Synthesis of the Four Configurational Isomers of<u>N</u>-Benzoyl-2, 3, 6-Trtdeoxy-3-<u>C</u>-Methyl-3-Amino-L-Hexose from the (2<u>S</u>, 3<u>R</u>)-Diol Obtained from α-Methylcinnamaldehyde by Fermentation with Baker'S Yeast

Abstract

Abstract The erythro and threo chiral C5 methyl ketones (4) and (5), prepared from the (2S, 3R)-methyl diel (1b), were converted into the phenylsulfenimines (6) and (7), which, in turn, on reaction with allyl-magnesiutn bromide, yielded after acid hydrolysis and benzoylation, the diastereoisomeric C8-N-aminodiol derivatives (9) and (11), with threo stereochemistry relative to positions 4 and 5. Ozonolysis of (9) and (11) yielded the l-arabino and l-xylo 3-O-methyl branched aminodeoxysugar derivatives (13) and (15), respectively. Using diallylzinc as the reagent, the diastereoisomeric erythro products (8) and (10) were obtained. The latter materials gave the l-ribo-and l-lyxo-(lL-vancosamine) derivatives (12) and (14) upon oxonolysis. The 1H and 13C NMR spectra of the four isomeric aminodeoxysugar derivatives (12)—(15) were discussed.