Studies on Aminosugars. XXXI. Synthesis of 3,4-Dideoxy-3-enosides and the Corresponding 3,4-Dideoxysugars

Abstract

Abstract As model experiments to prepare unsaturated and deoxy variants of complex aminoglycosidic antibiotics, methyl 3,4-dideoxy-α-d-erythro-hexopyranoside (8) and methyl 2,6-diamino-2,3,4,6-tetradeoxy-α-d-erythro-hexopyranoside (15) have been synthesized through the corresponding 3,4-unsaturated glycosides (6, 12), which were prepared from the corresponding 3,4-di-O-mesyl derivatives (5, 11) by treatment with sodium iodide and zinc dust in high yields. These are rare examples of 3,4-dideoxy and 3,4-unsaturated sugars.