100752-71-4

Upstream product

• 99571-46-7 2',3'-di-O-benzyl derivative of 1,6-anhydro-4',6'-O-benzylidenecellobiose 
• 99541-24-9 O-(2,3-di-O-benzyl-β-D-glucopyranosyl)-(1->4)-3-O-acetyl-1,6-anhydro-2-azido-2-deoxy-β-D-glucopyranose 
• 99541-22-7 O-(2,3-di-O-benzyl-4,6-O-benzylidene-β-D-glucopyranosyl)-(1->4)-1,6:2,3-dianhydro-β-D-mannopyranose 
• 99541-25-0 O-(2,3-di-O-benzyl-4-O-(chloroacetyl)-6-O-trityl-β-D-glucopyranosyl)-(1->4)-3-O-acetyl-1,6-anhydro-2-azido-2-deoxy-β-D-glucopyranose 
• 99541-23-8 O-(2,3-di-O-benzyl-4,6-O-benzylidene-β-D-glucopyranosyl)-(1->4)-3-O-acetyl-1,6-anhydro-2-azido-2-deoxy-β-D-glucopyranose 
• 135415-93-9 (1R,2S,3R,4R,5R)-4-Azido-2-((4aR,6S,7R,8S,8aR)-7,8-bis-benzyloxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-6-yloxy)-6,8-dioxa-bicyclo[3.2.1]octan-3-ol 

Downstream Products

• 99541-27-2 O-(6-O-acetyl-2-azido-3,4-di-O-benzyl-2-deoxy-α-D-glucopyranosyl)-(1->4)-O-(methyl 2,3-di-O-benzyl-β-D-glucopyranosyluronate)-(1->4)-3-O-acetyl-1,6-anhydro-2-azido-2-deoxy-β-D-glucopyranose 
• 100752-65-6 O-(2-azido-3,4-di-O-benzyl-2-deoxy-α-D-glucopyranosyl)-(1->4)-O-(methyl 2,3-di-O-benzyl-β-D-glucopyranosyluronate)-(1->4)-1,6-anhydro-2-azido-2-deoxy-β-D-glucopyranose 
• 100752-72-5 (2S,3S,4S,5R,6R)-3-((2R,3R,4R,5S,6R)-3-Azido-4,5-bis-benzyloxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxy)-6-((1R,2S,3R,4R,5R)-4-azido-3-hydroxy-6,8-dioxa-bicyclo[3.2.1]oct-2-yloxy)-4,5-bis-benzyloxy-tetrahydro-pyran-2-carboxylic acid 
• 99541-26-1 O-(methyl 2,3-di-O-benzyl-β-D-glucopyranosyluronate)-(1->4)-3-O-acetyl-1,6-anhydro-2-azido-2-deoxy-β-D-glucopyranose 
• 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 academic research and scientific papers

Synthesis, from cellobiose, of a trisaccharide closely related to the GlcNAc----GlcA----GlcN segment of the antithrombin-binding sequence of heparin.

O-(2-Deoxy-2-sulfamido-6-O-sulfo-alpha-D-glucopyranosyl)-(1----4)- O-(beta-D- glucopyranosyluronic acid)-(1----4)-1,6-anhydro-2-deoxy-2-sulfamido-6-O-sulfo-beta-D-gl ucopyranose pentasodium salt (14) was synthesized as a heparin-related oligosaccharide. The glycosyl acceptor (derived from cellobiose) and a glycosyl donor, 6-O-acetyl-2-azido-3,4-di-O-benzyl-2-deoxy-alpha-D-glucopyranosyl bromide, were coupled in the presence of mercuric bromide and molecular sieves 4A to afford a 69% yield of fully protected trisaccharide, namely, 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)-3-O-acetyl- 1,6-anhydro-2 - azido-2-deoxy-beta-D-glucopyranose (10), which was converted into the partially sulfated trisaccharide 14. Compound 10 also underwent acetolysis to afford the glycosyl acetate, for further elongation of the glycosyl chain.