Stereochemical Studies. XLVIII. Stereoselective Synthesis of 6-Deoxy-L-hexose Derivatives from L-Alanine without a Resolution Step

A new stereoselective synthesis of methyl α-L-amicetoside (11), methyl α-L-mycaminoside (14) and methyl α-L-oleandroside (17) starting from L-alanine is described. It is shown that methyl 2, 3, 6-trideoxy-α-L-hex-2-enopyranosid-4-ulose (8) is readily accessible from L-alanine in optically pure state and is a potential intermediate for the synthesis of various kinds of 6-deoxy-L-hexoses.