92955-24-3

Basic information

• Product Name: methyl 6-O-benzoyl-3-O-benzyl-2-(benzyloxycarbonyl)amino-2-deoxy-4-O-(methyl 2,4-di-O-acetyl-3-O-benzyl-α-L-idopyranosyluronate)-α-D-glucopyranoside
• CAS NO: 92955-24-3
• Molecular Weight: 885.919
• Mol File: 92955-24-3.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: methyl 6-O-benzoyl-3-O-benzyl-2-(benzyloxycarbonyl)amino-2-deoxy-4-O-(methyl 2,4-di-O-acetyl-3-O-benzyl-α-L-idopyranosyluronate)-α-D-glucopyranoside(CAS DataBase Reference)
• NIST Chemistry Reference: methyl 6-O-benzoyl-3-O-benzyl-2-(benzyloxycarbonyl)amino-2-deoxy-4-O-(methyl 2,4-di-O-acetyl-3-O-benzyl-α-L-idopyranosyluronate)-α-D-glucopyranoside(92955-24-3)
• EPA Substance Registry System: methyl 6-O-benzoyl-3-O-benzyl-2-(benzyloxycarbonyl)amino-2-deoxy-4-O-(methyl 2,4-di-O-acetyl-3-O-benzyl-α-L-idopyranosyluronate)-α-D-glucopyranoside(92955-24-3)

Safety Data

• Hazardous Substances Data: 92955-24-3(Hazardous Substances Data)

Upstream product

• 87907-34-4 methyl 3-O-benzyl-4,6-O-benzylidene-2-(benzyloxycarbonyl)amino-2-deoxy-α-D-glucopyranoside 
• 60076-41-7 methyl 4,6-O-benzylidene-2-(benzyloxycarbonyl)amino-2-deoxy-α-D-glucopyranoside 
• 93382-47-9 methyl (acetyl 2,4-di-O-acetyl-3-O-benzyl-α,β-L-idopyranoside)uronate 
• 87907-09-3 methyl 3-O-benzyl-4-O-monochloroacetyl-β-L-idopyranuronate 1,2-(tert-butyl orthoacetate) 
• 87907-36-6 methyl 6-O-benzoyl-3-O-benzyl-2-(benzyloxycarbonyl)amino-2-deoxy-α-D-glucopyranoside 
• 87326-82-7 methyl 4-O-acetyl-3-O-benzyl-β-L-idopyranuronate 1,2-(tert-butyl orthoacetate) 
• 87327-03-5 methyl (2,4-di-O-acetyl-3-O-benzyl-α-L-idopyranosyl bromide)uronate 
• 87907-35-5 methyl 2--3-O-benzyl-2-deoxy-α-D-glucopyranoside 
• 100-39-0 benzyl bromide 
• 613-90-1 benzoyl cyanide 
• 87326-81-6 methyl 4-O-acetyl-3-O-benzyl-β-L-idopyranuronate 1,2-(methyl orthoacetate) 
• 108-24-7 acetic anhydride 
• 92955-25-4 methyl 6-O-benzoyl-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 

Relevant articles and documents

SYNTHESIS OF HEPARIN FRAGMENTS. A CHEMICAL SYNTHESIS OF THE TRISACCHARIDE O-(2-DEOXY-2-SULFAMIDO-3,6-DI-O-SULFO-α-D-GLUCOPYRANOSYL)-(1->4)-O-(2-O-SULFO-α-L-IDOPYRANOSYL-URONIC ACID)-(1->4)-2-DEOXY-2-SULFAMIDO-6-O-SULFO-D-GLUCOPYRANOSE HEPTASODIUM SALT

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.