Synthesis of glycosylrifamycins, a new type of semisynthetic rifamycins

Glycosylrifamycins, a new type of semisynthetic rifamycin derivatives, can be easily obtained by reaction of 3-(2-aminoethylthio)rifamycin SV (2) with a glycosyl compound carrying a coupling group, such as isothiocyanate or carboxy. We prepared O-acetylated and free glucopyranosyl and arabinopyranosyl derivatives of rifamycin S and SV (see 3-10). Additionally, derivatives with D-saccharo-1,4-lactone and with shikimic acid were obtained (see 11-15). Glycosylrifamycins show an interesting inhibitory power on Gram-positive bacteria (Table).