131083-67-5

Basic information

• Product Name: methyl 4-O-(2-acetamido-4,6-di-O-allyl-3-O-benzyl-2-deoxy-α-D-glucopyranosyl)-2,3-O-isopropylidene-aldehydo-L-iduronate dimethyl acetal
• CAS NO: 131083-67-5
• Molecular Weight: 667.751
• Mol File: 131083-67-5.mol

Chemical Properties

• CAS DataBase Reference: methyl 4-O-(2-acetamido-4,6-di-O-allyl-3-O-benzyl-2-deoxy-α-D-glucopyranosyl)-2,3-O-isopropylidene-aldehydo-L-iduronate dimethyl acetal(CAS DataBase Reference)
• NIST Chemistry Reference: methyl 4-O-(2-acetamido-4,6-di-O-allyl-3-O-benzyl-2-deoxy-α-D-glucopyranosyl)-2,3-O-isopropylidene-aldehydo-L-iduronate dimethyl acetal(131083-67-5)
• EPA Substance Registry System: methyl 4-O-(2-acetamido-4,6-di-O-allyl-3-O-benzyl-2-deoxy-α-D-glucopyranosyl)-2,3-O-isopropylidene-aldehydo-L-iduronate dimethyl acetal(131083-67-5)

Safety Data

• Hazardous Substances Data: 131083-67-5(Hazardous Substances Data)

Upstream product

• 131070-22-9 4-O-(2-acetamido-4,6-di-O-allyl-3-O-benzyl-2-deoxy-α-D-glucopyranosyl)-2,3-O-isopropylidene-aldehydo-L-idose dimethyl acetal 
• 131070-22-9 4-O-(2-acetamido-4,6-di-O-allyl-3-O-benzyl-2-deoxy-α-D-glucopyranosyl)-2,3-O-isopropylidene-aldehydo-D-glucose dimethyl acetal 
• 131070-16-1 4-O-(2-acetamido-2-deoxy-4,6-O-isopropylidene-α-D-gluco-pyranosyl)-2,3;5,6-di-O-isopropylidene-aldehydo-D-glucose dimethyl acetal 
• 89756-25-2 (4aR,6R,8R,8aS)-7-Amino-6-[(R)-((4S,5R)-5-dimethoxymethyl-2,2-dimethyl-[1,3]dioxolan-4-yl)-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-methoxy]-2,2-dimethyl-hexahydro-pyrano[3,2-d][1,3]dioxin-8-ol 
• 131070-23-0 4-O-(2-acetamido-4,6-di-O-allyl-3-O-benzyl-2-deoxy-α-D-glucopyranosyl)-5,6-di-O-acetyl-2,3-O-isopropylidene-aldehydo-L-idose dimethyl acetal 
• 131070-28-5 4-O-(2-acetamido-4,6-di-O-allyl-3-O-benzyl-2-deoxy-α-D-glucopyranosyl)-6-O-p-anisyldiphenylmethyl-2,3-O-isopropylidene-5-O-levulinoyl-aldehydo-L-idose dimethyl acetal 
• 131070-27-4 4-O-(2-acetamido-4,6-di-O-allyl-3-O-benzyl-2-deoxy-α-D-glucopyranosyl)-6-O-p-anisyldiphenylmethyl-2,3-O-isopropylidene-aldehydo-L-idose dimethyl acetal 
• 131070-24-1 4-O-(2-acetamido-4,6-di-O-allyl-3-O-benzyl-2-deoxy-α-D-glucopyranosyl)-2,3-O-isopropylidene-5,6-di-O-methanesulfonyl-aldehydo-D-glucose dimethyl acetal 
• 131070-29-6 4-O-(2-acetamido-4,6-di-O-allyl-3-O-benzyl-2-deoxy-α-D-glucopyranosyl)-2,3-O-isopropylidene-5-O-levulinoyl-aldehydo-L-idose dimethyl acetal 
• 131070-21-8 4-O-(2-acetamido-4,6-di-O-allyl-3-O-benzyl-2-deoxy-α-D-glucopyranosyl)-2,3;5,6-di-O-isopropylidene-aldehydo-D-glucose dimethyl acetal 
• 131070-18-3 4-O-(2-acetamido-3-O-benzyl-2-deoxy-4,6-O-isopropylidene-α-D-glucopyranosyl)-2,3;5,6-di-O-isopropylidene-aldehydo-D-glucose dimethyl acetal 
• 131070-15-0 4-O-(3-O-tert-butyldimethylsilyl-2-deoxy-4,6-O-isopropylidene-2-methoxyimino-α-D-arabino-hexopyranosyl)-2,3;5,6-di-O-isopropylidene-aldehydo-D-glucose dimethyl acetal 
• 131070-14-9 4-O-(3-O-tert-butyldimethylsilyl-2-deoxy-2-hydroxyimino-4,6-O-isopropylidene-α-D-arabino-hexopyranosyl)-2,3;5,6-di-O-isopropylidene-aldehydo-D-glucose dimethyl acetal 
• 131070-19-4 4-O-(2-acetamido-3-O-benzyl-2-deoxy-α-D-glucopyranosyl)-2,3;5,6-di-O-isopropylidene-aldehydo-D-glucose dimethyl acetal 

Downstream Products

• 131070-31-0 methyl uronate 
• 131070-31-0 methyl uronate 

Relevant articles and documents

Formation of disaccharides related to heparin and heparan sulfate by chemical modification of maltose

Maltose has been converted into 4-O-(2-amino-2-deoxy-α-D-glucopyranosyl)-L-idopyranuronic acid, 4-O-(2-amino-2-deoxy-α-D-glucopyranosyl)-D-glucopyranose, and 4-O-α-D-glucopyranosyl-L-idopyranose, the first two disaccharides being related structurally to biose sequences in heparin and heparan sulfate.Used as the starting material was a major product of the kinetic acetonation of maltose, namely, 2,3;5,6-di-O-isopropylidene-4-O-(4,6-O-isopropylidene-α-D-glucopyranosyl)-aldehydo-D-glucose dimethyl acetal.It was subjected to a sequence of transformations that included the introduction of a 2'-amino-2'-deoxy function into the glucosyl group, the inversion of C-5 in the glucose residue to give the L-ido configuration, oxidation at position 6, and cyclisation of the acyclic dimethyl acetal to give the desired pyranuronic acid.In the formation of the latter, the 5-O-levinoyl substituent was found to be less prone to acyl migration to O-6 than more conventional ester groups.The relative acid labilities of the O-isopropylidene and dimethyl acetal groups are compared, and conformations of the acyclic residues of some disaccharide derivatives are discussed.