1314746-14-9

Upstream product

• 171032-74-9 1,3,4,6-tetra-O-acetyl-2-azido-2-deoxy-D-glucopyranose 
• 66-99-9 β-naphthaldehyde 
• 589-15-1 1-bromomethyl-4-bromobenzene 
• 1314746-20-7 p-methylphenyl 2-azido-2-deoxy-4-O-(2-naphthylmethyl)-1-thio-D-glucopyranoside ⁽⁴⁾ 
• 1314746-19-4 C₂₂H₄₁N₃O₄SSi₃ 

Downstream Products

• 1314746-11-6 C₆₇H₇₄BrNO₁₅SSi 
• 1314746-09-2 1,6-anhydro-4-O-[2-azido-3-O-(4-bromobenzyl)-6-O-tert-butyldiphenylsilyl-2-deoxy-α-D-glucopyranosyl]-2-O-benzoyl-3-O-benzyl-β-L-idopyranose 
• 1314746-23-0 C₅₄H₅₈BrN₃O₁₂Si 
• 1314746-60-5 1,6-anhydro-4-O-(2-azido-3-O-benzoyl-6-O-tert-butyldiphenylsilyl-2-deoxy-4-O-(2-naphthylmethyl)-α-D-glucopyranosyl)-2-O-benzoyl-3-O-benzyl-β-L-idopyranose 
• 1314746-21-8 1,6-anhydro-4-O-[2-azido-6-O-tert-butyldiphenylsilyl-2-deoxy-4-O-(2-naphthylmethyl)-α-D-glucopyranosyl]-3-O-benzyl-β-L-idopyranose 
• 1361328-57-5 C₆₀H₆₆BrNO₁₂SSi 
• 1314746-17-2 C₄₉H₅₁N₃O₁₁Si 
• 1314746-22-9 6-O-acetyl-4-O-[2-azido-3-O-(4-bromobenzyl)-6-O-tert-butyldiphenylsilyl-2-deoxy-4-O-(2-naphthylmethyl)-α-D-glucopyranosyl]-2-O-benzoyl-3-O-benzyl-L-idopyranosyl acetate 
• 1314746-13-8 1,6-anhydro-4-O-[2-azido-3-O-(4-bromobenzyl)-6-O-tert-butyldiphenylsilyl-2-deoxy-4-O-(2-naphthylmethyl)-α-D-glucopyranosyl]-2-O-benzoyl-3-O-benzyl-β-L-idopyranose 
• 1334379-56-4 1-O-[2-azido-3-O-(4-bromobenzyl)-6-O-tert-butyldiphenylsilyl-2-deoxy-4-O-(2-naphthylmethyl)-α-D-glucopyranosyl]-2,4,5,6-tetra-O-benzyl-D-myo-inositol 
• 1334379-57-5 3-O-[2-azido-3-O-(4-bromobenzyl)-6-O-tert-butyldiphenylsilyl-2-deoxy-4-O-(2-naphthylmethyl)-α-D-glucopyranosyl]-2,4,5,6-tetra-O-benzyl-D-myo-inositol 

Relevant academic research and scientific papers

Synthesis of the heparin-based anticoagulant drug fondaparinux

Fondaparinux, a synthetic pentasaccharide based on the heparin antithrombin-binding domain, is an approved clinical anticoagulant. Although it is a better and safer alternative to pharmaceutical heparins in many cases, its high cost, which results from th

METHODS AND INTERMEDIATES FOR THE PREPARATION OF FONDAPARINUX

The present invention relates to methods for the synthesis of fondaparinux and intermediates thereto.

Synthesis of 3-O-sulfonated heparan sulfate octasaccharides that inhibit the herpes simplex virus type 1 host-cell interaction

Cell surface carbohydrates play significant roles in a number of biologically important processes. Heparan sulfate, for instance, is a ubiquitously distributed polysulfated polysaccharide that is involved, among other things, in the initial step of herpes simplex virus type 1 (HSV-1) infection. The virus interacts with cell-surface heparan sulfate to facilitate host-cell attachment and entry. 3-O-Sulfonated heparan sulfate has been found to function as an HSV-1 entry receptor. Achieving a complete understanding of these interactions requires the chemical synthesis of such oligosaccharides, but this remains challenging. Here, we present a convenient approach for the synthesis of two irregular 3-O-sulfonated heparan sulfate octasaccharides, making use of a key disaccharide intermediate to acquire different building blocks for the oligosaccharide chain assembly. Despite substantial structural differences, the prepared 3-O-sulfonated sugars blocked viral infection in a dosage-dependent manner with remarkable similarity to one another.