SYNTHETIC STUDIES ON BETA-LACTAM ANTIBIOTICS .10. SYNTHESIS OF 7-BETA-[2-CARBOXY-2-(4-HYDROXYPHENYL)ACETAMIDO]-7-ALPHA-METHOXY-3-[[(1-METHYL-1H-TETRAZOL-5-YL)THIO]-METHYL]-1-OXA-1-DETHIA-3-CEPHEM-4-CARBOXYLIC ACID DISODIUM SALT (6059-S) AND ITS RELATED 1-OXACEPHEMSH

Recently, syntheses and antibacterial activity3-5 of 1-oxacephems have increasingly attracted notice. Christensen and his co-workers have published the synthesis of dM-oxacephalothin (dM)4a and dM-oxacefamandole (dl-2),4b and the available data suggested that the former was somewhat less potent than cephalothin but the latter compound was approximately twice as superior to cefamandole with respect to antibacterial activity. In a preceding communication6 from our laboratories, the synthesis of several optically active 3-methyl-l-oxacephems 3 was reported, as well as the finding of a four-to eightfold superiority of these compounds in activity as compared with their 1-thia congeners. These findings stimulated subsequent studies on the synthesis and antibacterial activity of optically active 3-substituted methyl-l-oxacephems and 7a-methoxy compounds, including 1-oxacephalothin (1), 1-oxacefamandole (2), 7α-methoxy-1. © 1979, American Chemical Society. All rights reserved.