3-DEOXYSTREPTOMYCIN

摘要

NEW MATERIAL:3''-Deoxystreptomycin of formulaIand a salt thereof. USE:An antibiotic substance effective for germs resistant to the streptomycin. PROCESS:A protecting group is introduced into 3''-deoxydihydrostreptomycin of formula II, and the methylol group at the 3'-position is oxidized and converted into an aldehyde. The protecting group is then eliminated to prepare the compound of formulaI. For introducing the protecting group, the methylamino group at the 2''-position is selectively protected by a protecting group of the amino group, and two OH groups at the 3'- and 3'a-positions are protected. All the OH groups of the resultant compound are then protected. The OH groups at the 3'- and 3'a-positions are then liberated from the protecting groups to oxidize the methylol groups. The reaction is preferably carried out by using dicyclohexylcarbodiimide in the presence of pyridine or trifluoroacetic acid in anhydrous dimethyl sulfoxide (DMSO). The acetyl groups and the protecting group of the amino group at the 2''-position of the resultant compound are then eliminated to prepare the compound of formulaI.