Synthesis of (1′ R, 3S, 4S)??3??[1′??(tert??Butyldimethylsilyloxy) ethyl]??4??(cyclopropylcarbonyloxy) azetidin??2??one

…, M Cérésiat, J Marchand??Brynaert

Index: Laurent, Mathieu; Ceresiat, Marcel; Marchand-Brynaert, Jacqueline European Journal of Organic Chemistry, 2006 , # 16 p. 3755 - 3766

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Citation Number: 15

Abstract

Abstract The novel carbapenem precursor 1e has been synthesized from L-threonine, cyclopropyl methyl ketone and benzhydrylamine (for the introduction of the azetidinone N- protecting group). Two independently prepared building blocks–sodium (2R, 3R)-2, 3- epoxybutyrate as a mixed salt with NaBr (2b) and N-(benzhydryl) aminomethyl cyclopropyl ketone (4e)–were coupled to give (2R, 3R)-N-(benzhydryl)-N-(2-cyclopropyl-2-oxoethyl)-2 ...