115997-40-5

Upstream product

• 97390-18-6 1,6-anhydro-4-O-(4,6-O-benzylidene-β-D-glucopyranosyl)-2,3-O-(tetraisopropyldisiloxane-1,3-diyl)-β-D-glucopyranose 
• 104481-10-9 O-(2-O-benzoyl-3-O-benzyl-4,6-O-benzylidene-β-D-glucopyranosyl)-(1->4)-1,6-anhydro-β-D-glucopyranose 
• 97390-32-4 O-(3-O-benzyl-4,6-O-benzylidene-β-D-glucopyranosyl)-(1->4)-1,6-anhydro-2,3-O-(tetraisopropyldisiloxane-1,3-diyl)-β-D-glucopyranose 
• 104167-28-4 O-(2-O-benzoyl-3-O-benzyl-4,6-O-benzylidene-β-D-glucopyranosyl)-(1->4)-1,6-anhydro-2,3-O-(tetraisopropyldisiloxane-1,3-diyl)-β-D-glucopyranose 
• 100-39-0 benzyl bromide 
• 104481-11-0 O-(2-O-benzoyl-3-O-benzyl-4,6-O-benzylidene-β-D-glucopyranosyl)-(1->4)-1,6-anhydro-2-O-p-tolylsulfonyl-β-D-glucopyranose 

Downstream Products

• 104139-74-4 O-(2-O-benzoyl-3-O-benzyl-6-deoxy-β-D-xylo-hex-5-enopyranosyl)-(1->4)-1,6-anhydro-2-azido-3-O-benzyl-2-deoxy-β-D-glucopyranose 
• 104139-73-3 O-(2-O-benzoyl-3-O-benzyl-6-deoxy-6-iodo-β-D-glucopyranosyl)-(1->4)-1,6-anhydro-2-azido-3-O-benzyl-2-deoxy-β-D-glucopyranose 
• 115997-48-3 (2R,3S,4S,5R,6R)-6-((1R,2S,3R,4R,5R)-4-Azido-3-benzyloxy-6,8-dioxa-bicyclo[3.2.1]oct-2-yloxy)-5-benzoyloxy-4-benzyloxy-3-(2-chloro-acetoxy)-tetrahydro-pyran-2-carboxylic acid 
• 104139-77-7 O-(methyl 2-O-benzoyl-3-O-benzyl-4-O-chloroacetyl-α-L-idopyranosyluronate)-(1->4)-1,6-anhydro-2-azido-3-O-benzyl-2-deoxy-β-D-glucopyranose 
• 104139-72-2 O-(2-O-benzoyl-3-O-benzyl-6-O-p-tolylsulfonyl-β-D-glucopyranosyl)-(1->4)-1,6-anhydro-2-azido-3-O-benzyl-2-deoxy-β-D-glucopyranose 
• 104139-76-6 O-(2-O-benzoyl-3-O-benzyl-4-O-chloroacetyl-6-O-trityl-α-L-idopyranosyl)-(1->4)-1,6-anhydro-2-azido-3-O-benzyl-2-deoxy-β-D-glucopyranose 
• 104139-71-1 O-(2-O-benzoyl-3-O-benzyl-β-D-glucopyranosyl)-(1->4)-1,6-anhydro-2-azido-3-O-benzyl-2-deoxy-β-D-glucopyranose 
• 104139-75-5 O-(2-O-benzoyl-3-O-benzyl-α-L-idopyranosyl)-(1->4)-1,6-anhydro-2-azido-3-O-benzyl-2-deoxy-β-D-glucopyranose 
• 104139-79-9 (2R,3S,4S,5R,6R)-6-((2R,3S,4R,5R,6R)-2-Acetoxymethyl-5-azido-4,6-bis-benzyloxy-tetrahydro-pyran-3-yloxy)-5-benzoyloxy-4-benzyloxy-3-(2-chloro-acetoxy)-tetrahydro-pyran-2-carboxylic acid methyl ester 
• 104139-78-8 O-(methyl 2-O-benzoyl-3-O-benzyl-4-O-chloroacetyl-α-L-idopyranosyluronate)-(1->4)-1,6-di-O-acetyl-2-azido-3-O-benzyl-2-deoxy-D-glucopyranose 
• 104545-76-8 (2R,3S,4S,5R,6R)-6-((2R,3S,4R,5R)-2-Acetoxymethyl-5-azido-4-benzyloxy-6-bromo-tetrahydro-pyran-3-yloxy)-5-benzoyloxy-4-benzyloxy-3-(2-chloro-acetoxy)-tetrahydro-pyran-2-carboxylic acid methyl ester 
• 104139-81-3 (2R,3S,4S,5R,6R)-6-((2R,3S,4R,5R,6R)-2-Acetoxymethyl-5-azido-4,6-bis-benzyloxy-tetrahydro-pyran-3-yloxy)-5-benzoyloxy-4-benzyloxy-3-hydroxy-tetrahydro-pyran-2-carboxylic acid methyl ester 

Relevant academic research and scientific papers

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.