75336-65-1

Basic information

• Product Name: methyl 2,3,4-tris-O-(phenylmethyl)-α-D-glucopyranuorate
• Synonyms: methyl 2,3,4-tris-O-(phenylmethyl)-α-D-glucopyranuorate
• CAS NO: 75336-65-1
• Molecular Weight: 478.542
• Mol File: 75336-65-1.mol
• Article Data: 4

Chemical Properties

• CAS DataBase Reference: methyl 2,3,4-tris-O-(phenylmethyl)-α-D-glucopyranuorate(CAS DataBase Reference)
• NIST Chemistry Reference: methyl 2,3,4-tris-O-(phenylmethyl)-α-D-glucopyranuorate(75336-65-1)
• EPA Substance Registry System: methyl 2,3,4-tris-O-(phenylmethyl)-α-D-glucopyranuorate(75336-65-1)

Safety Data

• Hazardous Substances Data: 75336-65-1(Hazardous Substances Data)

Upstream product

• 102335-60-4 methyl uronate 
• 185380-12-5 methyl (allyl 2,3,4-tri-O-benzyl-β-D-glucopyranosid)uronate 
• 3082-96-0 methyl 1,2,3,4-tetra-O-acetyl-α,β-D-glucopyranosyluronate 
• 57820-69-6 (3R,4S,5S,6S)-2-bromo-6-(methoxycarbonyl)tetrahydro-2H-pyran-3,4,5-triyl triacetate 
• 141520-78-7 methyl (allyl β-D-glucopyranosid)uronate 
• 114663-53-5 methyl (allyl 2,3,4-tri-O-acetyl-β-D-glucopyranosid)uronate 
• 186581-53-3 diazomethane 
• 53008-65-4 methyl 2,3,4-tri-O-benzyl-D-glucopyranoside 
• 666238-59-1 methyl (allyl 2,3,4-tri-O-trimethylsilyl-β-D-glucopyranosid)uronate 
• 21085-72-3 1-bromo-2,3,4-tri-O-acetyl-α-D-glucuronic acid methyl ester 
• 125426-22-4 (allyl 2,3,4-tri-O-benzyl-α-D-glucopyranosid)uronic acid 
• 78184-40-4 1-O-allyl-2,3,4-tri-O-benzyl-α-D-glucopyranoside 

Downstream Products

• 80860-56-6 methyl uronate 
• 185380-40-9 (2S,3S,4S,5R,6R)-3,4,5-Tris-benzyloxy-6-((2R,3R,4S,5R,6S)-3,4,5,6-tetrakis-benzyloxy-tetrahydro-pyran-2-ylmethoxy)-tetrahydro-pyran-2-carboxylic acid methyl ester 
• 185380-38-5 (2S,3S,4S,5R,6S)-3,4,5-Tris-benzyloxy-6-((2R,3R,4S,5R,6S)-3,4,5,6-tetrakis-benzyloxy-tetrahydro-pyran-2-ylmethoxy)-tetrahydro-pyran-2-carboxylic acid methyl ester 
• 1693-80-7 6-O-(α-D-glucopyranosyluronic acid)-α,β-D-glucopyranose 
• 55610-71-4 methyl (methyl-2,3,4-tri-O-benzyl-α-D-glucopyranosid)uronate 
• 55610-74-7 (2S,3S,4S,5R,6R)-3,4,5-Tris-benzyloxy-6-methoxy-tetrahydro-pyran-2-carboxylic acid methyl ester 
• 75336-67-3 (2S,3S,4S,5R,6S)-3,4,5-Tris-benzyloxy-6-((2R,3R,4S,5R,6S)-3,4,5-tris-benzyloxy-6-methoxy-tetrahydro-pyran-2-ylmethoxy)-tetrahydro-pyran-2-carboxylic acid methyl ester 
• 75336-69-5 (2S,3S,4S,5R,6R)-3,4,5-Tris-benzyloxy-6-((2R,3R,4S,5R,6S)-3,4,5-tris-benzyloxy-6-methoxy-tetrahydro-pyran-2-ylmethoxy)-tetrahydro-pyran-2-carboxylic acid methyl ester 
• 75336-66-2 (2S,3S,4S,5R,6S)-3,4,5-Tris-benzyloxy-6-((2R,3R,4R,5R)-3,4,5-tris-benzyloxy-tetrahydro-furan-2-ylmethoxy)-tetrahydro-pyran-2-carboxylic acid methyl ester 
• 75336-68-4 (2S,3S,4S,5R,6S)-3,4,5-Tris-benzyloxy-6-((3aR,6R,7S,7aR)-6-benzyloxy-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-7-yloxy)-tetrahydro-pyran-2-carboxylic acid methyl ester 
• 80860-62-4 C₅₇H₇₈O₇ 
• 80860-62-4 C₅₇H₇₈O₇ 
• 80860-61-3 (2S,3S,4S,5R,6S)-3,4,5-Tris-benzyloxy-6-[(3S,8S,9S,10R,13R,14S,17R)-17-((R)-1,5-dimethyl-hexyl)-10,13-dimethyl-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-3-yloxy]-tetrahydro-pyran-2-carboxylic acid methyl ester 
• 80860-61-3 (2S,3S,4S,5R,6R)-3,4,5-Tris-benzyloxy-6-[(3S,8S,9S,10R,13R,14S,17R)-17-((R)-1,5-dimethyl-hexyl)-10,13-dimethyl-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-3-yloxy]-tetrahydro-pyran-2-carboxylic acid methyl ester 

Relevant articles and documents

Comparison of Several Glucuronate Glycosyl Donors

Methyl 3,4-di-O-benzyl-[(S)-1,2-O-(1-cyanoethylidene)]-α-D- glucopyranuronate (12), methyl 3,4-di-O-benzyl-[(S)-1,2-O-(1-ethoxyethylidene)]- α-D-glucopyranuronate (14), methyl 2-O-acetyl-3,4-di-O-benzyl-α-D- glucopyranuronate bromide (15), methyl (2-O-acetyl-3,4-di-O-benzyl-α-D- glucopyranosyl)uronate trichloroacetimidate (17), and methyl (2,3,4-tri-O-benzyl-α/β-D-glucopyranosyl)uronate trichloroacetimidate (30) were synthesized and used as glycosyl donors. Glycosylation reactions of 12 with (5-R)-2,3,4,5-tetrahydro-5-trityloxymethyl-2- furanone (32) and 14,15,17 with the corresponding (5-R)-2,3,4,5-tetrahydro-5- hydroxymethyl-2-furanone (31) provided the exclusively β-linked glucuronide 33 in 69%, 28%, 45%, and 71% yield, respectively. The coupling of donor 30 with acceptor 31 furnished the glucuronated lactone 35 in 70% yield with a surprisingly high content (20%) of the undesired α-linked sugar residue. The structure of 33 was proved by NMR and X-ray diffraction studies. In a model reaction a complete deprotection procedure of the glucuronic acid lactone conjugation was demonstrated.

The synthesis of glucuronides derived from the antidepressant drugs mianserin and Org 3770

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