CHEMICAL TRANSFORMATION OF A 1-DEOXYNOJIRIMYCIN DERIVATIVE INTO 1-DEOXYMANNOJIRIMYCIN AND 1-DEOXYGALACTOSTATIN

Treatment of utyldiphenylsilyl-1-5-dideoxy-1,5-imino-D-glucitol (4) wi th sodium hydride resulted in an intramolecular cyclization concomitan t with silyl migration, giving the carbamate derivative 5 in good yiel d. This was efficiently converted into 1-deoxymannojirimycin (2) via r egioselective p-toluenesulfonylation followed by an inversion reaction at the C-2 position. On the other hand, the monochloromethylsulfonate 10 obtained from 4 underwent configurational change at the C-4 positi on by the action of sodium benzoate. The resulting benzoate 11 was dep rotected to afford 1-deoxygalactostatin (3).