV, or THC through a plurality of ^^- glycosidic bonds. Additional aspects of the disclosure include methods of synthesizing a cannabinoid glycoside compound one or more a glycosyl groups are attached to an aglycone, such as CBD or CBN, through a ^^- or ^^-glycosidic bond. The present disclosure includes novel cannabinoid glucuronide compounds, and their methods of synthesis. In one preferred aspect, one or more a glucuronoside donors are attached to an aglycone, such as Cannabidiol (CBD), Cannabinol (CBN), Cannabigerol (CBG), Cannabichromene (CBC), Tetrahydrocannabivarin (THCV), Tetrahydrocannabinol (THC) Another aspect the cannabinoid glycoside and / or glucuronoside compounds of the disclosure are prodrugs. In a preferred aspect of the current disclosure includes pharmaceutical compositions containing one or more cannabinoid glycoside and / or glucuronoside prodrug compounds of the disclosure, and their use to treat one or more disease conditions in a subject in need thereof. Another aspect of the current disclosure includes consumer products, such as food and beverage additives, nutraceuticals, topical compositions, all containing one or more cannabinoid glycoside and / or glucuronoside compounds of the disclosure of the disclosure. Additional aspects of the disclosure may become evident based on the specification and figures presented below. BRIEF DESCRIPTION OF THE DRAWINGS FIG. 1:1H NMR spectrum (300 MHz, CDCl3, 300 K) of O-TMS CBD-1’-O-^^-D- glucoside 2a. FIG.2: Comparison of the1H NMR spectra of CBD-1’-O-^^-D-glucoside (3) derived from both fermentative and synthetic methods. FIG. 3: Comparison of the1H NMR spectra of CBD-1',3'-di-O-^^-D-glucoside (8) derived from both fermentative and synthetic methods. FIG.4:1H NMR spectrum (300 MHz, CD3OD, 300 K) of CBN-1-O-^^-D-glucoside (13). FIG.5:1H NMR spectrum (300 MHz, CD3OD, 300 K) of CBN-1-O-^^-D-glucoside (14). FIG.6: Comparison of the1H NMR spectra of CBN-1-O-^^-D-glucoside (13) derived from both Examples 4 and 6. FIG.7:1H NMR spectrum (300 MHz, CD3OD, 300 K) of CBN-1-O-^^-maltoside (18). FIG.8:1H NMR spectrum (300 MHz, CD3OD, 300 K) of CBN-1-O-^^-maltotrioside (21). DETAILED DESCRIPTION OF THE INVENTION This disclosure provides efficient methods for preparing CBD and CBN glycosides using readily available glycosyl donors. In these methods, a glycosyl group is attached to the aglycones, such as CBD or CBN, through a ^^- or ^^-glycosidic bond. The synthesis of CBD and CBN glucuronides and their salt forms are also provided. The potential use of these glycosides and glucuronides as prodrugs of aglycones or as physiochemically and pharmacologically improved agents is also described. In one embodiment, the present disclosure includes a cannabinoid glycoside according to Formula (III): wherein: R1 is ^^-D-glucopyranosyl- ^^-D-glucopyranosyl-R3, ^^-D-galactopyranosyl-R3, ^^-D- galactopyranosyl-R3, or ^^-L-rhamnopyranosyl-R3; R2is linear alkane; R3is absent, -(1➝6)-^^-D-glucopyranoside, -(1➝4)-^^-D-glucopyranoside, -(1➝4)-^^-D- glucopyranosyl-(1➝4)-^^-D-glucopyranoside, -(1➝4)-^^-D-glucopyranosyl-(1➝4)-^^-D- glucopyranoside, or -(1➝6)-^^-D-glucopyranosyl-(1➝4)-^^-D-glucopyranoside; or a pharmaceutically acceptable salt thereof. In another embodiment, the present disclosure includes a cannabinoid glycoside according to Formula (I): wherein: R1is ^^-D-glucopyranosyl-R4, ^^-D-glucopyranosyl-R4, or ^^-D-galactopyranosyl-R4, ^^-D- galactopyranosyl-R4, or ^^-L-rhamnopyranosyl-R4; R2is H; R3is linear alkane; R4is absent, -(1➝6)-^^-D-glucopyranoside, -(1➝4)-^^-D-glucopyranoside, -(1➝4)-^^-D- glucopyranosyl-(1➝4)-^^-D-glucopyranoside, -(1➝4)-^^-D-glucopyranosyl-(1➝4)-^^-D- glucopyranoside, or -(1➝6)-^^-D-glucopyranosyl-(1➝4)-^^-D-glucopyranoside; or a pharmaceutically acceptable salt thereof. In another embodiment, the present disclosure includes a cannabinoid glycoside according to Formula (III): wherein: R1is a ^^-D-glucoside, ^^ -isomaltoside, ^^ -maltoside, ^^ -lactoside, or ^^ - maltotrioside, ^^-melibioside, ^^-rutinoside; ^^-cellotrioside; or ^^-panoside; R2is a linear alkane; or a pharmaceutically acceptable salt thereof. In another embodiment, the present disclosure includes a cannabinoid glycoside according to Formula (I): , wherein: R1is a ^^-D-glucoside, ^^ -isomaltoside, ^^ -maltoside, ^^ -lactoside, or ^^ - maltotrioside, ^^-melibioside, ^^-rutinoside; ^^-cellotrioside; or ^^-panoside; R2is H; R3is a linear alkane; or a pharmaceutically acceptable salt thereof. In another embodiment, the present disclosure includes a cannabinoid glycoside according any of Formulas I or III, wherein the linear alkane includes a C5linear alkane. In another embodiment, the present disclosure includes a cannabinoid glycoside according to Formula (II): , or a pharmaceutically In another embodiment, a cannabinoid glycoside according to Formula (IV): , or a pharmaceutically In another embodiment, the present disclosure includes a cannabinoid glycoside according to Formula (V): , or a pharmaceutically In another embodiment, the present disclosure includes a cannabinoid glycoside according to Formula (VI): (VI), or a pharmaceutically acce In another embodiment, the present disclosure includes a cannabinoid glycoside accordingula (VII): , or a pharmaceutically In another embodiment, the present disclosure includes a cannabinoid glycoside accordingula (VIII): , or a In another embodiment, the present disclosure includes a cannabinoid glycoside accordingula (IX): X), or a pharmaceutically ac In another embodiment, the present disclosure includes a cannabinoid glycoside according to Formula (X): , or a pharmaceutically In another embodiment, the present disclosure includes a cannabinoid glycoside according to Formula (XI): , or a pharmaceutically In another embodiment, the present disclosure includes a cannabinoid glycoside according to Formula (XII): I), or a pharmaceut In another embodiment, the present disclosure includes a cannabinoid glycoside selected from: CBN-1-O-^^-glucoside; CBN-1-O-^^-isomaltoside; CBN-1-O-^^-maltoside; CBN-1-O-^^-lactoside; CBN-1-O-^^-maltotrioside, CBN-1-O-^^-melibioside; CBN-1-O-^^-rutinoside; CBN-1-O-^^-cellotrioside; CBN-1-O-^^-panoside; or a pharmaceutically acceptably salt of the same. In another embodiment, the present disclosure includes a cannabinoid glycoside selected from: CBN-1-O-^^-D-glucopyranosyl; CBN-1-O-^^-D-glucopyranosyl-(1➝6)-^^-D-glucopyranoside; CBN-1-O-^^-D-glucopyranosyl-(1➝4)-^^-D-glucopyranoside; CBN-1-O-^^-D-galactopyranosyl-(1➝4)-^^- D-glucopyranoside; CBN-1-O-^^-D-glucopyranosyl-(1➝4)-^^-D-glucopyranosyl-(1➝4)-^^-D- glucopyranoside; CBN-1-O-^^-D-galactopyranosyl-(1➝6)-^^-D-glucopyranoside; CBN-1-O-^^-L- rhamnopyranosyl-(1➝6)-^^-D-glucopyranoside; CBN-1-O-^^-D-glucopyranosyl-(1➝4)-^^-D- glucopyranosyl-(1➝4)-^^-D-glucopyranoside; CBN-1-O-^^-D-glucopyranosyl-(1➝6)-^^-D- glucopyranosyl-(1➝4)-^^-D-glucopyranoside; or a pharmaceutically acceptably salt of the same. In another embodiment, the present disclosure includes a cannabinoid glycoside selected from: CBD-1’-O-^^-glucoside; CBD-1’-O-^^-isomaltoside; CBD-1’-O-^^-maltoside; CBD-1’-O- ^^-lactoside; CBD-1’-O-^^-maltotrioside; CBD-1’-O-^^-melibioside; CBD-1’-O-^^-rutinoside; CBD- 1’-O-^^-cellotrioside; CBD-1’-O-^^-panoside; or a pharmaceutically acceptably salt of the same. In another embodiment, the present disclosure includes a cannabinoid glycoside selected from: CBD-1’-O-^^-D-glucopyranosyl; CBD-1’-O-^^-D-glucopyranosyl-(1➝6)-^^-D-glucopyranoside; CBD-1’-O-^^-D-glucopyranosyl-(1➝4)-^^-D-glucopyranoside; CBD-1’-O-^^-D-galactopyranosyl-(1➝4)- ^^-D-glucopyranoside; CBD-1’-O-^^-D-glucopyranosyl-(1➝4)-^^-D-glucopyranosyl-(1➝4)-^^-D- glucopyranoside; CBD-1’-O-^^-D-galactopyranosyl-(1➝6)-^^-D-glucopyranoside; CBD-1’-O-^^-L- rhamnopyranosyl-(1➝6)-^^-D-glucopyranoside; CBD-1’-O-^^-D-glucopyranosyl-(1➝4)-^^-D- glucopyranosyl-(1➝4)-^^-D-glucopyranoside; CBD-1’-O-^^-D-glucopyranosyl-(1➝6)-^^-D- glucopyranosyl-(1➝4)-^^-D-glucopyranoside; or a pharmaceutically acceptably salt of the same. Additional embodiments of the disclosure include a pharmaceutical composition comprising at least one of the compounds of any of Formula I-XXVIII, and a pharmaceutically acceptable carrier. The cannabinoid glycosides compounds of the disclosure, preferably in the form of a pharmaceutical compositions may include a method for treating a disease condition, comprising the steps of administering a therapeutically effective amount of a pharmaceutical composition containing compositions of Formula I-XXVIII to a subject in need thereof. In one embodiment of the disclosure, a therapeutically effective amount of one or more cannabinoid glycosides, may be administered to a subject in need thereof, by a route selected from the group consisting of: transdermal, topical, oral, buccal, sublingual, intra-venous, intra-muscular, vaginal, rectal, ocular, nasal and follicular. Exemplary, disease conditions that can be treated by a cannabinoid prodrug compounds such as a cannabinoid glycoside or glucuronide of the disclosure may be selected from the group consisting of: obesity, post-traumatic stress syndrome, anorexia, nausea, emesis, pain, wasting syndrome, HIV-wasting, chemotherapy induced nausea and vomiting, alcohol use disorders, anti- tumor, amyotrophic lateral sclerosis, glioblastoma multiforme, glioma, increased intraocular pressure, glaucoma, cannabis use disorders, Tourette's syndrome, dystonia, multiple sclerosis, inflammatory bowel disorders, arthritis, dermatitis, Rheumatoid arthritis, systemic lupus erythematosus, anti-inflammatory, anti-convulsant, anti-psychotic, anti-oxidant, neuroprotective, anti-cancer, immunomodulatory effects, peripheral neuropathic pain, neuropathic pain associated with post-herpetic neuralgia, diabetic neuropathy, shingles, burns, actinic keratosis, oral cavity sores and ulcers, post-episiotomy pain, psoriasis, pruritis, contact dermatitis, eczema, bullous dermatitis herpetiformis, exfoliative dermatitis, mycosis fungoides, pemphigus, severe erythema multiforme (e.g., Stevens-Johnson syndrome), seborrheic dermatitis, ankylosing spondylitis, psoriatic arthritis, Reiter's syndrome, gout, chondrocalcinosis, joint pain secondary to dysmenorrhea, fibromyalgia, musculoskeletal pain, neuropathic-postoperative complications, polymyositis, acute nonspecific tenosynovitis, bursitis, epicondylitis, post-traumatic osteoarthritis, synovitis, and juvenile rheumatoid arthritis. One embodiment of the disclosure includes compositions of matter containing one or more cannabinoid glycosides or glucuronides, and preferably consumer products containing one or more of the cannabinoid glycosides or glucuronides according to Formulas I-XXVIII. One embodiment of the disclosure includes compositions of matter containing one or more cannabinoid glycosides or glucuronides, and preferably food and drink additives containing one or more of the cannabinoid glycosides according to Formulas I-XXVIII. One embodiment of the disclosure includes compositions of matter containing one or more cannabinoid glycosides or glucuronides, and preferably topical compositions containing one or more cannabinoid glycosides or glucuronides according to Formulas I-XXVIII. One embodiment of the disclosure includes compositions of matter containing one or more cannabinoid glycosides or glucuronides, and preferably nutraceutical and OTC medication compositions containing one or more cannabinoid glycosides according to Formulas I-XXVIII. One embodiment of the disclosure includes medicaments containing one or more cannabinoid glycosides or glucuronides for the treatment of a disease or condition containing one or more cannabinoid glycosides or glucuronides according to Formulas I-XXVIII. In one embodiment, the disclosure includes a method of synthesizing CBD-1’-O-^^-D- glucoside (3) and CBD-1’,3’-di-O-^^-D-glucoside (8) according to Scheme 2 as described herein. In a preferred embodiment, the method includes: (a) reacting α-glucosyl iodide (6) with CBD under conditions to form O-TMS CBD-1’-O- ^^-D-glucoside (2) and O-TMS CBD-1’,3’-di-O-^^-D-glucoside (7); (b) deprotecting compounds 2 and 7 under conditions that form CBD-1’-O-^^-D-glucoside (3) according to the formula (XIX):

[0002] CBD-1’,3’-di-O-^^-D-glucoside (8) according to the formula (XXI): . In a further of isolating the CBD-1’-O-^^-D- glucoside (3) and / or the CBD- . a further embodiment, the step of reacting includes reacting α-glucosyl iodide (6) with CBD comprises reacting α-glucosyl iodide (6) with CBD in the presence of benzyltriethylammonium chloride (BTEAC), dichloromethane (DCM), water, and NaOH under a nitrogen atmosphere. In one embodiment, the disclosure includes a method of synthesizing a CBD-1’,3’-di-O- ^^-D-glucoside according to Scheme 4 as described herein. In a preferred embodiment, the method includes: (a) reacting α-glucosyl iodide (6) under conditions that causes in situ anomerization forming ^^-glucosyl iodide (5); (b) reacting the glucosyl iodide (5) with CBD under conditions to form CBD-1’,3’-di-O- ^^-D-glucoside (9) according to the formula (II): . In a further embodiment, (6) includes the step of reacting α-glucosyl iodide (6) with NaI or tetrabutylammonium iodide (TBAI) to form ^^-glucosyl iodide (5) via in situ anomerization. In a further embodiment, the step of reacting includes reacting glucosyl iodide (5) with CBD comprises the step of reacting glucosyl iodide (5) with CBD in the presence of benzyltriethylammonium chloride (BTEAC), dichloromethane (DCM), water, NaOH, followed by the step of deprotection using methanol (MeOH) or acetic acid (AcOH) in MeOH. In one embodiment, the disclosure includes a method of synthesizing CBD-1-O-^^-D- glucose according to Scheme 5 as described herein. In a preferred embodiment, the method includes: (a) reacting CBD with acetobromo-^^-D-glucose (10) under conditions that form CBD-1’- O-^^-D-glucoside (3) according to formula (XIX): . In a further reacting CBD with acetobromo- ^^-D-glucose (10) in the presence chloride (BTEAC), dichloromethane (DCM), water, NaOH, followed by the step of deprotection using potassium carbonate (K2CO3) and methanol (MeOH). In a further embodiment, the method includes the step of reacting CBD with acetobromo-^^-D-glucose (10) in the presence of K2CO3, water, tetrabutylammonium bromide (TBABr), MeOH and DCM. In one embodiment, the disclosure includes a method of synthesizing CBN-1-O-^^-D- glucoside (13), and CBN-1-O-^^-D-glucoside (14) according to Scheme 6 as described herein. In a preferred embodiment, the method includes: (a) reacting CBN with ^^-glucosyl iodide (6) under conditions that form CBN-1-O-^^-D- glucoside (13) according to formula (XXIII): (XXIII), and CBN-1-O-^^-D-glucoside (14) according to formula (IV): V). In a further embodimen of reacting includes reacting CBN with ^^-glucosyl iodide (6) in the presence of benzyltriethylammonium chloride (BTEAC), dichloromethane (DCM), water, NaOH followed by the step of deprotection using acetic acid (AcOH) in MeOH and HCl in dioxane. In one embodiment, the disclosure includes a method of synthesizing CBN-1-O-^^- isomaltoside (16) according to Scheme 6 as described herein. In a preferred embodiment, the method includes: (a) reacting CBN with ^^-isomaltosyl iodide (15) under conditions that form CBN-1-O-^^- isomaltoside (16) according to formula (V): . In a further CBN with ^^-isomaltosyl iodide (15) in the presence of benzyltriethylammonium chloride (BTEAC), dichloromethane (DCM), water, NaOH following by the step of deprotection using HCl in dioxane. In one embodiment, the disclosure includes a method of synthesizing CBN-1-O-^^-D- glycoside according to Scheme 7 as described herein. In a preferred embodiment, the method includes: (a) reacting CBN with ^^-D-glucose pentaacetate (17) under conditions that form CBN-1- O-^^-D-glycoside according to formula (XXIII): I). In a further embodime reacting CBN with ^^-D-glucose pentaacetate (17) in the presence of a Lewis acid such as BF3 • OEt2, a base such as triethylamine (NEt3), a solvent such as DCM or CH3CN, followed by the step of deprotection using K2CO3, and MeOH. In one embodiment, a Lewis acid is selected from BF3• OEt2, FeCl3, TMSOTf, AgOTf, or Ag2O. In one embodiment, the disclosure includes a method of synthesizing CBN di- and tri- glycoside according to a modified Scheme 7 as described herein. In a preferred embodiment, the method includes: (a) reacting CBN with a glycosyl donor selected from: , wherein the step of reacting is under conditions that form a CBN di- and tri-glycoside is selected from: . with the ^^- glycosyl donor in the presence of benzyltriethylammonium chloride (BTEAC), dichloromethane (DCM), water, NaOH following by the step of deprotection using HCl in dioxane. In one embodiment, the disclosure includes a method of synthesizing CBN-1-O-^^-D- glucuronide and its salt according to a Scheme 8 as described herein. In a preferred embodiment, the method includes: (a) reacting CBN with a glucuronide donor (26) according to formula:

[0003] wherein said step of reacting is under conditions that form CBN-1-O-^^-D-glucuronide (27) according to formula (XXIV): , In a further step of reacting the CBN-1-O-^^- D-glucuronide (27) with an CBN-1-O-^^-D-glucuronate (28) salt according to Formula (XXV): . In a further CBN with the glucuronide donor (26) in the presence of a Lewis acid such as BF3• OEt2, a base such as triethylamine (NEt3), a solvent such as DCM or CH3CN, followed by the step of deprotection using K2CO3, and MeOH. In one embodiment, a Lewis acid is selected from BF3 • OEt2, FeCl3, TMSOTf, AgOTf, or Ag2O. In a further embodiment the step reacting the CBN-1-O-^^-D-glucuronide (27) with an amino acid includes reacting CBN-1-O-^^-D-glucuronide (27) with arginine in the presence of MeOH and water. In one embodiment, the disclosure includes a method of synthesizing CBD-1’-O-^^-D- glucuronide and its salt according to a Scheme 9 as described herein. In a preferred embodiment, the method includes: (a) reacting per-O-TMS glucuronate (29) with iodotrimethylsilane (TMSI) under conditions to form O-TMS glucuronate iodide (30); (b) reacting CBD with the O-TMS glucuronate iodide (30) under conditions to form an intermediate compound according to formula: 1) (c) deprotecting the imm onditions forming CBD-1’-O-^^-D- glucuronide according to Formula (XXVI): D- (XXVII) wherein M is arginine or Na. In a further embodiment, the step of reacting comprising reacting CBD with the O-TMS glucuronate iodide (30) in the presence of BTEAC, water, DCM and NaOH. In a further embodiment, the step of deprotecting comprises reacting intermediate compound (31) with HCl or K2CO3 and MeOH. In a further embodiment, the step of converting comprises reacting CBD- 1’-O-^^-D-glucuronide with L-arginine and MeOH. In one embodiment, the present disclosure includes a cannabinoid glycoside according to Formula (XIII): II) wherein R1is H, ^^-D-glucopyranosyl-R , -D-glucopyranosyl-R , -D-galactopyranosyl-R3, ^^-D- galactopyranosyl-R3, or ^^-L-rhamnopyranosyl-R3; R2is H; R3is absent, -(1➝6)-^^-D-glucopyranoside, -(1➝4)-^^-D-glucopyranoside, -(1➝4)-^^-D- glucopyranosyl-(1➝4)-^^-D-glucopyranoside, -(1➝4)-^^-D-glucopyranosyl-(1➝4)-^^-D- glucopyranoside, or -(1➝6)-^^-D-glucopyranosyl-(1➝4)-^^-D-glucopyranoside; or a pharmaceutically acceptable salt thereof. In another embodiment, the present disclosure includes a cannabinoid glycoside according to Formula (XIII): wherein R1is H, ^^-D-glucoside, ^^-isomaltoside, ^^-maltoside, ^^-lactoside, or ^^-maltotrioside, ^^- melibioside, ^^-rutinoside; ^^-cellotrioside; ^^-panoside; R2is H; or a pharmaceutically acceptable salt thereof. In another embodiment, the present disclosure includes a cannabinoid glycoside according to Formula (XIV): , or a In another embodiment, the present disclosure includes a method of synthesizing cannabigerol (CBG)-1’-O-^^-D-glucoside (36) according to Scheme 10 as described herein. In another embodiment, the present disclosure includes a method of synthesizing a CBG glycoside, the method including: (a) reacting α-glucosyl iodide (6) with CBG (34) to form O-TMS CBG-1’-O-^^-D-glucoside, and (b) deprotecting O-TMS CBG-1’-O-^^-D-glucoside under conditions that form CBG-1’-O-^^-D-glucoside (36) according to the formula (XIV): (XIV). In one embodiment, reacting α-glucosyl iodide (6) with CBG in the presence of benzyltriethylammonium chloride (BTEAC), dichloromethane (DCM), water, and NaOH under a nitrogen atmosphere. In another embodiment, the present disclosure includes a method of synthesizing CBG-1’- O-^^-D-glucuronide according to a Scheme 12 as described herein. In another embodiment, the present disclosure includes a method of synthesizing a CBG glucuronide, the method including: (a) reacting CBG (34) with the O-TMS glucuronate iodide (30) under conditions to form CBG-1’-O-^^-D-glucuronide (42) according to Formula (XX): . In this the reacted O-TMS glucuronate iodide (30). In this embodiment, the step of deprotecting can include reacting the O- TMS glucuronate iodide (30) that has been reacted with CBG with HCl or K2CO3and MeOH. In this embodiment, the step of reacting can include reacting CBG (34) with the O-TMS glucuronate iodide (30) in the presence of BTEAC, water, DCM and NaOH. In one embodiment, the present disclosure includes a cannabinoid glycoside according to Formula (XV): V), wherein R1is H, ^^-D-glucopyranosyl-R , -D-glucopyranosyl-R , -D-galactopyranosyl-R2, ^^-D- galactopyranosyl-R2, or ^^-L-rhamnopyranosyl-R2; R2is absent, -(1➝6)-^^-D-glucopyranoside, -(1➝4)-^^-D-glucopyranoside, -(1➝4)-^^-D- glucopyranosyl-(1➝4)-^^-D-glucopyranoside, -(1➝4)-^^-D-glucopyranosyl-(1➝4)-^^-D- glucopyranoside, or -(1➝6)-^^-D-glucopyranosyl-(1➝4)-^^-D-glucopyranoside; or a pharmaceutically acceptable salt thereof. In another embodiment, the present disclosure includes a cannabinoid glycoside according to Formula (XV): (XV), wherein R1is ^^-D-glucoside, ^^-isomaltoside, ^^-maltoside, ^^-lactoside, or ^^-maltotrioside, ^^- melibioside, ^^-rutinoside; ^^-cellotrioside; ^^-panoside; or a pharmaceutically acceptable salt thereof. In another embodiment, the present disclosure includes a cannabinoid glycoside according to Formula (XVI): , or a pharmaceutically In another embodiment, the present disclosure includes a method of synthesizing cannabichromene (CBC)-1’-O-^^-D-glucoside (37) according to Scheme 10 as described herein. In another embodiment, the present disclosure includes a method of synthesizing a CBC glycoside, the method including: (a) reacting α- glucosyl iodide (6) with CBC (35) to form O-TMS CBC-1’-O-^^-D-glucoside; and (b) deprotecting O-TMS CBC-1’-O-^^-D-glucoside under conditions that form CBC-1’-O-^^-D-glucoside (37) according to the formula (XVI): . In a preferred α- glucosyl iodide (6) with CBC in the presence of benzyltriethylammonium chloride (BTEAC), dichloromethane (DCM), water, and NaOH under a nitrogen atmosphere. In another embodiment, the present disclosure includes a method of synthesizing CBC-1’- O-^^-D-glucuronide according to a Scheme 12 as described herein. In another embodiment, the present disclosure includes a method of method of synthesizing a CBC glucuronide, the method including: (a) reacting CBC (35) with the O-TMS glucuronate iodide (30) under conditions to form CBC-1’-O-^^-D-glucuronide (43) according to Formula (XVII): (XVII). In a preferred embodiment the step of reacting can include deprotecting the reacted O-TMS glucuronate iodide (30). In a preferred embodiment the step of deprotecting can include reacting the O-TMS glucuronate iodide (30) that has been reacted with CBC with HCl or K2CO3and MeOH. In a preferred embodiment the step of reacting can include reacting CBC (35) with the O- TMS glucuronate iodide (30) in the presence of BTEAC, water, DCM and NaOH. In one embodiment, the present disclosure includes a cannabinoid glycoside according to Formula (XVII): (XVII), wherein R1is H, ^^-D-glucopyranosyl-R3, ^^-D-glucopyranosyl-R3, ^^-D-galactopyranosyl-R3, ^^-D- galactopyranosyl-R3, or ^^-L-rhamnopyranosyl-R3; R2is linear alkane; R3is absent, -(1➝6)-^^-D-glucopyranoside, -(1➝4)-^^-D-glucopyranoside, -(1➝4)-^^-D- glucopyranosyl-(1➝4)-^^-D-glucopyranoside, -(1➝4)-^^-D-glucopyranosyl-(1➝4)-^^-D- glucopyranoside, or -(1➝6)-^^-D-glucopyranosyl-(1➝4)-^^-D-glucopyranoside; or a pharmaceutically acceptable salt thereof. In another embodiment, the present disclosure includes a cannabinoid glycoside according to Formula (XVII): (XVII), wherein R1is ^^-D-glucoside, ^^-isomaltoside, ^^-maltoside, ^^-lactoside, or ^^-maltotrioside, ^^- melibioside, ^^-rutinoside; ^^-cellotrioside; ^^-panoside; R1is linear alkane; or a pharmaceutically acceptable salt thereof. In a preferred embodiment, the linear alkane is n-propyl, or n-pentyl. In another embodiment, the present disclosure includes a cannabinoid glycoside according to Formula (XVIII): (XVIII) wherein R1is linear alkane selected from n-propyl, or n-pentyl; or a pharmaceutically acceptable salt thereof. In another embodiment, the present disclosure includes a method of synthesizing cannabichromene tetrahydrocannabivarin (THCV)-1-O-^^-D-glucoside (40) according to Scheme 11 as described herein. In another embodiment, the present disclosure includes a method of synthesizing tetrahydrocannabinol (THC)-1-O-^^-D-glucoside (41) according to Scheme 11 as described herein. In another embodiment, the present disclosure includes a method of synthesizing a cannabinoid glycoside, the method comprising: (a) reacting α-glucosyl iodide (6) or β-D-glucose pentaacetate (17) with THCV (38) or THC (39) under conditions that form: THCV-1-O-^^-D-glucoside (40) according to the formula (XVIII): (XVIII), wherein R1 is n-propyl; or THC-1-O-^^-D-glucoside (41) according to the formula (XVIII): (XVIII), wherein R1 i In a preferred embodiment the step of reacting can include reacting α- glucosyl iodide (6) with THCV (38) or THC (39) in the presence of benzyltriethylammonium chloride (BTEAC), dichloromethane (DCM), water, and NaOH under a nitrogen atmosphere. In another preferred embodiment the step of reacting can include reacting THCV (38) or THC (39) with ^^-D-glucose pentaacetate (17) in the presence of a Lewis acid such as BF3 • OEt2, a base such as triethylamine (NEt3), a solvent such as DCM or CH3CN, followed by the step of deprotection using K2CO3, and MeOH. In one embodiment, the Lewis acid is selected from BF3• OEt2, FeCl3, TMSOTf, AgOTf, or Ag2O. In another embodiment, the present disclosure includes a method of synthesizing THCV- 1-O-^^-D-glucuronide and / or THC-1-O-^^-D- glucuronide according to a Scheme 13 as described herein. In another embodiment, the present disclosure includes a method of synthesizing a cannabinoid glucuronide, the method comprising: (a) reacting THCV (38) or THC (39) with a glucuronide donor selected from: O-TMS glucuronate iodide (30) or methyl glucuronate tetraacetate (26) under conditions that form: THCV-1-O-^^-D-glucuronide (44) according to the formula (XXVIII):

[0004] wherein R1 is n-propyl; or THC-1-O-^^-D-glucuronide (45) according to the formula (XXVIII): (XXVIII), wherein R1 In a preferred embodiment the step of reacting can include reacting THCV (38) or THC (39) with the methyl glucuronate tetraacetate (26) in the presence of a Lewis acid, a base such as triethylamine (NEt3), a solvent such as DCM or CH3CN, followed by the step of deprotection using LIOH, and MeOH. In one embodiment, the Lewis acid is selected from BF3 • OEt2, FeCl3, TMSOTf, AgOTf, or Ag2O. In another preferred embodiment the step of reacting can include reacting THCV (38) or THC (39) with the O-TMS glucuronate iodide (30) in the presence of BTEAC, water, DCM and NaOH. In another preferred embodiment the step of reacting can include the step of deprotecting with HCl or K2CO3and MeOH. In one embodiment, the disclosure includes an isolated cannabinoid glycoside and / or glucuronoside or intermediate compounds synthesized by any of the methods described herein, and a pharmaceutically acceptable carrier. In another embodiment, the disclosure includes pharmaceutical composition comprising a cannabinoid glycoside and / or glucuronoside or intermediate compound synthesized by any of the methods described herein, and a pharmaceutically acceptable carrier. Unless defined otherwise, all technical and scientific terms used herein have the same meaning as commonly understood by one of ordinary skill in the art to which this disclosure belongs. Although any methods and materials similar or equivalent to those described herein can be used in the practice or testing of the present disclosure, the preferred methods and materials are now described. All structures depicted herein, unless otherwise stated include all isomeric (e.g., enantiomeric, diastereomeric, and geometric (or conformational)) forms of the structure; for example, the R and S configurations for each asymmetric center, Z and E double bond isomers, and Z and E conformational isomers. Therefore, single stereochemical isomers as well as enantiomeric, diastereomeric, and geometric (or conformational) mixtures of the present compounds are within the scope of the disclosure. Unless otherwise stated, all tautomeric forms of the compounds of the disclosure are within the scope of the disclosure. Additionally, unless otherwise stated, structures depicted herein are also meant to include compounds that differ only in the presence of one or more isotopically enriched atoms. For example, compounds having the present structures including the replacement of hydrogen by deuterium or tritium, or the replacement of a carbon by a 13C- or 14C-enriched carbon are within the scope of this disclosure. Such compounds are useful, for example, as analytical tools, as probes in biological assays, or as therapeutic agents in accordance with the present disclosure. The term “stereoisomer” refers to a molecule that is an enantiomer, diastereomer or geometric isomer of a molecule. Stereoisomers, unlike structural isomers, do not differ with respect to the number and types of atoms in the molecule's structure but with respect to the spatial arrangement of the molecule's atoms. Examples of stereoisomers include the (+) and (-) forms of optically active molecules. As used herein, the term “cannabinoid” may also include different modified forms of a cannabinoid such as a methylated, acetylated, hydroxylated cannabinoids or cannabinoid carboxylic acids. Examples of cannabinoids are tetrahydrocannabinol, cannabidiol, cannabigerol, cannabichromene, cannabicyclol, cannabivarin, cannabielsoin, cannabicitran, cannabigerolic acid, cannabigerolic acid monomethylether, cannabigerol monomethylether, cannabigerovarinic acid, cannabigerovarin, cannabichromenic acid, cannabichromevarinic acid, cannabichromevarin, cannabidolic acid, cannabidiol monomethylether, cannabidiol-C4, cannabidivarinic acid, cannabidiorcol, delta-9-tetrahydrocannabinolic acid A, delta-9- tetrahydrocannabinolic acid B, delta-9-tetrahydrocannabinolic acid-C4, delta-9- tetrahydrocannabivarinic acid, delta-9- tetrahydrocannabivarin, delta-9- tetrahydrocannabiorcolic acid, delta-9-tetrahydrocannabiorcol, delta-7-cis-iso-tetrahydrocannabivarin, delta-8-tetrahydrocannabiniolic acid, delta-8- tetrahydrocannabinol, cannabicyclolic acid, cannabicylovarin, cannabielsoic acid A, cannabielsoic acid B, cannabinolic acid, cannabinol methyl ether, cannabinol-C4, cannabinol-C2, cannabiorcol, 10-ethoxy-9-hydroxy-delta-6a-tetrahydrocannabinol, 8,9-dihydroxy-delta-6a- tetrahydrocannabinol, cannabitriolvarin, ethoxy-cannabitriolvarin, dehydrocannabifuran, cannabifuran, cannabichromanon, cannabicitran, 10-oxo-delta-6a-tetrahydrocannabinol, delta-9- cis- tetrahydrocannabinol, 3, 4, 5, 6-tetrahydro-7-hydroxy-alpha-alpha-2-trimethyl-9-n- propyl-2, 6-methano-2H-1-benzoxocin-5-methanol-cannabiripsol, trihydroxy-delta-9- tetrahydrocannabinol, and cannabinol. As used herein, an ^^-glycosidic bond is formed when two carbons have the same stereochemistry, whereas a β-glycosidic bond occurs when the two carbons have different stereochemistry. The term “glucopyranoside” is used for naming molecules and is shorthand for a β-D- glucose attached through the hydroxyl at the 1-position (the anomeric carbon) of the glucose to the aglycone. The term “aglycone” is used in the present application to refer to the non-glycosidic portion of a glycoside compound. A “glycoside” is a molecule that contains a sugar molecule attached to another functional group. A “glucuronide,” also known as glucuronoside, is any compound produced by linking glucuronic acid to another substance via a glycosidic bond. The glucuronides belong to the glycosides. As such, in come cases reference to a glycosides can further encompass a glucuronoside. A cannabinoid may include one or more conjugate sites or conjugation sites that can bind to a glycosyl group. As used herein “conjugate site” or “conjugation site” mean a position on a cannabinoid compound that may covalently bind to a glycosyl group, for example through an ^^- or β-glycosidic bond. Exemplary conjugation sites can be shown below in Table B: The term “compound,” or “compound of the disclosure” includes all solvates, complexes, polymorphs, radiolabeled derivatives, tautomers, stereoisomers, and optical isomers of the cannabinoid glycosides and / or glucuronoside compounds generally described herein, and salts thereof, unless otherwise specified. Notably, if the compound is anionic, or has a functional group which may be anionic (e.g., —COOH may be —COO−), then a salt may be formed with a suitable cation. Examples of suitable inorganic cations include, but are not limited to, alkali metal ions such as Na+and K+, alkaline earth cations such as Ca2+and Mg2+, and other cations such as Al3+. Examples of suitable organic cations include, but are not limited to, ammonium ion (i.e., NH4+) and substituted ammonium ions (e.g., NH3R+, NH2R2+, NHR3+, NR4+). Examples of some suitable substituted ammonium ions are those derived from: ethylamine, diethylamine, dicyclohexylamine, triethylamine, butylamine, ethylenediamine, ethanolamine, diethanolamine, piperazine, benzylamine, phenylbenzylamine, choline, meglumine, and tromethamine, as well as amino acids, such as histidine, lysine and arginine. An example of a common quaternary ammonium ion is N(CH3)4+. It may be convenient or desirable to prepare, purify, and / or handle a corresponding solvate of the active compound. The term “solvate” is used herein in the conventional sense to refer to a complex of solute (e.g., active compound, salt of active compound) and solvent. If the solvent is water, the solvate may be conveniently referred to as a hydrate, for example, a mono-hydrate, a di-hydrate, a tri-hydrate, etc. It may be convenient or desirable to prepare, purify, and / or handle the active compound in a chemically protected form. The term “chemically protected form,” as used herein, pertains to a compound in which one or more reactive functional groups are protected from undesirable chemical reactions, that is, are in the form of a protected or protecting group (also known as a masked or masking group or a blocked or blocking group). By protecting a reactive functional group, reactions involving other unprotected reactive functional groups can be performed, without affecting the protected group; the protecting group may be removed, usually in a subsequent step, without substantially affecting the remainder of the molecule. See, for example, “Protective Groups in Organic Synthesis” (T. Green and P. Wuts; 3rd Edition; John Wiley and Sons, 1999). For example, a hydroxy group may be protected as an ether (—OR) or an ester (—OC(═O)R), for example, as: a t-butyl ether; a benzyl, benzhydryl (diphenylmethyl), or trityl (triphenylmethyl)ether; a trimethylsilyl or t-butyldimethylsilyl ether; or an acetyl ester (— OC(═O)CH3, —OAc). For example, an aldehyde or ketone group may be protected as an acetal or ketal, respectively, in which the carbonyl group (>C═O) is converted to a diether (>C(OR)2), by reaction with, for example, a primary alcohol. The aldehyde or ketone group is readily regenerated by hydrolysis using a large excess of water in the presence of acid. For example, an amine group may be protected, for example, as an amide or a urethane, for example, as: a methyl amide (—NHCO—CH3); a benzyloxy amide (—NHCO—OCH2C6H5, —NH-Cbz); as a t-butoxy amide (—NHCO—OC(CH3)3, —NH-Boc); a 2-biphenyl-2-propoxy amide (—NHCO—OC(CH3)2C6H4C6H5, —NH-Bpoc), as a 9-fluorenylmethoxy amide (—NH- Fmoc), as a 6-nitroveratryloxy amide (—NH-Nvoc), as a 2-trimethylsilylethyloxy amide (—NH- Teoc), as a 2,2,2-trichloroethyloxy amide (—NH-Troc), as an allyloxy amide (—NH-Alloc), as a 2(-phenylsulphonyl)ethyloxy amide (—NH-Psec); or, in suitable cases, as an N-oxide (>NO). For example, a carboxylic acid group may be protected as an ester for example, as: a C1-7alkyl ester (e.g., a methyl ester; a t-butyl ester); a C1-7 haloalkyl ester (e.g., a C1-7 trihaloalkyl ester); a triC1- 7 alkylsilyl-C1-7 alkyl ester; or a C5-20 aryl-C1-7 alkyl ester (e.g., a benzyl ester; a nitrobenzyl ester); or as an amide, for example, as a methyl amide. An “R-group” or “substituent” refers to a single atom (for example, a halogen atom) or a group of two or more atoms that are covalently bonded to each other, which are covalently bonded to an atom or atoms in a molecule to satisfy the valency requirements of the atom or atoms of the molecule, typically in place of a hydrogen atom. The term “linear alkane” is used to refer to an alkane in which each carbon atom is bound to a maximum of two carbon atoms. In certain embodiments, it may be convenient or desirable to prepare, purify, and / or handle the active compound in the form of a prodrug. The term “prodrug,” as used herein, pertains to a compound which, when metabolized (e.g., in vivo), yields the desired active compound, for example through the removal of a glycosyl group reconstituting the native cannabinoid compound. Typically, the prodrug is inactive, or less active than the active compound, but may provide advantageous handling, administration, or metabolic properties. “Pharmaceutical compositions” are compositions that include an amount (for example, a unit dosage) of one or more of the disclosed compounds together with one or more non-toxic pharmaceutically acceptable additives, including carriers, diluents, and / or adjuvants, and optionally other biologically active ingredients. Such pharmaceutical compositions can be prepared by standard pharmaceutical Formulation techniques such as those disclosed in Remington's Pharmaceutical Sciences, Mack Publishing Co, Easton, Pa. (19th Edition). The terms “pharmaceutically acceptable salt” refers to salts or esters prepared by conventional means that include salts, e.g, of inorganic and organic acids, including but not limited to hydrochloric acid, hydrobromic acid, sulfuric acid, phosphoric acid, methanesulfonic acid, ethanesulfonic acid, malic acid, acetic acid, oxalic acid, tartaric acid, citric acid, lactic acid, fumaric acid, succinic acid, maleic acid, salicylic acid, benzoic acid, phenylacetic acid, mandelic acid, and the like. For therapeutic use, salts of the compounds are those wherein the counter-ion is pharmaceutically acceptable. However, salts of acids and bases which are non-pharmaceutically acceptable may also find use, for example, in the preparation or purification of a pharmaceutically acceptable compound. The pharmaceutically acceptable acid and base addition salts as mentioned above are meant to comprise the therapeutically active non-toxic acid and base addition salt forms which the compounds can form. The pharmaceutically acceptable acid addition salts can conveniently be obtained by treating the base form with such appropriate acid. Appropriate acids comprise, for example, inorganic acids such as hydrohalic acids, e.g. hydrochloric or hydrobromic acid, sulfuric, nitric, phosphoric and the like acids; or organic acids such as, for example, acetic, propanoic, hydroxyacetic, lactic, pyruvic, oxalic (i.e. ethanedioic), malonic, succinic (i.e. butanedioic acid), maleic, fumaric, malic (i.e. hydroxybutanedioic acid), tartaric, citric, methanesulfonic, ethanesulfonic, benzenesulfonic, p-toluenesulfonic, cyclamic, salicylic, p-aminosalicylic, pamoic, and like acids. Conversely, these salt forms can be converted into the free base form by treatment with an appropriate base. The compounds containing an acidic proton may also be converted into their non-toxic metal or amine addition salt forms by treatment with appropriate organic and inorganic bases. Appropriate base salt forms comprise, for example, the ammonium salts, the alkali and earth alkaline metal salts, e.g. the lithium, sodium, potassium, magnesium, calcium salts and the like, salts with organic bases, e.g. the benzathine, N-methyl-D-glucamine, hydrabamine salts, and salts with amino acids such as, for example, arginine, lysine, and the like. Some of the compounds described herein may also exist in their tautomeric form. The terms “approximately” and “about” refer to a quantity, level, value, or amount that varies by as much as 30%, or in another embodiment by as much as 20%, and in a third embodiment by as much as 10% to a reference quantity, level, value, or amount. As used herein, the singular form “a,” “an,” and “the” include plural references unless the context clearly dictates otherwise. The inventive technology may further include cannabinoid glycosides and / or glucuronosides exhibit increase solubility. In one preferred embodiment, the disclosure may include a pharmaceutical composition as an active ingredient an effective amount or dose of one or more of the cannabinoid glycosides and / or glucuronosides of the disclosure. In some instances, the active ingredient may be provided together with pharmaceutically tolerable adjuvants and / or excipients in the pharmaceutical composition. Such pharmaceutical composition may optionally be in combination with one or more further activeingredients. In one embodiment, one of the aforementioned the cannabinoid glycosides and / or glucuronosides of the disclosure is a prodrug, whereby a sugar promoiety may be removed after administration and / or uptake of a therapeutically effective amount, or effective dose, or dose. The terms “therapeutically effective amount” or “effective dose” or “dose” are interchangeably used herein and denote an amount of the pharmaceutical compound having a prophylactically or therapeutically relevant effect on a disease or pathological conditions, i.e. which causes in a tissue, system, animal or human a biological or medical response which is sought or desired, for example, by a researcher or physician. Pharmaceutical Formulations can be administered in the form of dosage units which comprise a predetermined amount of active ingredient per dosage unit. The concentration of the prophylactically or therapeutically active ingredient in the Formulation may vary from about 0.1 to 100 wt %. Preferably, a cannabinoid glycoside and / or glucuronoside of the disclosure or the pharmaceutically acceptable salts thereof are administered in doses of approximately 0.5 to 1000 mg, more preferably between .1mg and 1000mg, 1 and 700 mg, and most preferably 5 and 100 mg per dose unit. Generally, such a dose range is appropriate for total daily incorporation. In other terms, the daily dose is preferably between approximately 0.02 and 100 mg / kg of body weight. The specific dose for each patient depends, however, on a wide variety of factors as already described in the present specification (e.g. depending on the condition treated, the method of administration and the age, weight, and condition of the patient). Preferred dosage unit Formulations are those which comprise a daily dose or part-dose, as indicated above, or a corresponding fraction thereof of an active ingredient. Furthermore, pharmaceutical Formulations of this type can be prepared using a process which is generally known in the pharmaceutical art. As used herein, a consumer product, including a food additive, a beverage additive as well as nutraceutical compositions are described by Sayre et al., in U.S. Application No.16 / 110,954. The descriptions of the compositions in paragraphs 0206 to 0251, and the section entitled Preserved Clauses at paragraphs 0358 to 0427, being specifically incorporated hereby reference incorporate by reference. In one embodiment, the disclosure may include one or more methods of treating a medical condition in a mammal. In this embodiment, the novel method may include of administering a therapeutically effective amount of one or more of the cannabinoid glycosides and / or glucuronosides of the disclosure, wherein the medical condition is selected from the group consisting of: obesity, post-traumatic stress syndrome, anorexia, nausea, emesis, pain, wasting syndrome, HIV-wasting, chemotherapy induced nausea and vomiting, alcohol use disorders, anti- tumor, amyotrophic lateral sclerosis, glioblastoma multiforme, glioma, increased intraocular pressure, glaucoma, cannabis use disorders, Tourette's syndrome, dystonia, multiple sclerosis, inflammatory bowel disorders, arthritis, dermatitis, Rheumatoid arthritis, systemic lupus erythematosus, anti-inflammatory, anti-convulsant, anti-psychotic, anti-oxidant, neuroprotective, anti-cancer, immunomodulatory effects, peripheral neuropathic pain, neuropathic pain associated with post-herpetic neuralgia, diabetic neuropathy, shingles, burns, actinic keratosis, oral cavity sores and ulcers, post-episiotomy pain, psoriasis, pruritis, contact dermatitis, eczema, bullous dermatitis herpetiformis, exfoliative dermatitis, mycosis fungoides, pemphigus, severe erythema multiforme (e.g, Stevens-Johnson syndrome), seborrheic dermatitis, ankylosing spondylitis, psoriatic arthritis, Reiter's syndrome, gout, chondrocalcinosis, joint pain secondary to dysmenorrhea, fibromyalgia, musculoskeletal pain, neuropathic-postoperative complications, polymyositis, acute nonspecific tenosynovitis, bursitis, epicondylitis, post-traumatic osteoarthritis, synovitis, and juvenile rheumatoid arthritis. In a preferred embodiment, the pharmaceutical composition may be administered by a route selected from the group consisting of transdermal, topical, oral, buccal, sublingual, intra-venous, intra-muscular, vaginal, rectal, ocular, nasal, and follicular. The amount of cannabinoid glycosides and / or glucuronosides may be a therapeutically effective amount, which may be determined by the patient’s age, weight, medical condition cannabinoid-delivered, route of delivery, and the like. In one embodiment, a therapeutically effective amount may be 50 mg or less of a cannabinoid glycoside and / or glucuronoside. In another embodiment, a therapeutically effective amount may be 50 mg or more of a cannabinoid glycoside and / or glucuronoside. It should be noted that for any of the above composition, unless otherwise stated, an effective amount of a cannabinoid glycoside may include amounts between: .01mg to .1 mg; .01mg to .5 mg; .01mg to 1 mg; .01mg to 5 mg; .01mg to 10 mg; .01mg to 25 mg; .01mg to 50 mg; .01mg to 75 mg; .01mg to 100 mg; .01mg to 125 mg; .01mg to 150 mg; .01mg to 175 mg; .01mg to 200 mg; .01mg to 225 mg; .01mg to 250 mg; .01mg to 275 mg; .01mg to 300 mg; .01mg to 225 mg; .01mg to 350 mg; .01mg to 375 mg; .01mg to 400 mg; .01mg to 425 mg; .01mg to 450 mg; .01mg to 475 mg; .01mg to 500 mg; .01mg to 525 mg; .01mg to 550 mg; .01mg to 575 mg; .01mg to 600 mg; .01mg to 625 mg; .01mg to 650 mg; .01mg to 675 mg; .01mg to 700 mg; .01mg to 725 mg; .01mg to 750 mg; .01mg to 775 mg; .01mg to 800 mg; .01mg to 825 mg; .01mg to 950 mg; .01mg to 875 mg; .01mg to 900 mg; .01mg to 925 mg; .01mg to 950 mg; .01mg to 975 mg; .01mg to 1000 mg; .01mg to 2000 mg; .01mg to 3000 mg; .01mg to 4000 mg; 01mg to 5000 mg; .01mg to .1 mg / kg.; .01mg to .5 mg / kg; 01mg to 1 mg / kg; .01mg to 5 mg / kg; .01mg to 10 mg / kg; .01mg to 25 mg / kg; .01mg to 50 mg / kg; .01mg to 75 mg / kg; and .01mg to 100 mg / kg. The cannabinoid glycoside and / or glucuronoside compounds of the present disclosure are useful for a variety of therapeutic applications. For example, the compounds are useful for treating or alleviating symptoms of diseases and disorders involving CB1, CB2, GPR119, 5HT1A, μ and δ- OPR receptors, and TRP channels, including appetite loss, nausea and vomiting, pain, multiple sclerosis, and epilepsy. For example, they may be used to treat pain (i.e. as analgesics) in a variety of applications including but not limited to pain management. In additional embodiments, such cannabinoid glycosides and / or glucuronosides may be used as an appetite suppressant. Additional embodiments may include administering the cannabinoid glycoside and / or glucuronoside compounds to a subject in need thereof. By “treating,” the present inventors mean that the compound is administered in order to alleviate symptoms of the disease or disorder being treated. Those of skill in the art will recognize that the symptoms of the disease or disorder that is treated may be completely eliminated or may simply be lessened. Further, the compounds may be administered in combination with other drugs or treatment modalities, such as with chemotherapy or other cancer-fighting drugs. Implementation may generally involve identifying patients suffering from the indicated disorders and administering the compounds of the present disclosure in an acceptable form by an appropriate route. The exact dosage to be administered may vary depending on the age, gender, weight, and overall health status of the individual patient, as well as the precise etiology of the disease. However, in general, for administration in mammals (e.g. humans), dosages in the range of from about 0.01 to about 300 mg of compound per kg of body weight per 24 hr, and more preferably about 0.01 to about 100 mg of compound per kg of body weight per 24 hr, may be effective. Administration may be oral or parenteral, including intravenously, intramuscularly, subcutaneously, intradermal injection, intraperitoneal injection, etc, or by other routes (e.g. transdermal, sublingual, oral, rectal, and buccal delivery, inhalation of an aerosol, etc.). In a preferred embodiment of the disclosure, the cannabinoid glycosides and / or glucuronosides are provided orally or intravenously. The compounds may be administered in the pure form or in a pharmaceutically acceptable Formulation including suitable elixirs, binders, and the like (generally referred to as a “secondary carrier”) or as pharmaceutically acceptable salts (e.g. alkali metal salts such as sodium, potassium, calcium or lithium salts, ammonium, etc.) or other complexes. It should be understood that the pharmaceutically acceptable Formulations include liquid and solid materials conventionally utilized to prepare both injectable dosage forms and solid dosage forms such as tablets and capsules and aerosolized dosage forms. In addition, the compounds may be Formulated with aqueous or oil-based vehicles. Water may be used as the carrier for the preparation of compositions (e.g. injectable compositions), which may also include conventional buffers and agents to render the composition isotonic. Other potential additives and other materials (preferably those which are generally regarded as safe [GRAS]) include: colorants; flavorings; surfactants (TWEEN, oleic acid, etc.); solvents, stabilizers, elixirs, and binders or encapsulants (lactose, liposomes, etc). Solid diluents and excipients include lactose, starch, conventional disintergrating agents, coatings, and the like. Preservatives such as methyl paraben or benzalkium chloride may also be used. Depending on the formulation it is expected that the active composition will consist of about 1% to about 99% of the composition and the secondary carrier will constitute about 1% to about 99% of the composition. The pharmaceutical compositions of the present disclosure may include any suitable pharmaceutically acceptable additives or adjuncts to the extent that they do not hinder or interfere with the therapeutic effect of the active compound. The administration of the compounds of the present disclosure may be intermittent, bolus dose, or at a gradual or continuous, constant, or controlled rate to a patient. In addition, the time of day and the number of times per day that the pharmaceutical Formulation is administered may vary and are best determined by a skilled practitioner such as a physician. Further, the effective dose can vary depending upon factors such as the mode of delivery, gender, age, and other conditions of the patient, as well as the extent or progression of the disease. The compounds may be provided alone, in a mixture containing two or more of the compounds, or in combination with other medications or treatment modalities. As used herein the singular forms “a,” “an,” and “the” include plural referents unless the context clearly dictates otherwise. Thus, for example, reference to “a compound” includes a plurality of such compounds, and reference to “the method” includes reference to one or more methods, method steps, and equivalents thereof known to those skilled in the art, and so forth. Similarly, the word “or” is intended to include “and” unless the context clearly indicates otherwise. Hence “comprising A or B” means including A, or B, or A and B. Furthermore, the use of the term “including,” as well as other related forms, such as “includes” and “included,” is not limiting. The term “about” as used herein is a flexible word with a meaning similar to “approximately” or “nearly.” The term “about” indicates that exactitude is not claimed, but rather a contemplated variation. Thus, as used herein, the term “about” means within 1 or 2 standard deviations from the specifically recited value, or ± a range of up to 20%, up to 15%, up to 10%, up to 5%, or up to 4%, 3%, 2%, or 1 % compared to the specifically recited value. EXAMPLES Chemical Synthesis of CBD-1’-O-^^-D-glucoside. In one embodiment of the current disclosure, the present inventors demonstrated the chemical synthesis of CBD-1’-O-^^-D-glucoside (3) using ^^-glucosyl iodide 6. Specifically, a method for preparing CBD-1’-O-^^-D-glucoside (3) is provided herein, which employs a reactive per-O-TMS (trimethyl silyl) ^^-glucosyl iodide 6, known as a super armed glucosyl donor, under phase transfer catalyst (PTC) conditions in basic biphasic systems. Scheme 1 illustrates a detailed reaction sequence. Initially, ^^-glucosyl iodide 6 is generated from readily available per-O-TMS glucose 4 by reaction with iodotrimethylsilane (TMSI) following a known procedure (Gervay- Hague et al., Acc Chem Res 2016, 49, 35). The complete conversion of ^^-iodide 5 to ^^-iodide 6 is confirmed by1H NMR analysis of an aliquot of the mixture. The in situ generated ^^-glucosyl iodide 6 in dichloromethane (DCM) is then directly cannulated into a mixture of CBD, benzyltriethylammonium chloride (BETAC), water, and DCM, followed by the addition of NaOH. Upon completion, the crude glycoside is purified by silica gel column chromatography to yield O- TMS CBD-1’-O-^^-D-glucoside 2. During the purification, the TMS group in the primary hydroxyl at the C-6 position of glucose can be deprotected, leading to 2b. The final global deprotection of TMS groups using acetic acid in methanol provides CBD-1’-O-^^-D-glucoside (3). Other deprotection conditions such as HCl solution in dioxane (or isopropyl acetate), K2CO3in methanol, or methanol only can also be successfully used to afford CBD-1’-O-^^-D-glucoside (3) (Examples 1–2).

[0005] Scheme 1. Preparation of CBD-1’-O-^^-D-glucoside (3) in small scale using in situ generated ^^-glucosyl iodide 6 However, this method is not reproducible for a multi-gram scale reaction due to the long addition time of reactive ^^-glucosyl iodide 6. During the addition, it appears that ^^-glucosyl iodide 6 partly deteriorates, resulting in incomplete conversion. A more robust and reproducible method is provided in Scheme 2, where instead of adding reactive ^^-glucosyl iodide 6, a mixture of CBD, BETAC, water, and DCM is added into a solution of ^^-glucosyl iodide 6 in DCM under a nitrogen atmosphere. The reverse addition procedure proceeds smoothly to afford O-TMS CBD-1’-O-^^-D- glucoside 2 in good yield. In this process, a small amount of O-TMS CBD-1’,3’-di-O-^^-D- glucoside (7) is also produced. After deprotection of TMS groups in methanol, CBD-1’-O-^^-D- glucoside (3) is successfully prepared on a multi-gram scale, in addition to CBD-1’,3’-di-O-^^-D- glucoside (8) (Example 3). Scheme 2. Preparation of CBD-1’-O-^^-D-glucoside (3) and CBD-1’,3’-di-O-^^-D-glucoside (8) in multi-gram scale using in situ generated ^^-glycosyl iodide 6 The glycosylation proceeds in a ^^-selective fashion, and the ^^-glycosidic linkage is confirmed by the coupling constant (3J = 7.2 Hz) of the anomeric proton in per-O-TMS CBD-1’- O-^^-D-glucoside 2a (FIG 1). The glycosylation of CBD by fermenting Pichia pastoris harboring a plasmid encoding tobacco-derived glycosyltransferase (NtGT4) also provides CBD-1’-O-^^-D- glucoside (3) and CBD-1’,3’-di-O-^^-D-glucoside (8) (Sayre et al., WO 2019014395 A1 and Huynh et al., WO 2023240221 A2, Trait Biosciences) (Scheme 3). The1H NMR spectra of fermentative-derived CBD glucosides are identical to that of synthetic glycosides 3 and 8, supporting the conclusion that both chemical and fermentative glycosylation of CBD result in a ^^- glycosidic bond. (FIGS 2-3). (NtGT4) Synthesis of CBD-1’-O-^^-D-glucoside (9) using in situ anomerization strategy. In one embodiment of the current disclosure, the present inventors demonstrated the chemical synthesis of CBD-1’-O-^^-D-glucoside utilizing in situ anomerization. The chemical glycosylation method can be adjusted to synthesize CBD-1’-O-^^-D-glucoside (9) by applying an in situ anomerization strategy (Lam et al., Org Lett 2003, 5 (22), 4129; Schombs et al., J Org Chem 2010, 75 (15), 4891). As depicted in Scheme 4, ^^-glucosyl iodide 6 undergoes in situ anomerization by the addition of NaI or tetrabutylammonium iodide (TBAI), leading to reactive ^^-glucosyl iodide 5. This compound then undergoes a nucleophilic attack by CBD under biphasic conditions to produce CBD-1’-O-^^-D-glucoside (9) after the deprotection of TMS groups. Scheme 4. Preparation of CBD-1’-O-^^-D-glucoside (9) via in situ anomerization Synthesis of CBD-1’-O-^^-D-glucoside. In one embodiment of the current disclosure, the present inventors demonstrated the chemical synthesis of CBD-1’-O-^^-D-glucoside (3) using acetobromo-^^-D-glucose (10). Scheme 5 illustrates the glucosylation of CBD with commercially available acetobromo-^^-D-glucose (10). Using a less reactive glucosyl donor 10 instead of ^^-glucosyl iodide 6 under identical conditions results in CBD-1’-O-^^-D-glucoside (3) in two steps, albeit with a low yield (Pathway A). The acetate protected glycoside 11 undergoes a one-pot glucosylation by the addition of methanol to yield CBD-1’-O-^^-D-glucoside (3), as the acetate groups are removed under the conditions (Pathway B). Scheme 5. Preparation of CBD-1’-O-^^-D-glucoside (3) using acetobromo-^^-D-glucose (10) as a glycosyl donor Synthesis of CBN-glycoside variants. In one embodiment of the current disclosure, the present inventors demonstrated the chemical synthesis of CBN-1-O-^^-D-glucoside (13), CBN-1-O-^^-D-glucoside (14) and CBN-1- O-^^-isomaltoside (16). When the chemical glycosylation strategy is applied using either ^^- glucosyl iodide 6 or ^^-isomaltosyl iodide 15 to CBN (12), both CBN-1-O-^^-D-glucoside (13) and CBN-1-O-^^-isomaltoside (16) are respectively obtained (Scheme 6, Examples 4–5, FIG 4). During the glycosylation process of CBN with ^^-glucosyl iodide 6, CBN-1-O-^^-D-glucoside (14), which has an ^^-glycosidic bond, is also formed as a minor product (FIG. 5). This result highlights the utility of the glycosylation protocol in the synthesis of diverse cannabinoid glycosides. Scheme 6. Preparation of CBN-1-O-^^-D-glucoside (13) and its ^^–anomer 14 and CBN-1-O-^^-isomaltoside (16) Synthesis of CBN-1-O-^^-D-glycoside. In one of the current disclosure, the present inventors demonstrated the chemical synthesis 1-O-^^-D-glycoside (13) using ^^-D-glucose pentaacetate (17). Scheme 7 presents an alternative stereoselective synthesis of CBN-1-O-^^-D-glucoside (13) using readily available ^^-D-glucose pentaacetate (17) as a glucosyl donor (Example 6, FIG. 6). In this process, the formation of the glucoside is mediated by BF3 • OEt2. The selective formation of the ^^- glucosidic linkage is governed by a mechanism known as neighboring group in which the acyl group at the C-2 position of the sugar acts as a neighboring group and stabilizes a transient oxocarbenium ion. The1H NMR spectrum is identical to that obtained using ^^-glucosyl iodide 6 (Scheme 6, Example 4, FIG 6). Besides BF3• OEt2, glucosyl donor 17 can be activated by other Lewis acids, including FeCl3, TMSOTf, AgOTf, or Ag2O. Scheme 7. Glycosylation of CBN using ^^-D-glucose pentaacetate (17) Synthesis of CBN di- and tri-glycosides. In one embodiment of the current disclosure, the present inventors demonstrated the chemical synthesis of CBN di- and tri-glycosides. The glycosylation protocol's scope is extended to synthesize CBN di- and tri-glycosides 18–21 with readily available glycosyl donors 22–25 (Table 1, Examples 7–10). TABLE 1. CBN di- and tri-glycosides 16–20 from glycosyl donors 21–25 Yield Compound HPLC Product Glycosyl donor (two # (tR,min) steps) 18 57% 4.54 19 32% 4.59 20 44% 4.52 21 8% 4.34 Overview of the Synthesis of Cannabinoid Glucuronides. The study of drug and natural product metabolites contributes to our understanding of their toxicity, safety assessment, and biological activity. Glucuronides, a type of natural metabolite, are enzymatically formed during phase II metabolism in the liver. The glucuronidation of natural products (or aglycones) has been demonstrated to offer various benefits. These include enhanced solubility, which is particularly beneficial for hydrophobic drugs. Additionally, many glucuronides are pharmacologically active and can function as prodrugs. (Wadouachi et al., Molecules 2011, 16 (5), 3933; Stachulski et al., Nat Prod Rep 1998, 15, 173; Graaf et al., Curr Pharm Des 2002, 8 (15) 1391). CBD and CBN glucuronides, metabolites of CBD and CBN respectively, are formed by conjugating these cannabinoids with glucuronic acid. The chemical synthesis of these cannabinoid glucuronides, which could potentially benefit human health, is a relatively unexplored field (Zehavi et al., Chem Pharm Bull 1979, 27 (12), 3009; Watanabe et al., Carbohydrate Research, 1981, 98, 143). Synthesis of CBN-1-O-^^-D-glucuronide. In one embodiment of the current disclosure, the present inventors demonstrated the chemical synthesis of CBN-1-O-^^-D-glucuronide (27) and its salt 28. Scheme 8 outlines a synthetic strategy for CBN-1-O-^^-D-glucuronide (27). Adapting the Lewis acid-catalyzed glycosylation method used in Scheme 7, glucuronide 27 is prepared using glucuronide donor 26 in a two-step process involving glucuronidation and ester hydrolysis. Glucuronide 27 can then be converted into various salt forms. Scheme 8. Preparation of CBN-1-O-^^-D-glucuronide (27) and its salt 28 Synthesis of CBD-1’-O-^^-D-glucuronide. In one embodiment of the current disclosure, the present inventors demonstrated the chemical synthesis of CBD-1’-O-^^-D-glucuronide (32) and its salt 33. Scheme 9 presents a synthetic strategy for CBD-1’-O-^^-D-glucuronide (32). Employing the strategy used for the glucosylation of CBD (Schemes 1–2), O-TMS glucuronate iodide 30 is generated by treating per- O-TMS glucuronate 29 with TMSI. This is then reacted with CBD to yield CBD-1’-O-^^-D- glucuronide (32) after the deprotection of TMS groups. This can be converted to various salt forms to yield 33 using standard methods (Example 11). The glycosylation and glucuronidation methods detailed in Schemes 1–9, which utilize CBD and CBN as glycosylation and glucuronidation acceptors, can be adapted for the synthesis of glucosides and glucuronides of other cannabinoids, including CBG, CBC, THCV, THC, and others (See TABLE B: Exemplary Cannabinoid Glycosylation and Glucuronidation Sites). Scheme 10. Preparation of CBG-1’-O-^^-D-glucoside (36) and CBC-1’-O-^^-D-glucoside (37) using in situ generated ^^-glycosyl iodide 6 For instance, CBG and CBC, which contain a gem-dimethyl-substituted isoprenyl group, can be converted into the corresponding glycosides 36 and 37 under basic conditions using α- glucosyl iodide 6 in a manner similar to that described in Schemes 1–2 (Scheme 10). In contrast, for the preparation of THCV or THC glycosides 40 and 41, either α-glucosyl iodide 6 or β-D- glucose pentaacetate (17) can be employed as glucosyl donors, following procedures outlined in Schemes 1–2 and 7 (Scheme 11). Scheme 11. Preparation of THCV-1’-O-^^-D-glucoside (40) and THC-1’-O-^^-D-glucoside (41) using in situ generated ^^-glycosyl iodide 6 or ^^-D-glucose pentaacetate (17) Similarly, the synthesis of glucuronides of other cannabinoids can be achieved using the methods depicted in Schemes 8–9. For example, CBG and CBC can be converted into the corresponding glucuronides 42 and 43 under basic conditions with O-TMS glucuronate iodide 30 as the glucuronide donor (Scheme 12). Meanwhile, THCV and THC can be transformed into their respective glucuronides 44 and 45 using either O-TMS glucuronate iodide 30 or commercially available glucuronide donor 26, following similar conditions described in Schemes 8–9 (Scheme 13). Scheme 12. Preparation of CBG-1-O-^^-D-glucuronide (42) and CBC-1-O-^^-D-glucuronide (43)

[0006] Scheme 13. Preparation of THCV-1-O-^^-D-glucuronide (44) and THC-1-O-^^-D-glucuronide (45) Materials and Methods. All solvents and reagents were purchased from commercial sources and used without further purification unless otherwise noted. Reactions were monitored by TLC (thin layer chromatography) on 0.25 mm silica gel 60 F254 plates from MilliporeSigma using UV light, basic aqueous potassium permanganate (KMnO4), or iodine staining as the visualizing agent. EMD Millipore silica gel (60 Å, particle size 63–200 µm) was used for column chromatography. All NMR spectra were recorded at 300 K on Varian 300 MHz Mercury Plus spectrometer and were calibrated using residual undeuterated solvent as an internal reference. NMR data were processed using Mnova NMR processing software (Mestrelab Research S.L.). Analytical HPLC were performed on a Shimadzu 2050C using a Raptor ARC-18 column (100 mm x 4.6 mm x 5 µm) using a gradient with (1) acetonitrile with 0.1% formic acid and (2) water with 0.1% formic acid and 5 mM ammonium formate at a flow rate of 1.5 mL / min and detection was monitored at 220 nm. Example 1. Per-O-TMS ^^-D-glucose 4 This step was performed by adapting the literature procedures with modification (Bhat et al., Org Lett 2001, 3 (13), 2081–2084; and Wang et al., Carbohyd Res 2016, 427, 1–5; each of these is cited in the references). To a mixture of ^^-D-glucose (25.0 g, 0.139 mol) in DMF (400 mL) was treated with NEt3(107 mL, 0.763 mol) at 0 ˚C, followed by TMSCl (97 mL, 0.763 mol) at the same temperature. After stirring at rt over 12 h, the mixture was poured into ice-cold water (1000 mL) and the product portion was extracted with heptane (1200 mL). The organic layer separated, washed with satd. Na2SO4 solution (200 mL), brine (200 mL), dried (Na2SO4), filtered, and concentrated in vacuo to give crude product as yellow oil (69.93 g, 93%), which was used for the next step without purification. Example 2. Preparation of CBD-1’-O-^^-D-glucoside (3) Step A: Glycosylation of CBD using in situ generated TMS-protected α-D-glucose iodide 6. To a solution of TMS-protected glucose 4 (1858 mg, 3.43 mmol) in DCM (6.4 mL) was treated with TMSI (471 μL, 2.54 mmol) and the mixture was stirred at rt for 20 min. The complete conversion of ^^-iodide 5 to ^^-iodide 6 was determined by1H NMR analysis of the aliquot (sample preparation: about 20–40 μL of the aliquot taken from the mixture using 1 mL disposal syringe was dissolved in CDCl3). In a separate vial, CBD (400 mg, 1.27 mmol) and benzyltriethylammonium chloride (BTEAC) (434 mg, 1.91 mmol) were placed, and DCM (6.4 mL) and water (3 mL) were added. Then, the above TMS-protected ^^-iodide 7 in DCM was transferred into the vial containing CBD and BTEAC via a syringe. Subsequently, a solution of NaOH (305 mg, 7.63 mmol) in water (3 mL) was added. The mixture was flushed with argon and stirred at rt overnight. Upon completion, the mixture was diluted with DCM and the organic layer was separated. After washing with brine, the organic layer was dried (Na2SO4), filtered, and concentrated in vacuo. The crude was triturated with 10% EtOAc in hexane (10 mL X 3), filtered, washed (10% EtOAc in hexane), and concentrated in vacuo to give crude material. Purification of the crude by silica gel column chromatography (SiO25 g; hexane to 50% EtOAc in hexane) furnished 2a (657 mg, 68%) and 2b (110 mg, 12%). 2a:1H NMR (300 MHz, CDCl3) δ 6.44 (s, 2H), 5.97 (s, 1H), 5.56 (s, 1H), 4.57 (d, J = 7.2 Hz, 1H), 4.47 (s, 1H), 4.37 (s, 1H), 4.15 (d, J = 10.3 Hz, 1H), 3.73–3.64 (m, 2H), 3.59 (m, 1H), 3.50 – 3.37 (m, 2H), 3.07 (d, J = 9.1 Hz, 1H), 2.61–2.37 (m, 3H), 2.19 (s, 1H), 2.04 (d, J = 17.6 Hz, 1H), 1.85–1.71(m, 5H), 1.66 (s, 3H), 1.64 – 1.46 (m, 2H), 1.40–1.20 (m, 4H), 0.94 – 0.78 (m, 3H), 0.23 – 0.05 (m, 36H). Step B: Deprotection of TMS groups. To a solution of TMS protected CBD-1’-O-^^-D- glucoside 2a (294 mg, 0.38 mmol) in MeOH (5.5 mL) was added AcOH (220 μL, 3.84 mmol). After stirring for 4 h, the mixture was concentrated in vacuo and the residual acetic acid was removed by azeotrope with toluene (5 mL X 4). The crude was triturated with 2% MeOH in DCM (5 mL), filtered, washed with 1% MeOH in DCM (2 mL), and air-dried to give CBD-1’-O-^^-D- glucoside (3) (115 mg, 63%).1H NMR (300 MHz, CD3OD) δ 6.49 (d, J = 1.6 Hz, 1H), 6.29 (d, J = 1.6 Hz, 1H), 5.38–5.22 (m, 1H), 4.81–4.68 (m, 1H), 4.52 (d, J = 2.8 Hz, 1H), 4.46–4.36 (m, 1H), 4.14–3.98 (m, 1H), 3.90 (d, J = 12.1 Hz, 1H), 3.70 (dd, J = 12.1, 4.9 Hz, 1H), 3.53–3.35 (m, 4H), 3.14–2.92 (m, 1H), 2.45 (t, J = 7.7 Hz, 2H), 2.20 (s, 1H), 2.11–1.94 (m, 1H), 1.77 (m, 2H), 1.69 (s, 3H), 1.66–1.48 (m, 5H), 1.46–1.20 (m, 4H), 1.00–0.82 (m, 3H); HPLC, tR= 4.55 min. Example 3. Preparation of CBD-1’-O-^^-D-glucoside (3) in multi-gram scale In a 1 L flask, TMS protected glucose 4 (65.0 g, 120.2 mmol) was placed, and DCM (262 mL) was added. To the solution, TMSI (15.8 mL, 111.2 mmol) was added at rt dropwise for ~13 min under Ar. The mixture was stirred for about 15 min and the conversion of ^^-iodide 5 to ^^- iodide 6 was determined by1H NMR analysis of the aliquot of the mixture (total reaction time, 28 min). In a separate 1 L flask, CBD (14.0 g, 44.6 mmol) and BTEAC (15.2 g, 66.8 mmol) were placed, and water (114 mL) and DCM (84 mL) were added. The reaction flask was flushed with argon and the mixture was poured into the solution of TMS-protected ^^-D-glucose iodide 6 in the above. The reaction flask was washed with DCM (14 mL). Then, a solution of NaOH (10.6 g, 267.2 mmol in water (70 mL) was added for 3 min and the resulting mixture was stirred at rt for overnight (the color was changed from purple to pale yellow). Upon completion, the mixture was poured into a separate funnel. The organic layer was separated, and the aqueous layer was extracted with DCM (20 mL). The combined organic layers were washed with brine (200 mL), dried (Na2SO4), filtered, and concentrated in vacuo. To remove residual DCM, the crude was diluted with heptane (200 mL) and concentrated in vacuo. The resulting crude was diluted with 5% EtOAc in heptane (350 mL). After stirring for 20 min, the mixture was filtered, washed with 5% EtOAc in heptane (100 mL), and concentrated in vacuo. The crude was purified by short column chromatography (SiO2, 98 g; eluent, heptane to 50% EtOAc in heptane) to give 2a–b as a major product and 7 as a minor product (total combined products ~24 g, 71%). A mixture of 2a–b and 7 (~24 g, 31 mmol) was dissolved in MeOH (241 mL) and the mixture was stirred at rt for overnight. Upon completion, the mixture was concentrated in vacuo and the residue was diluted with EtOAc (100 mL). After concentration, the resulting residue was diluted with EtOAc (300 mL), and undissolved materials were removed by filtration and the cake was washed with EtOAc (100 mL). The combined filtrates were concentrated in vacuo and the crude was purified by column chromatography (SiO2, 318 g; Eluent, 70% EtOAc in hexane to 10% MeOH in EtOAc) to give CBD-1’-O-^^-D-glucoside (3) (13.7 g, 65%) and CBD-1,3’-di-O-^^-D- glucoside (8) (1 g, 3.5%). CBD-1’-O-^^-D-glucoside (3): HPLC, tR = 4.55 min. CBD-1,3’-di-O-^^-D-glucoside (8):1H NMR (300 MHz, CD3OD): δ 6.71 (m, 2H), 5.36 (s, 1H), 4.77 (m, 2H), 4.54 (s, 1H), 4.39 (s, , 4.18 (br d, J = 9.0, 1H), 3.88 (br d, J = 11.1 Hz, 2H), 3.67 (dd, J = 11.1, 4.8 Hz, 2H), 3.50- 3.32 (m, 8H), 3.13 (br q, J = 8.7 Hz, 1H), 2.53 (t, J = 7.8 Hz, 2H), 2.19 (br s, 1H), 2.00 (d, J = 16.8 Hz, 1H), 1.81-1.72 (m, 2H), 1.70 (s, 3H), 1.64-1.53 (m, 5H), 1.40-1.25 (m, 4H), 0.90 (t, J = 6.9 Hz, 3H).13C NMR (75 MHz, CD3OD) δ158.1 (2C), 150.2, 144.0, 134.2, 129.0, 122.5, 112.0, 111.0 (2C), 103.5 (2C), 78.3 (2C), 77.9 (2C), 75.3 (2C), 71.6 (2C), 62.7 (2C), 46.1, 38.4, 36.9, 32.7, 32.0, 31.8, 30.8, 23.7, 23.6, 19.9, 14.5; HPLC, tR = 2.93 min. Example 4: Preparation of CBN-1-O-^^-D-glucoside (13) and CBN-1-O-^^-D-glucoside (14) using O-TMS ^^-glucose iodide 6 The title compounds were prepared in a manner similar to that described in Example 5, using CBN as a glycosyl acceptor. Briefly, CBN (2.16 g, 6.96 mmol) and BTEAC (2.41 g, 10.6 mmol) were placed, and water (21.3 mL) was added, followed by dichloromethane (8.06 mL). The above solution was poured into the in situ generated ^^-iodide 6 (10.2 g,17.7 mmol) under an Ar atmosphere. Subsequently, a solution of sodium hydroxide (1.62 g, 40.5 mmol) was added in water (7.90 mL). The mixture was flushed with Ar and stirred at room temperature for 3 h. Upon completion, the organic layer was separated, and the aqueous layer was extracted with DCM (15 mL). The combined organic layers were washed with brine, dried (Na2SO4), filtered, and concentrated in vacuo. After concentration, the residue was diluted with heptane (40 mL) and concentrated in vacuo. To the residue, 20% iPrOAc in heptane (50 mL X 2) was added, the mixture was stirred for 20 min, filtered, and washed with 20% iPrOAc in heptane. The combined filtrates were concentrated in vacuo. The crude was purified by short column chromatography (SiO2, 15 g; eluent, heptane to 5% iPrOAc in heptane) to yield a TMS protected CBN-1-O-D-glucoside (3.24 g, 61%), which was dissolved in MeOH (86 mL) and AcOH (438 mL, 7.66 mmol) was added. After stirring for 2 days, 4 M HCl (532 mL, 2.13 mmol, in dioxane) was added. The mixture was stirred for an additional 3 h. After concentration, the crude was purified by column chromatography (SiO2, 65 g; eluent, DCM to 5% MeOH in DCM) to furnish CBN-1-O-^^-D- glucoside (13) (995 mg, 50%) and CBN-1-O-^^-D-glucoside (14) (219 mg, 11%). CBN-1-O-^^-D-glucoside (13):1H NMR (300 MHz, CD3OD) δ 8.48 (d, J = 1.8 Hz, 1H), 7.14 (dd, J = 7.9, 1.8 Hz, 1H), 7.05 (dd, J = 7.9, 1.8 Hz, 1H), 6.74 (d, J = 1.7 Hz, 1H), 6.46 (d, J = 1.6 Hz, 1H), 5.17 (d, J = 7.7 Hz, 1H), 3.90 (dd, J = 12.0, 2.0 Hz, 1H), 3.71 (dd, J = 12.0, 5.2 Hz, 1H), 3.63 (td, J = 8.3, 1.5 Hz, 1H), 3.57–3.37 (m, 3H), 2.56 (t, J = 7.7 Hz, 2H), 2.36 (s, 3H), 1.73– 1.58 (pm, 2H), 1.55 (s, 3H), 1.52 (s, 3H), 1.37 (m, 4H), 0.92 (t, J = 6.0, 3H); HPLC, tR= 4.98 min. CBN-1-O-^^-D-glucoside (14):1H NMR (300 MHz, CD3OD) δ 8.59–8.51 (m, 1H), 7.14 (d, J = 7.9 Hz, 1H), 7.05 (ddd, J = 7.9, 1.8, 0.8 Hz, 1H), 6.86 (d, J = 1.6 Hz, 1H), 6.46 (d, J = 1.6 Hz, 1H), 5.72 (d, J = 3.6 Hz, 1H), 4.02 (dd, J = 9.7, 8.6 Hz, 1H), 3.74 – 3.65 (m, 3H), 3.59 (dt, J = 9.9, 3.4 Hz, 1H), 3.48 (dd, J = 9.9, 8.6 Hz, 1H), 2.55 (d, J = 8.6, 2H), 2.41 (s, 3H), 1.77–1.57 (m, 5H), 1.44 (s, 3H), 1.42–1.24 (m, 4H), 0.92 (t, J = 6.9 Hz, 3H); HPLC, tR= 4.96 min. Example 5: Preparation of CBN-1-O-^^-isomaltoside (16) The title compound 18 (222 mg) was obtained in two steps with a 35% yield, following a procedure similar to that outlined in Example 5, using CBN (0.4 g, 1.3 mmol) as a glycosyl acceptor and O-TMS ^^-glucose iodide 6 (0.9 g, 1.0 mmol) as a glycosyl donor.1H NMR (300 MHz, CD3OD) δ 8.50–8.44 (m, 1H), 7.14 (d, J = 7.9 Hz, 1H), 7.05 (ddd, J = 7.9, 1.7, 0.8 Hz, 1H), 6.70 (d, J = 1.6 Hz, 1H), 6.47 (d, J = 1.6 Hz, 1H), 5.22 (d, J = 7.7 Hz, 1H), 4.83 (d, J = 3.7 Hz, 1H), 4.13–4.04 (m, 1H), 3.80–3.69 (m, 3H), 3.69–3.58 (m, 6H), 3.57–3.51 (m, 1H), 3.39–3.34 (m, 1H), 2.59 (t, J = 7.8, 2H), 2.37 (s, 3H), 1.74–1.60 (m, 2H), 1.57 (s, 3H), 1.50 (s, 3H), 1.4–1.30 (m, 4H), 1.02–0.81 (m, 3H); HPLC, tR = 4.26 min. Example 6: Preparation of CBN-1-O-^^-D-glucoside (13) using ^^-D-glucose pentaacetate (17) CBN (13) (3.00 g, 9.66 mmol) and glucose pentaacetate 17 (3.77 g, 9.66 mmol) were added to a clean 40 mL vial. The solid mixture was dissolved in anhydrous DCM (30 mL) at 0 ˚C. Subsequently, NEt3 (0.673 mL, 4.83 mmol) was added to the cold mixture, followed by the slow addition of BF3 • OEt2 over 5 min. The reaction mixture was stirred for an hour at the same temperature. The mixture was then gradually allowed to room temperature and stirred for 16 h. Upon completion, the reaction mixture was diluted with DCM (100 mL) and washed twice with satd NaHCO3 (80 mL) and water. The organic layer was dried over anhydrous Na2SO4 and concentrated to obtain the crude product. The crude product was purified with column chromatography (SiO230 g, 1:1 iPrOAc and heptane) yield O-Acetate CBN-1-O-^^-D-glucoside (3.4 g, 71%) as a yellow oil. Next, O-Acetate CBN-1-O-^^-D-glucoside (3.30 g, 5.14 mmol), was dissolved in methanol at rt, and K2CO3(2.49 g, 18.0 mmol) was added to it. The mixture was stirred slowly at room temperature for 45 minutes. The solid was filtered off and the filtrate was concentrated using a rotary evaporator. The product was purified by flash column chromatography (SiO2 40 g, 5% MeOH / DCM) to yield the title compound 13 (2.23 g, 93%). The1H NMR spectrum is identical to that obtained from Example 4 (FIG 6); HPLC, tR= 4.98 min. Example 7: Preparation of CBN-1-O-^^-maltoside (18) The title compound 18 (2.3 g) was obtained in two steps with a 57% yield, following a procedure similar to that outlined in Example 6, using CBN (2.00 g, 6.44mmol) as a glycosyl acceptor and compound 22 (4.37g, 6.44 mmol) as a glycosyl donor.1H NMR (300 MHz, CD3OD) δ 8.46 (d, J = 1.7 Hz, 1H), 7.14 (d, J = 7.9 Hz, 1H), 7.09 – 6.98 (m, 1H), 6.73 (d, J = 1.6 Hz, 1H), 6.46 (d, J = 1.6 Hz, 1H), 5.23 (d, J = 3.8 Hz, 1H), 5.19 (d, J = 7.6 Hz, 1H), 3.99–3.76 (m, 4H), 3.76–3.57 (m, 5H), 3.48 (dd, J = 9.7, 3.8 Hz, 1H), 3.37–3.21 (m, 2H), 2.56 (t, J = 7.5, 2H), 2.36 (s, 3H), 1.72– 1.58 (m, 2H), 1.55 (s, 3H), 1.51 (s, 3H), 1.36 (m, 4H), 1.01–0.81 (m, 3H); HPLC, tR = 4.59 min; FIG 7 for the1H NMR spectrum of the title compound 18. Example 8: Preparation of CBN-1-O-^^-cellobioside (19) To a mixture of cellobiose octaacetate (2.20 g, 3.22 mmol) and CBN (1.00 g, 3.22 mmol) in anhydrous CH3CN (50 mL), NEt3(163 mg, 224 μL, 0.5 eq, 1.61 mmol) was added. Following this, a slow addition of BF3•OEt2(1.14 g, 1.02 mL, 2.5 eq, 8.05 mmol) was carried out, and the reaction temperature was raised to 50 °C and stirred for 16 h at the same temperature. Upon completion, the mixture was concentrated in vacuo. The residue was then dissolved in CH2Cl2(50 mL), and the organic layer was washed twice with saturated NaHCO3(80 mL), brine, dried (Na2SO4), filtered, and concentrated. The crude was purified by flash column chromatography (30 g SiO2; 1:1 iPrOAc and heptane) to furnish O-acetate CBN-1-O-^^-cellobioside (1.00 g, 34%). Next, O-acetate CBN-1-O-^^-cellobioside (500 mg, 0.500 mmol) was dissolved in CH3OH (20 mL), followed by the addition of K2CO3 (0.240 g, 3.5 eq, 1.76 mmol). The reaction was stirred for 45 min at rt. After concentration, the crude was purified by flash column chromatography (25 g SiO2; 10% CH3OH / CH2Cl2) to afford the title compound (301 mg, 95%). 1H NMR (300 MHz, CD3OD) δ 8.47 (d, J = 1.7 Hz, 1H), 7.14 (d, J = 7.9 Hz, 2H), 7.05 (dd, J = 7.9, 1.7 Hz, 2H), 6.71 (d, J = 1.6 Hz, 1H), 6.46 (d, J = 1.5 Hz, 1H), 5.21 (d, J = 7.2 Hz, 1H), 4.46 (d, J = 7.8 Hz, 1H), 3.99–3.83 (m, 2H), 3.77–3.57 (m, 6H), 3.46–3.14 (m, 2H), 2.56 (t, J = 7.8 Hz, 2H), 2.36 (s, 3H), 1.71–1.58 (m, 2H), 1.56 (s, 3H), 1.51 (s, 3H), 1.43–1.30 (m, 4H), 0.92 (t, J = 6.6 Hz, 3H); HPLC, tR = 4.59 min. Example 9: Preparation of CBN-1-O-^^-lactoside (20) The title compound 20 (1523 mg) was obtained in two steps with a 44% yield, following a procedure similar to that outlined in Example 6, using CBN (2.00g, 6.44 mmol) as a glycosyl acceptor and compound 24 (4.37g, 6.44 mmol) as a glycosyl donor.1H NMR (300 MHz, CD3OD) δ 8.47 (d, J = 1.7 Hz, 1H), 7.14 (d, J = 7.9 Hz, 1H), 7.05 (dd, J = 7.9, 1.7 Hz, 1H), 6.71 (d, J = 1.6 Hz, 1H), 6.46 (d, J = 1.6 Hz, 1H), 5.27 – 5.15 (m, 1H), 4.41 (d, J = 7.5 Hz, 1H), 3.95–3.88 (m, 2H), 3.88–3.77 (m, 2H), 3.77 – 3.55 (m, 7H), 3.50 (dd, J = 9.7, 3.2 Hz, 1H), 2.56 (t, J = 7.5 Hz, 2H), 2.36 (s, 3H), 1.81–1.60 (m, 2H), 1.56 (s, 3H), 1.51 (s, 3H), 1.47–1.24 (m, 4H), 1.03–0.78 (m, 3H); HPLC, tR = 4.52 min. Example 10: Preparation of CBN-1-O-^^-maltotrioside (21) The title compound 21 (80 mg) was obtained in two steps with a 8% yield, following a procedure similar to that outlined in Example 6, using CBN (147 mg, 0.472 mmol) as a glycosyl acceptor and compound 25 (456 mg, 0.472 mmol) as a glycosyl donor.1H NMR (300 MHz, CD3OD) δ 8.46 (s, 1H), 7.14 (d, J = 7.9 Hz, 1H), 7.05 (d, J = 7.9 Hz, 1H), 6.73 (d, J = 1.6 Hz, 1H), 6.46 (d, J = 1.6 Hz, 1H), 5.24 (d, J = 3.8 Hz, 1H), 5.19 (d, J = 7.6 Hz, 1H), 5.16 (d, J = 3.8 Hz, 1H), 3.98 – 3.75 (m, 8H), 3.65 (m, 6H), 3.58 – 3.50 (m, 2H), 3.50 – 3.41 (m, 1H), 3.29-3.22 (m,1H), 2.56 (t, J = 7.6 Hz, 2H), 2.36 (s, 3H), 1.64 (m, 2H), 1.55 (s, 3H), 1.51 (s, 3H), 1.37 (m, 4H), 0.92 (t, J = 6.7 Hz, 4H); HPLC, tR= 4.34 min. FIG 8 for the1H NMR spectrum of the title compound 21. Example 11. Preparation of CBN-1-O-^^-D-glucuronide (27) and its arginine salt 28 A mixture of CBN (500 mg, 1.61 mmol) and methyl glucuronate tetraacetate (26) (610 mg, 1.61 mmol) was dissolved in DCM (15 mL). NEt3(0.12 mL, 0.81 mmol) was then added to the solution at 0 ˚C. This was followed by the slow addition of BF3 • OEt2 (0.510 mL, 4.03 mmol) over 5 min. The reaction mixture was stirred at 0 ˚C for an hour, then brought to rt and stirred for additional 16 h. The reaction was monitored by TLC. Upon completion, the reaction mixture was diluted with DCM (50 mL). The organic layer was washed twice with satd NaHCO3 (70 mL) and water. The organic layer was dried over anhydrous Na2SO4 and concentrated to obtain the crude product. The crude product was purified with column chromatography (1:2 iPrOAc and heptane) to yield protected CBN-1-O-^^-D-glucuronide (550 mg, 89%). The ester hydrolysis and acetate deprotection were carried out in a single step by dissolving the protected glucuronide (250 mg, 0.400 mmol) in a mixture of 1 M NaOH (6 mL), and MeOH (9 mL). The reaction mixture was stirred at rt for 24 h, followed by acidification using Dowex 50 (H+form) resin until the pH of the solution reached 2–3. The solvent was concentrated, and the product was purified by column chromatography (SiO225 g, 5% MeOH / DCM) to yield the title compound 27 (100 mg, 52%). HPLC, tR = 4.83 min. The salt formation was achieved by treating the solution of 27 (100 mg, 0.21 mmol) in MeOH (1.2 mL) with a solution of L-arginine (34 mg, 0.21 mmol) in water (1.2 mL) at rt. The mixture was stirred for 16 h, after which it was filtered and concentrated. White precipitates were obtained and thoroughly washed with iPrOAc, yielding the arginine salt 28 (122 mg, 90%). HPLC, tR= 4.83 min.

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Claims

CLAIMS What is claimed is:

1. A cannabinoid glycoside according to Formula (III):wherein: R1is ^^-D-glucopyranosyl-R3, ^^-D-glucopyranosyl-R3, ^^-D-galactopyranosyl-R3, ^^-D- galactopyranosyl-R3, or ^^-L-rhamnopyranosyl-R3; R2is linear alkane; R3is absent, -(1➝6)-^^-D-glucopyranoside, -(1➝4)-^^-D-glucopyranoside, -(1➝4)-^^-D- glucopyranosyl-(1➝4)-^^-D-glucopyranoside, -(1➝4)-^^-D-glucopyranosyl-(1➝4)-^^-D- glucopyranoside, or -(1➝6)-^^-D-glucopyranosyl-(1➝4)-^^-D-glucopyranoside; or a pharmaceutically acceptable salt thereof.

2. A cannabinoid glycoside according to Formula (I): wherein:R1is ^^-D-glucopyranosyl-R4, ^^-D-glucopyranosyl-R4, or ^^-D-galactopyranosyl-R4, ^^-D- galactopyranosyl-R4, or ^^-L-rhamnopyranosyl-R4; R2is H;R3is linear alkane; R4is absent, -(1➝6)-^^-D-glucopyranoside, -(1➝4)-^^-D-glucopyranoside, -(1➝4)-^^-D- glucopyranosyl-(1➝4)-^^-D-glucopyranoside, -(1➝4)-^^-D-glucopyranosyl-(1➝4)-^^-D- glucopyranoside, or -(1➝6)-^^-D-glucopyranosyl-(1➝4)-^^-D-glucopyranoside; or a pharmaceutically acceptable salt thereof.

3. A cannabinoid glycoside according to Formula (III): wherein:R1is a ^^-D-glucoside, ^^-isomaltoside, ^^-maltoside, ^^-lactoside, or ^^- maltotrioside, ^^-melibioside, ^^-rutinoside; ^^-cellotrioside; or ^^-panoside; R2is a linear alkane; or a pharmaceutically acceptable salt thereof.

4. A cannabinoid glycoside according to Formula (I): , wherein:R1is a ^^-D-glucoside, ^^-isomaltoside, ^^-maltoside, ^^-lactoside, or ^^- maltotrioside, ^^-melibioside, ^^-rutinoside; ^^-cellotrioside; or ^^-panoside; R2is H; R3is a linear alkane; or a pharmaceutically acceptable salt thereof.

5. A cannabinoid glycoside according of any of claims 1-4, wherein the linear alkane comprises a C5linear alkane.

6. A cannabinoid glycoside according to Formula (II): , or a pharmaceutically7. A cannabinoid glycoside according to Formula (IV): , or a pharmaceutically8. A cannabinoid glycoside according to Formula (V): , or a pharmaceutically9. A cannabinoid glycoside according to Formula (VI): (VI), or a pharmaceutically10. A cannabinoid glycoside according to Formula (VII): (VII), or a pharmaceutically11. A cannabinoid glycoside according to Formula (VIII): , or a12. A cannabinoid glycoside according to Formula (IX): ,or a pharmaceutically 13. A cannabinoid glycoside according to Formula (X): ,or a pharmaceutically acceptable salt thereof.

14. A cannabinoid glycoside according to Formula (XI): ,or a pharmaceutically acceptable salt thereof.

15. A cannabinoid glycoside according to Formula (XII): , or a16. A cannabinoid glycoside selected from: CBN-1-O-^^-glucoside; CBN-1-O-^^-isomaltoside; CBN-1-O-^^-maltoside; CBN-1-O-^^-lactoside; CBN-1-O-^^-maltotrioside, CBN-1-O-^^-melibioside; CBN-1-O-^^-rutinoside; CBN-1-O-^^-cellotrioside; CBN-1-O-^^-panoside; or CBN-1-O-^^-D-glucopyranosyl; CBN-1-O-^^-D-glucopyranosyl-(1➝6)-^^-D-glucopyranoside; CBN-1-O-^^-D-glucopyranosyl-(1➝4)-^^-D-glucopyranoside; CBN-1-O-^^-D-galactopyranosyl-(1➝4)-^^-D-glucopyranoside; CBN-1-O-^^-D-glucopyranosyl-(1➝4)-^^-D-glucopyranosyl-(1➝4)-^^-D-glucopyranoside; CBN-1-O-^^-D-galactopyranosyl-(1➝6)-^^-D-glucopyranoside; CBN-1-O-^^-L-rhamnopyranosyl-(1➝6)-^^-D-glucopyranoside; CBN-1-O-^^-D-glucopyranosyl-(1➝4)-^^-D-glucopyranosyl-(1➝4)-^^-D-glucopyranoside; CBN-1-O-^^-D-glucopyranosyl-(1➝6)-^^-D-glucopyranosyl-(1➝4)-^^-D-glucopyranoside; ora pharmaceutically acceptably salt of the same.

17. A cannabinoid glycoside selected from: CBD-1’-O-^^-glucoside; CBD-1’-O-^^-isomaltoside; CBD-1’-O-^^-maltoside; CBD-1’-O-^^-lactoside; CBD-1’-O-^^-maltotrioside; CBD-1’-O-^^-melibioside; CBD-1’-O-^^-rutinoside; CBD-1’-O-^^-cellotrioside; CBD-1’-O-^^-panoside; or a pharmaceutically acceptably salt of the same.

18. A cannabinoid glycoside selected from: CBD-1’-O-^^-D-glucopyranosyl; CBD-1’-O-^^-D-glucopyranosyl-(1➝6)-^^-D-glucopyranoside; CBD-1’-O-^^-D-glucopyranosyl-(1➝4)-^^-D-glucopyranoside; CBD-1’-O-^^-D-galactopyranosyl-(1➝4)-^^-D-glucopyranoside; CBD-1’-O-^^-D-glucopyranosyl-(1➝4)-^^-D-glucopyranosyl-(1➝4)-^^-D-glucopyranoside; CBD-1’-O-^^-D-galactopyranosyl-(1➝6)-^^-D-glucopyranoside; CBD-1’-O-^^-L-rhamnopyranosyl-(1➝6)-^^-D-glucopyranoside; CBD-1’-O-^^-D-glucopyranosyl-(1➝4)-^^-D-glucopyranosyl-(1➝4)-^^-D-glucopyranoside; CBD-1’-O-^^-D-glucopyranosyl-(1➝6)-^^-D-glucopyranosyl-(1➝4)-^^-D-glucopyranoside; or a pharmaceutically acceptably salt of the same.

19. A pharmaceutical composition comprising a therapeutically effective amount of the cannabinoid glycoside of any of claims 1-18, and a pharmaceutically acceptable carrier.

20. A method of synthesizing CBD-1’-O-^^-D-glucoside (3) and CBD-1’,3’-di-O-^^-D-glucoside (8) according to Scheme 2 as described herein.

21. A method of synthesizing a cannabidiol (CBD) glycoside, the method comprising: (a) reacting α-glucosyl iodide (6) with CBD under conditions to form O-TMS CBD-1’-O- ^^-D-glucoside (2) and O-TMS CBD-1’,3’-di-O-^^-D-glucoside (7); (b) deprotecting compounds 2 and 7 under conditions that form: CBD-1’-O-^^-D-glucoside (3) according to the formula (XIX): CBD-1’,3’- formula (XXI):

22. The method of claim 21,the CBD-1’-O-^^-D-glucoside (3) and / or the CBD-1’,3’-di-O-^^-D-glucoside (8).

23. The method of claim 21, wherein the step of reacting comprises reacting α-glucosyl iodide (6) with CBD in the presence of benzyltriethylammonium chloride (BTEAC), dichloromethane (DCM), water, and NaOH under a nitrogen atmosphere.

24. A method of synthesizing a CBD-1’,3’-di-O-^^-D-glucoside according to Scheme 4 as described herein.

25. A method of synthesizing a cannabidiol (CBD) glycoside, the method comprising:(a) reacting α-glucosyl iodide (6) under conditions that causes in situ anomerization forming ^^-glucosyl iodide (5); (b) reacting the glucosyl iodide (5) with CBD under conditions to form CBD-1’,3’-di-O- ^^-D-glucoside (9) according to the formula (II): .

26. The method of 25, wherein the (6) comprises the step ofreacting α-glucosyl iodide (6) with or (TBAI) to form ^^-glucosyl iodide (5) via in situ anomerization.

27. The method of 25, wherein the step of reacting glucosyl iodide (5) with CBD comprises the step of glucosyl iodide (5) with CBD in the presence of benzyltriethylammonium chloride (BTEAC), dichloromethane (DCM), water, NaOH, followed by the step of deprotection using methanol (MeOH) or acetic acid (AcOH) in MeOH.

28. A method of synthesizing a CBD-1-O-^^-D-glucose according to Scheme 5 as described herein.

29. A method of synthesizing a cannabidiol (CBD) glycoside, the method comprising: (a) reacting CBD with acetobromo-^^-D-glucose (10) under conditions that form CBD-1’- O-^^-D-glucoside (3) according to formula (XIX): .

30. The method of claim 29, wherein the step of reacting comprises the step of reacting CBD with acetobromo-^^-D-glucose (10) in the presence of benzyltriethylammonium chloride (BTEAC),dichloromethane (DCM), water, NaOH, followed by the step of deprotection using potassium carbonate (K2CO3) and methanol (MeOH).

31. The method of claim 29, wherein the step of reacting comprises the step of reacting CBD with acetobromo-^^-D-glucose (10) in the presence of K2CO3, water, tetrabutylammonium bromide (TBABr), MeOH and DCM.

32. A method of synthesizing CBN-1-O-^^-D-glucoside (13), and CBN-1-O-^^-D-glucoside (14) according to Scheme 6 as described herein.

33. A method of synthesizing a cannabinol (CBN) glycoside, the method comprising: (a) reacting CBN with ^^-glucosyl iodide (6) under conditions that form CBN-1-O-^^-D- glucoside (13) according to formula (XXIII): (XXIII), andCBN-1-O-^^-D- formula (IV): .

34. The method of claim 33,reacting CBN with ^^-glucosyl iodide (6) in the presence of benzyltriethylammonium chloride (BTEAC), dichloromethane (DCM), water, NaOH followed by the step of deprotection using acetic acid (AcOH) in MeOH and HCl in dioxane.

35. A method of synthesizing CBN-1-O-^^- isomaltoside (16) according to Scheme 6 as described herein.

36. A method of synthesizing a cannabinol (CBN) glycoside, the method comprising: (a) reacting CBN with ^^-isomaltosyl iodide (15) under conditions that form CBN-1-O-^^- isomaltoside (16) according to formula (V): .

37. The method of reacting CBN with ^^-isomaltosyl iodide (15) in the presence of benzyltriethylammonium chloride (BTEAC), dichloromethane (DCM), water, NaOH following by the step of deprotection using HCl in dioxane.

38. A method of synthesizing CBN-1-O-^^-D-glycoside according to Scheme 7 as described herein.

39. A method of synthesizing a cannabinol (CBN) glycoside, the method comprising: (a) reacting CBN with ^^-D-glucose pentaacetate (17) under conditions that form CBN-1- O-^^-D-glycoside according to formula (XXIII): .

40. The method of claim 39, wherein said step of reacting comprises reacting CBN with ^^-D- glucose pentaacetate (17) in the presence of a Lewis acid such as BF3 • OEt2, a base such as triethylamine (NEt3), a solvent such as DCM or CH3CN, followed by the step of deprotection using K2CO3, and MeOH.

41. The method of claim 40, wherein said Lewis acid is selected from BF3 • OEt2, FeCl3, TMSOTf, AgOTf, or Ag2O.

42. A method of synthesizing CBN di- and tri-glycoside according to a modified Scheme 7 as described herein.

43. A method of synthesizing a cannabinol (CBN) di- or tri-glycoside, the method comprising: (a) reacting CBN with a glycosyl donor selected from: , wherein the step ofCBN di- and tri-glycoside is selected from:.

44. The method of 43, wherein said step of reacting comprises reacting CBN with the ^^- glycosyl donor in the presence of benzyltriethylammonium chloride (BTEAC), dichloromethane (DCM), water, NaOH following by the step of deprotection using HCl in dioxane.

45. A method of synthesizing CBN-1-O-^^-D-glucuronide and its salt according to a Scheme 8 as described herein.

46. A method of synthesizing a cannabinol (CBN) glucuronide, the method comprising: (a) reacting CBN with a glucuronide donor (26) according to formula:wherein said step of reacting is under conditions that form CBN-1-O-^^-D-glucuronide (27) according to formula (XXIV): (XXIV),47. The method of claim 46, and further comprising reacting the CBN-1-O-^^-D-glucuronide (27) with an amino acid under conditions that form CBN-1-O-^^-D-glucuronate (28) salt according to Formula (XXV): (XXV).

48. The method of claim 46, wherein said step of reacting comprises reacting CBN with the glucuronide donor (26) in the presence of a Lewis acid such as BF3• OEt2, a base such as triethylamine (NEt3), a solvent such as DCM or CH3CN, followed by the step of deprotection using K2CO3, and MeOH.

49. The method of claim 48, wherein said Lewis acid is selected from BF3• OEt2, FeCl3, TMSOTf, AgOTf, or Ag2O.

50. The method of claim 47, wherein said step reacting the CBN-1-O-^^-D-glucuronide (27) with an amino acid comprises reacting CBN-1-O-^^-D-glucuronide (27) with arginine in the presence of MeOH and water.

51. A method of synthesizing CBD-1’-O-^^-D-glucuronide and its salt according to a Scheme 9 as described herein.

52. A method of synthesizing a cannabidiol (CBD) glucuronide, the method comprising: (a) reacting per-O-TMS glucuronate (29) with iodotrimethylsilane (TMSI) under conditions to form O-TMS glucuronate iodide (30); (b) reacting CBD with the O-TMS glucuronate iodide (30) under conditions to form an intermediate compound according to formula: (c) deprotecting theforming CBD-1’-O-^^-D- glucuronide according to Formula (XXVI): .

53. The method of claim 52, wherein CBD-1’-O-^^-D-glucuronide is converted into a CBD-1’-O- ^^-D-glucuronide salt according to formula (XXVII):(XXVII), wherein M is arginine or Na.

54. The method of claim 52, wherein the step of reacting comprising reacting CBD with the O- TMS glucuronate iodide (30) in the presence of BTEAC, water, DCM and NaOH.

55. The method of claim 52, wherein the step of deprotecting comprises reacting intermediate compound (31) with HCl or K2CO3 and MeOH.

56. The method of claim 53, wherein converting comprises reacting CBD-1’-O-^^-D-glucuronide with L-arginine and MeOH.

57. An isolated cannabinoid glycoside, cannabinoid glucuronide, or intermediate compound synthesized by the method of any of claims 20-56.

58. A pharmaceutical composition comprising a cannabinoid glycoside, cannabinoid glucuronide, or intermediate compound synthesized by the method of any of claims 20-56, and a pharmaceutically acceptable carrier.

59. A cannabinoid glycoside according to Formula (XIII):wherein R1is H, ^^-D-glucopyranosyl-R3, ^^-D-glucopyranosyl-R3, ^^-D-galactopyranosyl-R3, ^^-D- galactopyranosyl-R3, or ^^-L-rhamnopyranosyl-R3; R2is H; R3is absent, -(1➝6)-^^-D-glucopyranoside, -(1➝4)-^^-D-glucopyranoside, -(1➝4)-^^-D- glucopyranosyl-(1➝4)-^^-D-glucopyranoside, -(1➝4)-^^-D-glucopyranosyl-(1➝4)-^^-D- glucopyranoside, or -(1➝6)-^^-D-glucopyranosyl-(1➝4)-^^-D-glucopyranoside; or a pharmaceutically acceptable salt thereof.

60. A cannabinoid glycoside according to Formula (XIII): whereinR1is H, ^^-D-glucoside, ^^-isomaltoside, ^^-maltoside, ^^-lactoside, or ^^-maltotrioside, ^^- melibioside, ^^-rutinoside; ^^-cellotrioside; ^^-panoside; R2is H; or a pharmaceutically acceptable salt thereof.

61. A cannabinoid glycoside according to Formula (XIV): (XIV),or a pharmaceutically acceptable salt thereof.

62. A pharmaceutical composition comprising a therapeutically effective amount of the cannabinoid glycoside of any of claims 59-61, and a pharmaceutically acceptable carrier.

63. A method of synthesizing cannabigerol (CBG)-1’-O-^^-D-glucoside (36) according to Scheme 10 as described herein.

64. A method of synthesizing a CBG glycoside, the method comprising: (a) reacting α-glucosyl iodide (6) with CBG (34) to form O-TMS CBG-1’-O-^^-D- glucoside; (b) deprotecting O-TMS CBG-1’-O-^^-D-glucoside under conditions that form CBG-1’-O- ^^-D-glucoside (36) according to the formula (XIV): (XIV).

65. A method of claim 64, further comprising the step of isolating the CBG-1’-O-^^-D-glucoside (36).

66. The method of claim 64, wherein the step of reacting comprises reacting α-glucosyl iodide (6) with CBG in the presence of benzyltriethylammonium chloride (BTEAC), dichloromethane (DCM), water, and NaOH under a nitrogen atmosphere.

67. A method of synthesizing CBG-1’-O-^^-D-glucuronide according to a Scheme 12 as described herein.

68. A method of synthesizing a CBG glucuronide, the method comprising: (a) reacting CBG (34) with the O-TMS glucuronate iodide (30) under conditions to form CBG-1’-O-^^-D-glucuronide (42) according to Formula (XX):X).

69. The method of claim 68, further comprising the step of isolating the CBG-1’-O-^^-D- glucuronide (42).

70. The method of claim 68, wherein the step of reacting comprising deprotecting the reacted O- TMS glucuronate iodide (30).

71. The method of claim 70, wherein the step of deprotecting comprises reacting the O-TMS glucuronate iodide (30) that has been reacted with CBG with HCl or K2CO3and MeOH.

72. The method of claim 68, wherein the step of reacting comprising reacting CBG (34) with the O-TMS glucuronate iodide (30) in the presence of BTEAC, water, DCM and NaOH.

73. A cannabinoid glycoside according to Formula (XV): (XV), whereinR1is H, ^^-D-glucopyranosyl-R2, ^^-D-glucopyranosyl-R2, ^^-D-galactopyranosyl-R2, ^^-D- galactopyranosyl-R2, or ^^-L-rhamnopyranosyl-R2; R2is absent, -(1➝6)-^^-D-glucopyranoside, -(1➝4)-^^-D-glucopyranoside, -(1➝4)-^^-D- glucopyranosyl-(1➝4)-^^-D-glucopyranoside, -(1➝4)-^^-D-glucopyranosyl-(1➝4)-^^-D- glucopyranoside, or -(1➝6)-^^-D-glucopyranosyl-(1➝4)-^^-D-glucopyranoside;or a pharmaceutically acceptable salt thereof.

74. A cannabinoid glycoside according to Formula (XV): (XV), whereinR1is ^^-D-glucoside, ^^-isomaltoside, ^^-maltoside, ^^-lactoside, or ^^-maltotrioside, ^^- melibioside, ^^-rutinoside; ^^-cellotrioside; ^^-panoside;or a pharmaceutically acceptable salt thereof.

75. A cannabinoid glycoside according to Formula (XVI): , or a pharmaceutically76. A pharmaceutical composition comprising a therapeutically effective amount of the cannabinoid glycoside of any of claims 73-76, and a pharmaceutically acceptable carrier.

77. A method of synthesizing cannabichromene (CBC)-1’-O-^^-D-glucoside (37) according to Scheme 10 as described herein.

78. A method of synthesizing a CBC glycoside, the method comprising: (a) reacting α- glucosyl iodide (6) with CBC (35) to form O-TMS CBC-1’-O-^^-D- glucoside;(b) deprotecting O-TMS CBC-1’-O-^^-D-glucoside under conditions that form CBC-1’-O- ^^-D-glucoside (37) according to the formula (XVI): .

79. A method of claim the CBC-1’-O-^^-D-glucoside(37).

80. The method of claim 78, wherein the step of reacting comprises reacting α- glucosyl iodide (6) with CBC in the presence of benzyltriethylammonium chloride (BTEAC), dichloromethane (DCM), water, and NaOH under a nitrogen atmosphere.

81. A method of synthesizing CBC-1’-O-^^-D-glucuronide according to a Scheme 12 as described herein.

82. A method of synthesizing a CBC glucuronide, the method comprising: (a) reacting CBC (35) with the O-TMS glucuronate iodide (30) under conditions to form CBC-1’-O-^^-D-glucuronide (43) according to Formula (XXII): .

83. The method of claim 82, further comprising the step of isolating the CBC-1’-O-^^-D- glucuronide (43).

84. The method of claim 82, wherein the step of reacting comprising deprotecting the reacted O- TMS glucuronate iodide (30).

85. The method of claim 84, wherein the step of deprotecting comprises reacting the O-TMS glucuronate iodide (30) that has been reacted with CBC with HCl or K2CO3 and MeOH.

86. The method of claim 82, wherein the step of reacting comprising reacting CBC (35) with the O-TMS glucuronate iodide (30) in the presence of BTEAC, water, DCM and NaOH.

87. A cannabinoid glycoside according to Formula (XVII): (XVII), whereinR1is H, ^^-D-glucopyranosyl-R3, ^^-D-glucopyranosyl-R3, ^^-D-galactopyranosyl-R3, ^^-D- galactopyranosyl-R3, or ^^-L-rhamnopyranosyl-R3; R2is linear alkane; R3is absent, -(1➝6)-^^-D-glucopyranoside, -(1➝4)-^^-D-glucopyranoside, -(1➝4)-^^-D- glucopyranosyl-(1➝4)-^^-D-glucopyranoside, -(1➝4)-^^-D-glucopyranosyl-(1➝4)-^^-D- glucopyranoside, or -(1➝6)-^^-D-glucopyranosyl-(1➝4)-^^-D-glucopyranoside; or a pharmaceutically acceptable salt thereof.

88. A cannabinoid glycoside according to Formula (XVII):(XVII), wherein R1is ^^-D-glucoside, ^^-isomaltoside, ^^-maltoside, ^^-lactoside, or ^^-maltotrioside, ^^- melibioside, ^^-rutinoside; ^^-cellotrioside; ^^-panoside; R1is linear alkane; or a pharmaceutically acceptable salt thereof.

89. The cannabinoid glycoside of any of claims 87-88, wherein the linear alkane is n-propyl, or n- pentyl.

90. A cannabinoid glycoside according to Formula (XVIII): (XVIII),wherein R1is linear alkane selected from n-propyl, or n-pentyl; or a pharmaceutically acceptable salt thereof.

91. A pharmaceutical composition comprising a therapeutically effective amount of the cannabinoid glycoside of any of claims 87-90, and a pharmaceutically acceptable carrier.

92. A method of synthesizing tetrahydrocannabivarin (THCV)-1-O-^^-D-glucoside (40) according to Scheme 11 as described herein.

93. A method of synthesizing tetrahydrocannabinol (THC)-1-O-^^-D-glucoside (41) according to Scheme 11 as described herein.

94. A method of synthesizing a cannabinoid glycoside, the method comprising: (a) reacting α-glucosyl iodide (6) or β-D-glucose pentaacetate (17) with THCV (38) or THC (39) under conditions that form: THCV-1-O-^^-D-glucoside (40) according to the formula (XVIII): (XVIII),wherein R1 or THC-1-O-^^-D-glucoside (41) according to the formula (XVIII): (XVIII),wherein R1 is n-pentyl.

95. A method of claim 94, further comprising the step of isolating the THCV-1-O-^^-D-glucoside (40) or THC-1-O-^^-D-glucoside (41).

96. The method of claim 94, wherein the step of reacting comprises reacting α- glucosyl iodide (6) with THCV (38) or THC (39) in the presence of benzyltriethylammonium chloride (BTEAC), dichloromethane (DCM), water, and NaOH under a nitrogen atmosphere.

97. The method of claim 94, wherein said step of reacting comprises reacting THCV (38) or THC (39) with ^^-D-glucose pentaacetate (17) in the presence of a Lewis acid such as BF3 • OEt2, a base such as triethylamine (NEt3), a solvent such as DCM or CH3CN, followed by the step of deprotection using K2CO3, and MeOH.

98. The method of claim 97, wherein said Lewis acid is selected from BF3 • OEt2, FeCl3, TMSOTf, AgOTf, or Ag2O.

99. A method of synthesizing THCV-1-O-^^-D-glucuronide and / or THC-1-O-^^-D- glucuronide according to a Scheme 13 as described herein.

100. A method of synthesizing a cannabinoid glucuronide, the method comprising: (a) reacting THCV (38) or THC (39) with a glucuronide donor selected from: O-TMS glucuronate iodide (30) or methyl glucuronate tetraacetate (26) under conditions that form: THCV-1-O-^^-D-glucuronide (44) according to the formula (XXVIII):(XXVIII), wherein R1 is n-propyl; or THC-1-O-^^-D-glucuronide (45) according to the formula (XXVIII):(XXVIII), wherein R1 is n-pentyl.

101. A method of claim 100, further comprising the step of isolating the THCV-1-O-^^-D- glucuronide (44) or THC-1-O-^^-D-glucuronide (45).

102. The method of claim 100, wherein said step of reacting comprises reacting THCV (38) or THC (39) with the methyl glucuronate tetraacetate (26) in the presence of a Lewis acid, a base such as triethylamine (NEt3), a solvent such as DCM or CH3CN, followed by the step of deprotection using LIOH, and MeOH.

103. The method of claim 102, wherein said Lewis acid is selected from BF3• OEt2, FeCl3, TMSOTf, AgOTf, or Ag2O.

104. The method of claim 100, wherein the step of reacting comprising reacting THCV (38) or THC (39) with the O-TMS glucuronate iodide (30) in the presence of BTEAC, water, DCM and NaOH.

105. The method of claim 104, wherein the step of reacting comprising the step of deprotecting with HCl or K2CO3 and MeOH.

106. An isolated cannabinoid glycoside, cannabinoid glucuronide, or intermediate compound synthesized by the method of any of claims 63-72, 77-86, or 92-105.

107. A pharmaceutical composition comprising a cannabinoid glycoside, cannabinoid glucuronide, or intermediate compound synthesized by the method of any of claims 63-72, 77-86, or 92-105, and a pharmaceutically acceptable carrier.

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