Synthesis of 4-O-methyl-β-rhodomycins using derivatives of 4-amino-4-deoxy- and 3,4-diamino-3,4-dideoxy sugars

Abstract Synthesis of 7- O -(4-amino-2,4,6-trideoxy- and 7- O -(3,4-diamino-2,3,4,6-tetradeoxy-α- l - lyxo -hexopyranosyl)-4- O -methyl-β-rhodomycinones ( 31 and 33 ) are described. The glycosyl donors 2,4,6-trideoxy-1,3-di- O-p -nitrobenzoyl-4-trifluoroacetamido-β- l - lyxo -hexopyranose ( 14β ) and 2,3,4,6-tetradeoxy-1- O-p -nitrobenzoyl-3,4-bis(trifluoroacetamido)-β- l - lyxo -hexopyranose ( 23β ) were suitable for the glycosylation of 4- O -methyl-10- O-p -nitrobenzoyl-β-rhodomycinone by the trimethylsilyl triflate method. Saponification of the resulting 7- O -α-glycosyl-4- O -methyl-β-rhodomycinones gave 31 and 33 .