Synthesis of the Eight Configurational Isomers of N-Trifluoroacetyl-2-C-Methyl-2,3,6-Trideoxy-3-Amino-L-Hexcse from Non-Carbohydrate Precursors

Abstract

The erythro and threo chiral C₄-N, phenylsulfenimines (3) and (4), prepared from the (2S,3R)-methyl diol obtained in fermenting baker's yeast from cinnamaldehyde, were converted via reaction with BrMgCH₂ CH[dbnd]CHCH₃ and BrMgCH₂ CH[dbnd]CHCH₃/ZnCl₂, respectively, into the isomeria C₈-N adducts (5)², bearing relative stereochemistry at position 4 and 5 depending upon the reagent used. Ozonolysis of the terminal vinyl group of the N-trifluoroacetyl derivatives yielded, through the different addition experiments, the eight isomeric 2-C-methyl-2,3,6-trideoxy-3-amino-L-hexose derivatives (6) - (13).