1590422-07-3

Upstream product

• 1590422-06-2 methyl [2-O-acetyl-3-O-methyl-α-L-idopyranosyl]-(1→4)-2,3-di-O-benzyl-6-deoxy-6-C-(ethyl sulfonatomethyl)-α-D-glucopyranoside 
• 1590422-04-0 methyl [2-O-acetyl-4,6-O-(benzylidene)-3-O-methyl-α-L-idopyranosyl]-(1→4)-2,3-di-O-benzyl-6-deoxy-6-C-(ethyl sulfonatomethyl)-α-D-glucopyranoside 
• 1590421-89-8 methyl 2,3-di-O-benzyl-6-deoxy-6-C-(ethyl sulfonatomethyl)-α-D-glucopyranoside 
• 1591904-70-9 2-O-acetyl-4,6-O-(benzylidene)-3-O-methyl-L-idopyranosyl trichloroacetimidate 
• 1456718-87-8 methyl 2,3-di-O-benzyl-6-deoxy-6-C-(ethyl sulfonatomethyl)-4-O-(2'-naphthyl)methyl-α-D-glucopyranoside 
• 1590421-87-6 methyl 2,3-di-O-benzyl-6-deoxy-6-iodo-4-O-(2'-naphthyl)methyl-α-D-glucopyranoside 
• 856191-85-0 diazomethane diethyl ether 
• 291314-27-7 methyl 2,3-di-O-benzyl-4-O-(2-naphthyl)methyl-α-D-glucopyranoside 
• 1456719-00-8 C₁₈H₂₂O₈ 

Downstream Products

• 1590422-08-4 methyl [2,3-di-O-benzyl-4-O-(2'-naphthyl)methyl-6-deoxy-6-C-(ethyl sulfonatomethyl)-α-D-glucopyranosyl]-(1→4)-[methyl (2-O-acetyl-3-O-methyl-α-L-idopyranosyl)uronate]-(1→4)-2,3-di-O-benzyl-6-deoxy-6-C-(ethyl sulfonatomethyl)-α-D-glucopyranoside 

Relevant academic research and scientific papers

A modular synthetic approach to isosteric sulfonic acid analogues of the anticoagulant pentasaccharide idraparinux

Heparin-based anticoagulants are drugs of choice in the therapy and prophylaxis of thromboembolic diseases. Idraparinux is a synthetic anticoagulant pentasaccharide based on the heparin antithrombin-binding domain. In the frame of our ongoing research aimed at the synthesis of sulfonic acid-containing heparinoid anticoagulants, we elaborated a modular pathway to obtain a series of idraparinux-analogue pentasaccharides bearing one or two primary sulfonic acid moieties. Five protected pentasaccharides with different C-sulfonation patterns were prepared by two subsequent glycosylation reactions, respectively, using two monosaccharide and four disaccharide building blocks. Transformation of the protected derivatives into the fully O-sulfated, O-methylated sulfonic acid end-products was also studied.

Large-scale synthesis of 6-deoxy-6-sulfonatomethyl glycosides and their application for novel synthesis of a heparinoid pentasaccharide trisulfonic acid of anticoagulant activity

Multigram-scale syntheses of three 6-deoxy-6-sulfonatomethyl α-glucosides were accomplished via reactions of the corresponding primary triflate derivatives with the lithiated ethyl methanesulfonate. Chemoselective glycosylation reactions of different 6-C-sulfonatomethyl glucoside donors were studied. The sulfonic acid-containing building blocks were utilised in a novel [2+3] block synthesis of a trisulfonic acid isoster of the anticoagulant pentasaccharide idraparinux.