New Strategy for Synthesis of the Disaccharide Moiety of the Highly Potent Anticancer Natural Product OSW-1

Abstract

The facile synthesis of a partially protected OSW-1 disaccharide moiety, having a 2-O-p-methoxybenzoyl-β-D-xylopyranosyl-(1 → 3)-2-O-acetyl-L-arabinopyranoside structure, was elaborated by glycosylation in a β-stereoselective fashion. The xylopyranose donors were synthesized by a short synthetic approach via convenient selective 1,2-diacetal protection of 3,4-trans-diequatorial hydroxyl group. Regioselective ring opening of 1,2-diacetal-protected substrates efficiently led to the arabinopyranose acceptor with a free 3-hydroxyl group. Glycosylation of the xylopyranose donor with the arabinopyranose acceptor provided the β-disaccharide.

GRAPHICAL ABSTRACT

Keywords:

• Anticancer
• disaccharide
• OSW-1
• selective ring opening
• synthesis