444118-40-5

Basic information

• Product Name: methyl 3-O-benzyl-1,2-O-isopropylidene-5-O-levulinoyl-β-L-idofuranosyluronate
• Synonyms: methyl 3-O-benzyl-1,2-O-isopropylidene-5-O-levulinoyl-β-L-idofuranosyluronate
• CAS NO: 444118-40-5
• Molecular Weight: 436.459
• Mol File: 444118-40-5.mol
• Article Data: 2

Chemical Properties

• CAS DataBase Reference: methyl 3-O-benzyl-1,2-O-isopropylidene-5-O-levulinoyl-β-L-idofuranosyluronate(CAS DataBase Reference)
• NIST Chemistry Reference: methyl 3-O-benzyl-1,2-O-isopropylidene-5-O-levulinoyl-β-L-idofuranosyluronate(444118-40-5)
• EPA Substance Registry System: methyl 3-O-benzyl-1,2-O-isopropylidene-5-O-levulinoyl-β-L-idofuranosyluronate(444118-40-5)

Safety Data

• Hazardous Substances Data: 444118-40-5(Hazardous Substances Data)

Upstream product

• 19856-23-6 levulinic acid Na-salt 
• 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 
• 87326-74-7 (S)-((3aR,5S,6S,6aR)-6-Benzyloxy-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-yl)-trifluoromethanesulfonyloxy-acetic acid methyl ester 
• 582-52-5 1,2:5,6-di-O-isopropylidene-α-D-glucofuranose 
• 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 
• 106445-04-9 1-(6-benzyloxy-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-5-yl)-2-(tert-butyldimethylsiloxy)ethanol 

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 
• 525593-61-7 pent-4-enyl (6-O-acetyl-2-azido-3-O-benzyl-2-deoxy-4-O-levulinoyl-β-D-glucopyranosyl)-(1->4)-(methyl 2-O-acetyl-3-O-benzyl-α-L-idopyranosyl)-(1->4)-6-O-acetyl-2-azido-3-O-benzyl-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 
• 525593-56-0 tert-butyldimethylsilyl (6-O-acetyl-2-azido-3-O-benzyl-2-deoxy-4-O-levulinoyl-α-D-glucopyranosyl)-(1->4)-methyl 2-O-acetyl-3-O-benzyl-β-L-idopyranosyluronate 
• 444118-74-5 6-O-acetyl-2-azido-3-O-benzyl-4-O-tert-butyldimethylsilyl-2-deoxy-α-D-glucopyranosyl-(1->4)-methyl 2-O-acetyl-3-O-benzyl-β-L-idopyranosyluronate trichloroacetimidate 
• 525593-55-9 tert-butyldimethylsilyl (6-O-acetyl-2-azido-3-O-benzyl-4-O-levulinoyl-2-deoxy-α-D-glucopyranosyl)-(1->4)-methyl 3-O-benzyl-β-L-idopyranosyluronate 
• 444118-73-4 3,6-di-O-acetyl-2-azido-4-O-tert-butyldimethylsilyl-2-deoxy-α-D-glucopyranosyl-(1->4)-methyl 2-O-acetyl-3-O-benzyl-β-L-idopyranosyluronate trichloroacetimidate 
• 525593-58-2 6-O-acetyl-2-azido-3-O-benzyl-2-deoxy-4-O-levulinoyl-α-D-glucopyranosyl-(1->4)-methyl 1,2-di-O-acetyl-3-O-benzyl-α/β-L-idopyranosyluronate 
• 444118-72-3 6-O-acetyl-2-azido-3-O-benzyl-4-O-tert-butyldimethylsilyl-2-deoxy-α-D-glucopyranosyl-(1->4)-methyl 1,2-di-O-acetyl-3-O-benzyl-L-idopyranosyluronate 
• 525593-53-7 6-O-acetyl-2-azido-3-O-benzyl-2-deoxy-4-O-levulinoyl-α-D-glucopyranosyl-(1->4)-methyl 3-O-benzyl-1,2-O-isopropylidene-β-L-idopyranosyluronate 
• 444118-71-2 3,6-di-O-acetyl-2-azido-4-O-tert-butyldimethylsilyl-2-deoxy-α-D-glucopyranosyl-(1->4)-methyl 1,2-di-O-acetyl-3-O-benzyl-α/β-L-idopyranosyluronate 
• 444119-10-2 methyl 1,2-di-O-acetyl-3-O-benzyl-4-O-tert-butyldimethylsilyl-α/β-L-idopyranosyluronate 
• 444119-08-8 methyl 3-O-benzyl-4-O-tert-butyldimethylsilyl-1,2-O-isopropylidene-β-L-idopyranosyluronate 

Relevant articles and documents

Toward the assembly of heparin and heparan sulfate oligosaccharide libraries: efficient synthesis of uronic acid and disaccharide building blocks

The monosaccharide moieties found in heparin (HP) and heparan sulfate (HS), glucosamine and two kinds of uronic acids, glucuronic and iduronic acids, were efficiently synthesized by use of glucosamine hydrochloride and glucurono-6,3-lactone as starting compounds. In the synthesis of the disaccharide building block, the key issues of preparation of uronic acids (glucuronic acid and iduronic acid moieties) were achieved in 12 steps and 15 steps, respectively, without cumbersome C-6 oxidation. The resulting monosaccharide moieties were utilized to the syntheses of HP/HS disaccharide building blocks possessing glucosamine-glucuronic acid (GlcN-GlcA) or iduronic acid (GlcN-IdoA) sequences. The disaccharide building blocks were also suitable for further modification such as glycosylation, selective deprotection, and sulfation.