185380-12-5

Basic information

• Product Name: methyl (allyl 2,3,4-tri-O-benzyl-β-D-glucopyranosid)uronate
• Synonyms: methyl (allyl 2,3,4-tri-O-benzyl-β-D-glucopyranosid)uronate
• CAS NO: 185380-12-5
• Molecular Weight: 518.607
• Mol File: 185380-12-5.mol
• Article Data: 2

Chemical Properties

• CAS DataBase Reference: methyl (allyl 2,3,4-tri-O-benzyl-β-D-glucopyranosid)uronate(CAS DataBase Reference)
• NIST Chemistry Reference: methyl (allyl 2,3,4-tri-O-benzyl-β-D-glucopyranosid)uronate(185380-12-5)
• EPA Substance Registry System: methyl (allyl 2,3,4-tri-O-benzyl-β-D-glucopyranosid)uronate(185380-12-5)

Safety Data

• Hazardous Substances Data: 185380-12-5(Hazardous Substances Data)

Upstream product

• 57820-69-6 (3R,4S,5S,6S)-2-bromo-6-(methoxycarbonyl)tetrahydro-2H-pyran-3,4,5-triyl triacetate 
• 3082-96-0 methyl 1,2,3,4-tetra-O-acetyl-α,β-D-glucopyranosyluronate 
• 100-39-0 benzyl bromide 
• 666238-59-1 methyl (allyl 2,3,4-tri-O-trimethylsilyl-β-D-glucopyranosid)uronate 
• 141520-78-7 methyl (allyl β-D-glucopyranosid)uronate 
• 21085-72-3 1-bromo-2,3,4-tri-O-acetyl-α-D-glucuronic acid methyl ester 
• 114663-53-5 methyl (allyl 2,3,4-tri-O-acetyl-β-D-glucopyranosid)uronate 

Downstream Products

• 185380-13-6 (2S,3S,4S,5R,6R)-6-Allyloxy-3,4,5-tris-benzyloxy-tetrahydro-pyran-2-carboxylic acid benzyl ester 
• 185380-88-5 (2S,3S,4S,5R,6S)-3,4,5-Tris-benzyloxy-6-[(2S,3S,4R,5S)-4-benzyloxy-2-benzyloxymethyl-5-((2S,3R,4S,5R)-2,3,5-tris-benzyloxy-tetrahydro-pyran-4-yloxy)-tetrahydro-furan-3-yloxy]-tetrahydro-pyran-2-carboxylic acid benzyl ester 
• 185380-50-1 (2S,3S,4S,5R,6S)-3,4,5-Tris-benzyloxy-6-((2R,3R,4S,5R,6R)-2,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-3-yloxy)-tetrahydro-pyran-2-carboxylic acid benzyl ester 
• 185380-59-0 (2S,3S,4S,5R,6S)-3,4,5-Tris-benzyloxy-6-((2R,3R,4S,5R,6R)-4,5,6-tris-benzyloxy-2-benzyloxymethyl-tetrahydro-pyran-3-yloxy)-tetrahydro-pyran-2-carboxylic acid benzyl ester 
• 185380-61-4 (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 benzyl ester 
• 185380-62-5 (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 benzyl ester 
• 185380-57-8 (2S,3S,4S,5R,6S)-3,4,5-Tris-benzyloxy-6-((2R,3R,4S,5R,6R)-2,3,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-4-yloxy)-tetrahydro-pyran-2-carboxylic acid benzyl ester 
• 185380-26-1 (2S,3S,4S,5R,6S)-3,4,5-Tris-benzyloxy-6-((2R,3R,4S,5R,6R)-2,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-3-yloxy)-tetrahydro-pyran-2-carboxylic acid methyl ester 
• 185380-34-1 (2S,3S,4S,5R,6S)-3,4,5-Tris-benzyloxy-6-((2R,3R,4S,5R,6R)-4,5,6-tris-benzyloxy-2-benzyloxymethyl-tetrahydro-pyran-3-yloxy)-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 
• 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 
• 185380-30-7 (2S,3S,4S,5R,6S)-3,4,5-Tris-benzyloxy-6-((2R,3R,4S,5R,6R)-2,3,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-4-yloxy)-tetrahydro-pyran-2-carboxylic acid methyl ester 
• 1693-80-7 6-O-(α-D-glucopyranosyluronic acid)-α,β-D-glucopyranose 
• 75336-65-1 methyl 2,3,4-tri-O-benzyl-α-D-glucopyranuronate 

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.