87907-05-9

Basic information

• Product Name: (2S,3S,4S,5R,6R)-6-((2R,3S,4R,5R,6R)-4-Acetoxy-2-acetoxymethyl-5-azido-6-bromo-tetrahydro-pyran-3-yloxy)-4,5-bis-benzyloxy-3-(2-chloro-acetoxy)-tetrahydro-pyran-2-carboxylic acid methyl ester
• Synonyms: (2S,3S,4S,5R,6R)-6-((2R,3S,4R,5R,6R)-4-Acetoxy-2-acetoxymethyl-5-azido-6-bromo-tetrahydro-pyran-3-yloxy)-4,5-bis-benzyloxy-3-(2-chloro-acetoxy)-tetrahydro-pyran-2-carboxylic acid methyl ester
• CAS NO: 87907-05-9
• Molecular Weight: 799.026
• Mol File: 87907-05-9.mol

Chemical Properties

• CAS DataBase Reference: (2S,3S,4S,5R,6R)-6-((2R,3S,4R,5R,6R)-4-Acetoxy-2-acetoxymethyl-5-azido-6-bromo-tetrahydro-pyran-3-yloxy)-4,5-bis-benzyloxy-3-(2-chloro-acetoxy)-tetrahydro-pyran-2-carboxylic acid methyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: (2S,3S,4S,5R,6R)-6-((2R,3S,4R,5R,6R)-4-Acetoxy-2-acetoxymethyl-5-azido-6-bromo-tetrahydro-pyran-3-yloxy)-4,5-bis-benzyloxy-3-(2-chloro-acetoxy)-tetrahydro-pyran-2-carboxylic acid methyl ester(87907-05-9)
• EPA Substance Registry System: (2S,3S,4S,5R,6R)-6-((2R,3S,4R,5R,6R)-4-Acetoxy-2-acetoxymethyl-5-azido-6-bromo-tetrahydro-pyran-3-yloxy)-4,5-bis-benzyloxy-3-(2-chloro-acetoxy)-tetrahydro-pyran-2-carboxylic acid methyl ester(87907-05-9)

Safety Data

• Hazardous Substances Data: 87907-05-9(Hazardous Substances Data)

Upstream product

• 104530-54-3 (2S,3S,4S,5R,6R)-4,5-Bis-benzyloxy-3-(2-chloro-acetoxy)-6-((2R,3S,4R,5R)-4,6-diacetoxy-2-acetoxymethyl-5-azido-tetrahydro-pyran-3-yloxy)-tetrahydro-pyran-2-carboxylic acid methyl ester 
• 186967-38-4 3-O-acetyl-1,6-anhydro-2-azido-4-O-(tert-butyldimethylsilyl)-2-deoxy-β-D-glucopyranose 
• 88261-51-2 1,6-anhydro-2-azide-4-O-(tert-buthyldimethylsilyl)-2-deoxy-β-D-glucopyranose 
• 199792-17-1 C₂₃H₂₈O₆ 
• 48149-74-2 allyl D-glucopyranoside 
• 87326-68-9 3-O-acetyl-1,6-anhydro-2-azido-2-deoxy-β-D-glucopyranose 
• 67546-20-7 1,6-anhydro-2-azido-2-deoxy-β-D-glucopyranose 
• 139437-39-1 1,6-anhydro-2-deoxy-2-iodo-β-D-glucopyranose 
• 2873-29-2 D-glucal triacetate 
• 492-62-6 alpha-D-glucopyranose 
• 2280-44-6 D-Glucose 
• 604-68-2 α-D-glucopyranose peracetylate 
• 87907-02-6 O-(methyl 2,3-di-O-benzyl-4-O-(chloroacetyl)-β-D-glucopyranosyluronate)-(1->4)-3-O-acetyl-1,6-anhydro-2-azido-2-deoxy-β-D-glucopyranose 

Relevant articles and documents

PROCESS FOR PREPARING HEPARINOIDS AND INTERMEDIATES USEFUL IN THE SYNTHESIS THEREOF

Processes are disclosed for the synthesis of the Factor Xa anticoagulant fondaparinux and related compounds. Protected pentasaccharide intermediates and efficient and scalable processes for the industrial scale production of fondaparinux sodium by conversion of the protected pentasaccharide intermediates via a sequence of deprotection and sulfonation reactions are provided.

Synthesis of methyl glycoside derivatives of tri- and penta-saccharides related to the antithrombin III-binding sequence of heparin, employing cellobiose as a key starting-material.

Two key synthons for the title pentasaccharide derivative, methyl O-(methyl 2-O-benzoyl-3-O-benzyl-alpha-L-idopyranosyluronate)-(1----4)-6-O-acetyl- 2-azido - 3-O- benzyl-2-deoxy-beta-D-glucopyranoside and O-(methyl 2,3-di-O-benzyl-4-O- chloroacetyl-beta-D-glucopyranosyluronate)-(1----4)-3,6-di-O-acetyl-2-az ido-2- deoxy-alpha-D- glucopyranosyl bromide, were prepared from a common starting material, cellobiose. They were coupled to give a tetrasaccharide derivative that underwent O-dechloroacetylation to the corresponding glycosyl acceptor. Its condensation with the known 6-O-acetyl-2-azido-3,4-di-O-benzyl-2-deoxy-alpha-D-glucopyranosyl bromide afforded a 77% yield of suitably protected pentasaccharide, methyl O-(6-O- acetyl-2-azido-3,4-di-O-benzyl-2-deoxy-alpha-D-glucopyranosyl)-(1----4)- O- (methyl 2,3- di-O-benzyl-beta-D-glucopyranosyluronate)-(1----4)-O-(3,6-di-O-acetyl-2- azido-2 - deoxy-alpha-D-glucopyranosyl)-(1----4)-O-(methyl 2-O-benzoyl-3-O-benzyl-alpha-L- idopyranosyluronate)- (1----4)-6-O-acetyl-2-azido-3-O-benzyl-2-deoxy-beta-D-glucopyranoside. Sequential deprotection and sulfation gave the decasodium salt of methyl O-(2- deoxy-2-sulfamido-6-O-sulfo-alpha-D-glucopyranosyl)-(1----4)-O-(be ta-D- glucopyranosyl-uronic acid)-(1----4)-O-(2-deoxy-2-sulfamido-3,6-di-O-sulfo-alpha-D-gluco pyranosyl)- (1----4)-O-(2-O-sulfo-alpha-L-idopyranosyluronic acid)-(1----4)-2-deoxy-2- sulfamido-6-O- sulfo-beta-D-glucopyranoside (3). In a similar way, the trisaccharide derivative, the hexasodium salt of methyl O-(2-deoxy-2-sulfamido-6-O-sulfo-alpha-D- glucopyranosyl)- (1----4)-O-(beta-D-glucopyranosyluronic acid)-(1----4)-2-deoxy-2-sulfamido-3,6- di-O- sulfo-alpha-D-glucopyranoside (4) was synthesized from methyl O-(6-O-acetyl-2- azido- 3,4-di-O-benzyl-2-deoxy-alpha-D-glucopyranosyl)-(1----4)-O-(methyl 2,3-di-O- benzyl-beta- D-glucopyranosyluronate)-3,6-di-O-acetyl-2-azido-2-deoxy-alpha-D- glucopyranoside. The pentasaccharide 3 binds strongly to antithrombin III with an association constant almost equivalent to that of high-affinity heparin, but the trisaccharide 4 appears not to bind.