A Short and High Yield Access to Glycosyl Donors of Amino-Deoxy-Sugars of Biological Relevance

Abstract

Synthesis of silylglycosides of 3-azido-2-deoxy-L-arabino- and ribo-hexopyranoses 4 and 5 has been achieved in 3 steps and 44,6% and 18% overall yields, respectively. The corresponding N-trifluoroacetamido derivatives 9 and 10 were further prepared in 3 steps. Usefulness of 4,9, and 10 was demonstrated by coupling with epipodophyllotoxin derivatives or with suitably protected amino-acids such as serine or 4-OH-phenylglycine or 4-OH-phenylglycinyl glucoside.