Towards a modular approach for heparin synthesis

Abstract

Trisaccharide 23 and sulfated disaccharide 28 have been prepared by a strategy whereby the glucuronic acid moieties were introduced at a late stage of a synthetic sequence by selective oxidation of primary hydroxy groups with TEMPO and NaOCl. During the oxidation step, the primary hydroxy groups of glucosamine moieties were efficiently protected as TBDPS ethers. The oxidation procedure and removal of the TBDPS groups proved to be compatible with the presence of sulfate esters.