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Communication | Special issue | Vol 39, No. 2, 1994, pp.491-496
Published online, 1st January, 1970
DOI: 10.3987/COM-94-S(B)74
Chiral β-Lactams as Synthons. Stereospecific Synthesis of a 6-epi-Lincosamine Derivative

Ajay K. Bose,* Chandra Mathur, Dilip R. Wagle, Raza Naqvi, Maghar S. Manhas, and Zofia Urbanczyk-Lipkowska

*Department of Chemistry and Chemical Engineering, Stevens Institute of Technology, Castle Point on the Hudson Hoboken, NJ 07030, U.S.A.

Abstract

A derivative of 6-epi-lincosamine has been prepared by a sequence of stereospecific steps from an optically active, cis-α-hydroxy-β-lactam. This β-lactam was obtained by an enantiospecific cycloaddition reaction between methoxyacetyl chloride, triethylamine and a Schiff base derived from benzylamine and an optically active aldehyde derived from D-galactopyranose.