The synthesis of diosgenyl 2-amino-2-deoxy-#BETA#-D-glucopyranoside hydrochloride

摘要

The N-trifluoroacetyl-and N-tetrachlorophthaloyl-protected bromide of D-glucosamine has been used for the first time as a glycosyl donor for the glycosylation of diosgenin [(25R)-spirost-5-en-3#BETA#-ol].Both 1,3,4,6-tetra-O-acetyl-2-deoxy-2-trifluoroacetamido-#beta#-D-glucopyranoside and 1,3,4,6-tetra-O-acetyl-2-deoxy-2-tetrachlorophthalimido-#alpha#,#beta#-D-glucopyranoside were transformed into the approproliate glycosyl bromides. These reacted with diosgenin under mild conditions,using silver triflate as a promoter,and gave the glycosyl bromides. These reacted with diosgenin under mild conditions,using silver triflate as a promoter,and gave the corresponding protected diosgenyl glycosides. Each was deprotected to give diosgenyl 2-amino-2-deoxy-#beta#-D-glucopyranoside hydrochloride. The structures of the new glycosides were established by ~1H NMR spectroscopy.