Abstract: What are disclosed are compounds, useful as intermediates in the preparation of substituted penem compounds, of the formula ##STR1## methods for making such compounds from intermediates of the formula ##STR2## by reaction of the latter with a nucleophilic compound, methods for making such intermediates from compounds of the formula ##STR3## by reaction of the last-mentioned compounds with a tervalent phosphorus compound, and methods for making said last-mentioned compounds by cyclizing compounds of the formula ##STR4## with a tervalent phosphorus compound.

Abstract: A series of novel 7-(D-.alpha.-acylaminoarylacetamido)-.DELTA..sup.3 -cephem derivatives have been prepared wherein the acyl moiety contains an epoxy group immediately adjacent to the carbonyl carbon atom. These compounds are useful as antibacterial agents for the treatment of diseases caused by Gram-negative and Gram-positive bacteria. Preferred members include 7-[D-.alpha.-(cis-2-carboxyoxiran-3-carboxamido)phenylacetamido]-3-(1-meth yl-1,2,3,4-tetrazol-5-ylthiomethyl)-.DELTA..sup.3 -cephem-4-carboxylic acid and 7-[D-.alpha.-(cis-2-carboxyoxiran-3-carboxamido)phenylacetamido]cephalospo ranic acid. Alternate methods of preparation are provided for these compounds and the principal synthetic route is described in detail.

Abstract: A series of novel 7-(D-.alpha.-acylaminoarylacetamido)-.DELTA..sup.3 -cephem derivatives have been prepared wherein the acyl moiety contains an epoxy group immediately adjacent to the carbonyl carbon atom. These compounds are useful as antibacterial agents for the treatment of diseases caused by Gram-negative and Gram-positive bacteria. Preferred members include 7-[D-.alpha.-(cis-2-carboxyoxiran-3-carboxamido)phenylacetamido]-3-(1-meth yl-1,2,3,4-tetrazol-5-ylthiomethyl)-.alpha..sup.3 -cephem-4-carboxylic acid and 7-[D-.alpha.-(cis-2-carboxyoxiran-3-carboxamido)phenylacetamido]cephalospo ranic acid. Alternate methods of preparation are provided for these compounds and the principal synthetic route is described in detail.

Abstract: 1-N-(.omega.-Amino-2-hydroxyalkyl) derivatives of aminoglycoside antibiotics are prepared by reductive alkylation of the parent antibiotic, or a partially protected derivative thereof, with a 6-dihydroxymethyltetrahydro-1, 3-oxazin-2-one or 5-dihydroxymethyloxazolidin-2-one, followed by hydrolysis, and, if necessary, followed by removal of any remaining protecting groups. The products of the process of this invention are known antibacterial agents.