444118-41-6

Basic information

• Product Name: methyl 3-O-benzyl-1,2-O-isopropylidene-α-D-glucopyranosiduronate
• Synonyms: methyl 3-O-benzyl-1,2-O-isopropylidene-α-D-glucopyranosiduronate
• CAS NO: 444118-41-6
• Molecular Weight: 338.357
• Mol File: 444118-41-6.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: methyl 3-O-benzyl-1,2-O-isopropylidene-α-D-glucopyranosiduronate(CAS DataBase Reference)
• NIST Chemistry Reference: methyl 3-O-benzyl-1,2-O-isopropylidene-α-D-glucopyranosiduronate(444118-41-6)
• EPA Substance Registry System: methyl 3-O-benzyl-1,2-O-isopropylidene-α-D-glucopyranosiduronate(444118-41-6)

Safety Data

• Hazardous Substances Data: 444118-41-6(Hazardous Substances Data)

Upstream product

• 116-11-0 2-Methoxypropene 
• 13265-84-4 D-glucal 
• 106445-04-9 1-(6-benzyloxy-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-5-yl)-2-(tert-butyldimethylsiloxy)ethanol 
• 87326-73-6 (S)-methyl 2-((3aR,5R,6S,6aR)-6-(benzyloxy)-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-5-yl)-2-hydroxyacetate 
• 87326-72-5 3-O-benzyl-1,2-O-isopropyridene-α-D-glucofuranuronic acid 
• 18685-18-2 3-O-benzyl-1,2-5,6-O-diisopropylidene-α-D-glucofuranose 
• 100-39-0 benzyl bromide 
• 22529-61-9 (1R)-1-((3aR,6S,6aR)-6-(benzyloxy)-2,2-dimethyltetrahydrofuro(2,3-d)(1,3)dioxol-5-yl)ethane-1,2-diol 
• 2873-29-2 D-glucal triacetate 
• 356067-93-1 3-O-benzyl-6-O-triisopropylsilyl-D-glucal 
• 137915-37-8 1,2-dideoxy-6-O-triisopropylsilyl-D-arabino-1-hexenopyranose 
• 177897-32-4 Acetic acid (R)-1-((3aR,5R,6S,6aR)-6-benzyloxy-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-yl)-2-(tert-butyl-dimethyl-silanyloxy)-ethyl ester 
• 177897-33-5 Acetic acid (R)-1-((3aR,5R,6S,6aR)-6-benzyloxy-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-yl)-2-hydroxy-ethyl ester 
• 582-52-5 1,2:5,6-di-O-isopropylidene-α-D-glucofuranose 

Downstream Products

• 444118-88-1 pent-4-enyl (methyl 2-O-acetyl-3-O-benzyl-4-O-tert-butyldimethylsilyl-α-L-idopyranosyluronate)-(1->4)-(6-O-acetyl-2-azido-3-O-benzyl-2-deoxy-α-D-glucopyranosyl)-(1->4)-methyl 3-O-benzyl-2-O-levulinoyl-β-D-glucopyranosyluronate 
• 444118-91-6 6-O-acetyl-2-azido-3,4-di-O-benzyl-2-deoxy-α-D-glucopyranosyl-(1->4)-methyl 3-O-benzyl-2-O-levulinoyl-β-D-glucopyranosyl-(1->4)-(3,6-di-O-acetyl-2-azido-2-deoxy-α/β-D-glucopyranosyl trichloroacetimidate 
• 444118-90-5 tert-butyldimethylsilyl (6-O-acetyl-2-azido-3,4-di-O-benzyl-2-deoxy-α-D-glucopyranosyl)-(1->4)-(methyl 3-O-benzyl-2-O-levulinoyl-β-D-glucopyranosyl)-(1->4)-3,6-di-O-acetyl-2-azido-2-deoxy-β-D-glucopyranoside 
• 444118-89-2 pent-4-enyl (methyl 2-O-acetyl-3-O-benzyl-α-L-idopyranosyluronate)-(1->4)-(6-O-acetyl-2-azido-3-O-benzyl-2-deoxy-α-D-glucopyranosyl)-(1->4)-methyl 3-O-benzyl-2-O-levulinoyl-β-D-glucopyranosyluronate 
• 444118-67-6 6-O-acetyl-2-azido-3-O-benzyl-4-O-tert-butyldimethylsilyl-2-deoxy-α-D-glucopyranosyl-(1->4)-methyl 2-O-levulinoyl-3-O-benzyl-α-D-glucopyranosyluronate trichloroacetimidate 
• 444118-62-1 tert-butyldimethylsilyl (6-O-acetyl-2-azido-3-O-benzyl-4-O-tert-butyldimethylsilyl-2-deoxy-α-D-glucopyranosyl)-(1->4)-methyl 3-O-benzyl-2-O-levulinoyl-β-D-glucopyranosyluronate 
• 444118-69-8 6-O-acetyl-2-azido-3,4-di-O-benzyl-2-deoxy-α-D-glucopyranosyl-(1->4)-methyl 3-O-benzyl-2-O-levulinoyl-α-D-glucopyranosyluronate trichloroacetimidate 
• 444118-75-6 pent-4-enyl (6-O-acetyl-2-azido-3-O-benzyl-4-O-tert-butyldimethylsilyl-2-deoxy-α-D-glucopyranosyl)-(1->4)-methyl 3-O-benzyl-2-O-levulinoyl-β-D-glucopyranosyluronate 
• 444118-65-4 tert-butyldimethylsilyl (6-O-acetyl-2-azido-3,4-di-O-benzyl-2-deoxy-α-D-glucopyranosyl)-(1->4)-methyl 3-O-benzyl-2-O-levulinoyl-β-D-glucopyranosyluronate 
• 444118-68-7 6-O-acetyl-2-azido-3-O-benzyl-4-O-tert-butyldimethylsilyl-2-deoxy-α-D-glucopyranosyl-(1->4)-methyl 2-O-allyloxycarbonyl-3-O-benzyl-α-D-glucopyranosyluronate trichloroacetimidate 
• 444118-63-2 tert-butyldimethylsilyl (6-O-acetyl-2-azido-3-O-benzyl-4-O-tert-butyldimethylsilyl-2-deoxy-α-D-glucopyranosyl)-(1->4)-methyl 2-O-allyloxycarbonyl-3-O-benzyl-β-D-glucopyranosyluronate 
• 444118-60-9 6-O-acetyl-2-azido-3-O-benzyl-4-O-tert-butyldimethylsilyl-2-deoxy-α-D-glucopyranosyl-(1->4)-methyl 3-O-benzyl-2-O-monochloroacetyl-α-D-glucopyranosyluronate trichloroacetimidate 
• 444118-79-0 pent-4-enyl (6-O-acetyl-2-azido-3-O-benzyl-4-O-tert-butyldimethylsilyl-2-deoxy-α-D-glucopyranosyl)-(1->4)-methyl 2-O-allyloxycarbonyl-3-O-benzyl-β-D-glucopyranosyluronate 
• 444118-64-3 tert-butyldimethylsilyl (6-O-acetyl-2-azido-3-O-benzyl-4-O-tert-butyldimethylsilyl-2-deoxy-α-D-glucopyranosyl)-(1->4)-methyl 3-O-benzyl-2-O-monochloroacetyl-β-D-glucopyranosyluronate 

Relevant articles and documents

One-pot conversion of glycals to cis-1,2-isopropylidene-α-glycosides

Described is a general method for the conversion of glycals to the corresponding 1,2-cis-isopropylidene-α-glycosides. Epoxidation of glycals with dimethyldioxirane followed by ZnCl2-catalyzed addition of acetone converted a variety of protected glycals into 1,2-cis-isopropylidene-α-glycosides in good yield. The reaction is compatible with a range of protecting groups, including esters, benzyl ethers, and silyl ethers, as well as free hydroxyl groups. This method has been applied to develop a synthesis of protected glucuronic acid 1, a key intermediate in the synthesis of glycosaminoglycans. Compound 1 was produced in seven steps and 32% overall yield.

Conformational locking of the glycosyl acceptor for stereocontrol in the key step in the synthesis of heparin

Complete control over the stereoselectivity of key coupling reactions in the synthesis of heparin can be exerted by conformationally locking the uronic acid acceptor (see scheme).