Synthesis of convicine (6-amino-5-β-D-glucopyranosyloxyuracil)

Abstract

Glycosidation of 6-acetamido-5-hydroxyuracil (1c) with tetra-O-acetyl-β-D-glucopyranosyl bromide gave the penta-acetate (1d), identical with the penta-acetate of natural convicine. Deacetylation of (1d) yielded the free glycoside, identical with convicine itself. In an alternative approach 1-benzylconvicine penta-acetate (8) was synthesised by a multi-step sequence from 5-tetrahydropyranyloxyuracil (2). Attempted debenzylation of compound (8) failed.