3-EPISTREPTOMYCIN OR ITS DIHYDRO-DERIVATIVE

摘要

NEW MATERIAL:The compound of formulaI(R is -CH2OH or -CHO) or its salt. EXAMPLE:3''-Epidihydrostreptomycin carbonate. USE:An antibacterial agent effective to resistant Gram-negative bacteria. PROCESS:The compound of formulaIcan be prepared e.g. by (1) protecting the 2''- methylamino group of the dihydrostreptomycin of formula II with benzyloxycarbonyl group, (2) protecting the hydroxyl groups at the 3'-, 3'a-, 4''- and 6''- positions with acetyl groups, etc., (3) protecting all the other hydroxyl groups and all guanidyl groups, (4) eliminating the 2''-N-benzyloxycarbonyl group and then 3''-acetyl group, (5) protecting the 2''-methylamino group again, (6) trifluoromethylsulfonylating the 3''-position of the product, (7) condensing and cyclizing with the 2''-position, (8) introducing carbamate group, and (9) eliminating all protecting groups from the product.