75336-65-1

Upstream product

• 102335-60-4 methyl uronate 
• 185380-12-5 methyl (allyl 2,3,4-tri-O-benzyl-β-D-glucopyranosid)uronate 
• 186581-53-3 diazomethane 
• 53008-65-4 methyl 2,3,4-tri-O-benzyl-D-glucopyranoside 
• 141520-78-7 methyl (allyl β-D-glucopyranosid)uronate 
• 114663-53-5 methyl (allyl 2,3,4-tri-O-acetyl-β-D-glucopyranosid)uronate 
• 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 
• 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 

Downstream Products

• 75336-62-8 Methyl 2,3,4-tri-O-benzyl-1-bromo-1-deoxy-D-glucopyranuronate 
• 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 
• 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 
• 185380-26-1 (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 
• 185380-30-7 (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 
• 75336-64-0 (2S,3S,4S,5R,6S)-3,4,5-Tris-benzyloxy-6-chloro-tetrahydro-pyran-2-carboxylic acid methyl ester 
• 75336-63-9 methyl <2,3,4-tri-O-benzyl-α-D-glucopyranosyl chloride>uronate 
• 165680-89-7 (2S,3S,4S,5R,6R)-3,4,5-Tris-benzyloxy-6-(diethoxy-phosphanyloxy)-tetrahydro-pyran-2-carboxylic acid methyl ester 
• 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 

Relevant academic research and scientific papers

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.

Stereoselective Syntheses of α-Glucuronides Using Dehydrative Glycosylation

Methyl and benzyl 2,3,4-tri-O-benzyl-D-glucopyranuronates, prepared from D-glucurono-6,3-lactone, afforded selectively the corresponding α-glucopyranosiduronates by the aid of the condensing reagent system composed of p-nitrobenzenesulfonyl chloride, silver trifluoromethanesulfonate, and triethylamine. Using this method, O-α-D-glucopyranuronosyl-(1→3)-O-α-L-arabinofuranosyl- (1→3)-D-xylopyranose, one of the minimal component units in the structure of plantago-mucilage A from the seeds of Plantago asiatica Linne constituting a Chinese medicine : chegianzi [HU~P].

Stereoselective glycosidations of uronic acids

Stereoselective glycosidation and disaccharide formation of uronic acids were performed with silver perchlorate in acetonitrile. The course of the reaction is controlled by intermediate nitrilium acetonitrile conjugates, which are generated in situ.