87907-35-5

Basic information

• Product Name: methyl 2--3-O-benzyl-2-deoxy-α-D-glucopyranoside
• Synonyms: methyl 2--3-O-benzyl-2-deoxy-α-D-glucopyranoside
• CAS NO: 87907-35-5
• Molecular Weight: 417.459
• Mol File: 87907-35-5.mol
• Article Data: 5

Chemical Properties

• CAS DataBase Reference: methyl 2--3-O-benzyl-2-deoxy-α-D-glucopyranoside(CAS DataBase Reference)
• NIST Chemistry Reference: methyl 2--3-O-benzyl-2-deoxy-α-D-glucopyranoside(87907-35-5)
• EPA Substance Registry System: methyl 2--3-O-benzyl-2-deoxy-α-D-glucopyranoside(87907-35-5)

Safety Data

• Hazardous Substances Data: 87907-35-5(Hazardous Substances Data)

Upstream product

• 1078691-95-8 (+)-D-glucosamine hydrochloride 
• 77059-32-6 benzyl ((2S,3R,4R,5S,6R)-2,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-3-yl)carbamate 
• 141438-52-0 methyl 2--2-deoxy-4,6-O-(4-methoxybenzylidene)-α-D-glucopyranoside 
• 100-39-0 benzyl bromide 
• 93000-10-3 benzyl ((2R,4aR,6S,7R,8R,8aS)-8-hydroxy-6-methoxy-2-phenyl hexahydropyrano[3,2-d][1,3]dioxin-7-yl)carbamate 
• 4704-15-8 ((2S,3R,4R,5S,6R)-4,5-Dihydroxy-6-hydroxymethyl-2-methoxy-tetrahydro-pyran-3-yl)-carbamic acid benzyl ester 
• 60076-41-7 methyl 4,6-O-benzylidene-2-(benzyloxycarbonyl)amino-2-deoxy-α-D-glucopyranoside 
• 501-53-1 benzyl chloroformate 
• 3006-58-4 2-carbobenzyloxyamino-2-deoxy-D-glucopyranose 
• 93000-11-4 methyl 3-O-benzyl-4,6-O-benzylidene-2-(benzyloxycarbonyl)amino-2-deoxy-α-D-glucopyranoside 
• 141438-53-1 methyl 2--3-O-benzyl-2-deoxy-4,6-O-(4-methoxybenzylidene)-α-D-glucopyranoside 

Downstream Products

• 87907-36-6 methyl 6-O-benzoyl-3-O-benzyl-2-(benzyloxycarbonyl)amino-2-deoxy-α-D-glucopyranoside 
• 114869-95-3 methyl 6-O-acetyl-3-O-benzyl-2-benzyloxycarbonylamino-2-deoxy-α-D-glucopyranoside 
• 141438-55-3 methyl 2--3-O-benzyl-2,6-dideoxy-6-iodo-α-D-glucopyranoside 
• 117129-62-1 [(2S,3R,4R,5S,6R)-4-Benzyloxy-5-hydroxy-2-methoxy-6-(4-methoxy-phenoxymethyl)-tetrahydro-pyran-3-yl]-carbamic acid benzyl ester 
• 159489-36-8 Toluene-4-sulfonic acid (2R,3S,4R,5R,6S)-4-benzyloxy-5-benzyloxycarbonylamino-3-hydroxy-6-methoxy-tetrahydro-pyran-2-ylmethyl ester 
• 116386-34-6 methyl 3-O-benzyl-2-benzyloxycarbonylamino-6-O-chloroacetyl-2-deoxy-α-D-glucopyranoside 
• 286961-77-1 [(2S,3R,4R,6R)-4-Benzyloxy-6-(tert-butyl-dimethyl-silanyloxymethyl)-2-methoxy-5-oxo-tetrahydro-pyran-3-yl]-carbamic acid benzyl ester 
• 114869-97-5 methyl 6-O-acetyl-3-O-benzyl-2-benzyloxycarbonylamino-2-deoxy-4-O-(methyl 2-O-acetyl-3-O-benzyl-α-L-idopyranosyluronate)-α-D-glucopyranoside 
• 256348-54-6 [(2S,3R,4R,5S,6R)-4-Benzyloxy-5-((4aS,6S,7R,8R,8aR)-8-benzyloxy-7-hydroxy-2,2-dimethyl-hexahydro-pyrano[3,2-d][1,3]dioxin-6-yloxy)-6-hydroxymethyl-2-methoxy-tetrahydro-pyran-3-yl]-carbamic acid benzyl ester 
• 256348-55-7 Acetic acid (2R,3S,4R,5R,6S)-3-((2S,3R,4S,5R,6S)-3-acetoxy-4-benzyloxy-5-hydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxy)-4-benzyloxy-5-benzyloxycarbonylamino-6-methoxy-tetrahydro-pyran-2-ylmethyl ester 
• 256486-94-9 methyl 6-O-acetyl-4-O-[2-O-acetyl-3-O-(phenylmethyl)-α-L-idopyranuronosyl)-2-deoxy-2-[[(phenylmethoxy)carbonyl]amino]-3-O-(phenylmethyl)-α-D-glucopyranoside 
• 256348-53-5 Acetic acid (2R,3S,4R,5R,6S)-4-benzyloxy-5-benzyloxycarbonylamino-3-((2S,3R,4S,5R,6S)-3,5-diacetoxy-6-acetoxymethyl-4-benzyloxy-tetrahydro-pyran-2-yloxy)-6-methoxy-tetrahydro-pyran-2-ylmethyl ester 
• 256348-59-1 5-acetoxy-3-(6-acetoxymethyl-3-azido-4-benzyloxy-5-methoxy-tetrahydro-pyran-2-yloxy)-6-(2-acetoxymethyl-4-benzyloxy-5-benzyloxycarbonylamino-6-methoxy-tetrahydro-pyran-3-yloxy)-4-benzyloxy-tetrahydro-pyran-2-carboxylic acid methyl ester 

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Known 3-O-benzyl-1,2-O-isopropylidene-α-D-glucofuranose was first converted into methyl 3-O-benzyl-1,2-O-isopropylidene-β-L-idofuranuronate.Acid hydrolysis, followed by acetylation and treatment with titanium tetrabromide, gave methyl (2,4-di-O-acetyl-3-O-benzyl-α-L-idopyranosyl bromide)uronate, which was immediately transformed into methyl 4-O-acetyl-3-O-benzyl-β-L-idopyranuronate 1,2-(tert-butyl orthoacetate).A two-step replacement of the 4-O-acetyl by a 4-O-chloroacetyl group gave the key derivative, crystalline methyl 3-O-benzyl-4-O-chloroacetyl-β-L-idopyranuronate 1,2-(tert-butyl orthoacetate).Condensation of this orthoester with an excess of crystalline benzyl 6-O-acetyl-3-O-benzyl-2-(benzyloxycarbonyl)amino-2-deoxy-α-D-glucopyranoside in chlorobenzene in the presence of 2,6-dimethylpyridinium perchlorate gave crystalline benzyl 6-O-acetyl-3-O-benzyl-2-(benzyloxycarbonyl)amino-2-deoxy-4-O-(methyl 2-O-acetyl-3-O-benzyl-4-O-chloroacetyl-α-L-idopyranosyluronate)-α-D-glucopyranoside in 40 percent yield.O-Demonochloroacetylation, followed by condensation with known 3,6-di-O-acetyl-2-azido-4-O-benzyl-2-deoxy-α-D-glucopyranosyl bromide in dichloromethane in the presence of 2,4,6-trimethylpyridine, silver triflate, and molecular sieve provided benzyl O-(3,6-di-O-acetyl-2-azido-4-O-benzyl-2-deoxy-α-D-glucopyranosyl)-(1->4)-O-(methyl 2-O-acetyl-3-O-benzyl-α-L-idopyranosyluronate)-(1->4)-6-O-acetyl-3-O-benzyl-2-(benzyloxycarbonyl)amino-2-deoxy-α-D-glucopyranoside in 88 percent yield.O-Deacetylation with sodium hydroxide, followed successively by O-sulfation in N,N-dimethylformamide in the presence of sulfur trioxide-trimethylamine complex, catalytic hydrogenolysis, and N-sulfation in water with the same sulfating agent, gave the heptasodium salt of O-(2-deoxy-2-sulfamido-3,6-di-O-sulfo-α-D-glucopyranosyl)-(1->4)-O-(2-O-sulfo-α-L-idopyranosyluronic acid)-(1->4)-2-deoxy-2-sulfamido-6-O-sulfo-D-glucopyranose.This trisaccharide, which is a fragment of the minimal antithrombin III-binding region in heparin, neither binds to antithrombin III nor induces anti-Xa activity.