PREPARATION AND REACTIVITY OF SOME 3-DEOXY-D-ALTRONIC ACID DERIVATIVES

Abstract

3-Amino-3-deoxy-2,4,5,6-tetra-O-methyl-D-altronic acid hydrochloride was the key intermediate in the preparation of poly[(2S,3R)-2-methoxy-3-(D-erythro-trimethoxypropyl)propanamide], a chiral nylon 3 analog. We now describe an alternative synthetic route to this amino acid and the unexpected reactivity of some of its 3-deoxy derivatives. Attempts to open the 3-azido-3-deoxy-tri-O-methyl (or O-benzyl)-D-altrono-1,5-lactone intermediates gave mixtures of products, mostly, α,β-unsaturated carbonyl compounds.

ACKNOWLEDGMENT

We thank the C.I.C.Y.T. (Comisión Interministerial de Ciencia y Tecnología) of Spain for financial support (Grant MAT99-0578-C02-01).