A synthesis of dihydrostreptomycin.

A key protected streptidine derivative (3) useful for the synthesis of antibiotics of streptomycin series was prepared by hydrolysis of an acylated dihydrostreptomycin (DHSM) derivative (2), and it was condensed with a protected dihydrostreptobiosaminyl chloride (5) to give two condensation products (6 and 7). By deblocking, 6 was led to DHSM and 7 to a biologically inactive isomer (8) of DHSM. From the PMR spectrum of 4-O-mesyl derivative (4) of 3, the benzyloxycarbonyl and acetyl groups were concluded to be attached to the end nitrogens of the guanidine groups.