5-amino-5-deoxy-1-thioglucopyranosides - Synthesis of thioglycoside derivatives of nojirimycin

N-Benzyloxycarbonyl-protected 5-amino-5-deoxyglucofuranose derivative 1 cou ld be readily transformed into 6-O, N-carbonylidene nojirimycin 3 which aff orded the corresponding piperidinosyl trichloroacetimidate 6. This compound turned out to be a versatile piperidinosyl donor. Reaction with various me rcaptans as accepters in the presence of TMSOTf as catalyst gave 5-aza-1-th ioglucopyranosides 7a-c, 9, and 13 which were successfully deprotected.