162610-22-2

Upstream product

• 1186009-53-9 methyl 2,3,6-tri-O-benzyl-4-O-(4,6-O-benzylidene-2,3-di-O-methyl-α-L-idopyranosyl)-α-D-glucopyranoside 
• 74-88-4 methyl iodide 
• 1186009-49-3 methyl 2,3,6-tri-O-benzyl-4-O-(2-O-benzoyl-4,6-O-benzylidene-3-O-methyl-α-L-idopyranosyl)-α-D-glucopyranoside 
• 19488-48-3 methyl O-2,3,6-tri-O-benzyl-α-D-glucopyranoside 

Relevant academic research and scientific papers

An Efficient Modular One-Pot Synthesis of Heparin-Based Anticoagulant Idraparinux

Idraparinux is a fully O-sulfated α-methyl glycoside of heparin pentasaccharide motif known to interact with the antithrombin III domain and act as anticoagulant. The current most effective synthesis of Idraparinux is complicated and nonstereoselective, requiring numerous stepwise procedures with low yields. We report here an efficient modular one-pot synthesis of Idraparinux involving the use of a glycosyl phosphate with 6-O-tert-butyl diphenyl silyl group and a d-glucuronic acid-containing disaccharide thioglycoside with 6-O-acetyl group as donor building blocks for the α-directing one-pot glycosylations with an l-iduronic acid-containing disaccharide acceptor building block. The uronic acid was incorporated in a disaccharide module used in the one-pot synthesis to avoid the complicated late-stage installation of these acidic sugars. The one-pot synthesis of Idraparinux demonstrated here is an effective strategy and should be applicable to the modular assembly of other heparan sulfates with regiodefined sulfation pattern for functional study.

Process of preparation of L-iduronic acid comprising a decarboxylation/intramolecular cyclisation tandem reaction

The present invention relates to a process of preparation of L-iduronic acid and derivatives comprising a decarboxylation/intramolecular cyclisation tandem reaction. The present invention also relates to the intermediates of the process, as well as their use as intermediates in the preparation of Idraparinux.

PROCESS OF PREPARATION OF L-IDURONIC ACID AND DERIVATIVES COMPRISING A DECARBOXYLATION/INTRAMOLECULAR CYCLISATION TANDEM REACTION

The present invention relates to a process of preparation of L-iduronic acid and derivatives comprising a decarboxylation/intramolecular cyclisation tandem reaction. The present invention also relates to the intermediates of the process, as well as their use as intermediates in the preparation of Idraparinux.