Preparation of 56-O-alkyl derivatives of aglycones and pseudoaglycones of teicoplanin as antibacterials

Title compds. [I; A = (cyclo)alkyl, cyanoalkyl, cycloalkylalkyl, (substituted) phenylalkyl, (unsatd.) lactone moiety, acylalkyl, carbamoylalkyl, etc.; A1 = H, Cl; R, R1 = H, (cyclo)alkyl, cyanoalkyl, alkylcarbonyloxyalkyl, (substituted) phenylalkyl, etc.; Y = OH, haloalkoxy, hydroxyalkoxy, alkyl, (substituted) phenylalkyl, acylalkyl, carbamoylalkyl, amino; B = H, N-acetyl-β-D-2-deoxy-2-aminoglucopyranosyl; M = H, α-D-mannopyranosyl], were prepd. as antibacterials. Thus, PhCH2O2CCl in acetone was added to a soln. of antibiotic L 17392 and Et3N in DMF and the mixt. was stirred 2 h to give ∼94% N15-carbobenzyloxydeglucoteicoplanin. The latter was converted to the Me ester with MeI/KHCO3 in DMF. The ester was alkylated with 1-bromo-2,3-epoxypropane/K2CO3 in ME2SO and the product was hydrogenated over Pd/BaSO4 to give I (R, R1 = H, A = 2,3-epoxypropyl, A1 = Cl, B, M = H, Y = MeO). The latter had min. inhibitory concns. of 0.125, 1, and 0.063 μM against Staphylococcus aureus Tour L165, S. haemolyticus L602, and S. epidermis ATCC 12228, resp.