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Synthesis 1993; 1993(4): 421-425
DOI: 10.1055/s-1993-25875
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Syntheses of (2S,3S)-[4,4,4-2H3]- and (2S,3R)-[4,4,4-2H3]Penicillamine

Palaniappagownder Nanjappan* , Kondareddiar Ramalingam, Henry I. Mosberg, Ronald W. Woodard
  • *Department of Medicinal Chemistry, College of Pharmacy, The University of Michigan, Ann Arbor, Michigan 48 109-1065, USA
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Publication Date:
17 September 2002 (online)

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(2S,3S)-[4,4,4-2H3]- and (2S,3R)-[4,4,4-2H3]Penicillamine (2-amino-3-mercapto-3-methyl-[4,4,4-2H3]butanoic acids) were synthesized from benzyl (1S,3S,6R)-6-(phenoxyacetylamino)penicillanate 1-oxide and allyl (1R,3S,6R)-6-phthalimidopenicillanate 1-oxide, respectively. The two key steps are the stereospecific sulfur oxidation of the 6-phenoxyacetylamino- versus the 6-phthalimidopenicillanic acid to provide the (1S) and (1R) sulfoxides, respectively, and the exclusive exchange of the hydrogen atoms of the C-2 methyl that are cis to oxygen of the sulfoxide group with the deuterium of deuterium oxide.