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First stereoselective synthesis of an optically pure β-substituted histidine: (2S,3S)-β-methylhistidine

Authors
Journal
Tetrahedron Letters
0040-4039
Publisher
Elsevier
Publication Date
Volume
41
Issue
9
Identifiers
DOI: 10.1016/s0040-4039(99)02223-6
Keywords
  • Asymmetric Synthesis
  • Chiral Auxiliary
  • β-Substituted Histidine
  • Amino Acids
  • Mesitylenesulfonyl

Abstract

Abstract We report the first example of the asymmetric synthesis of the β-substituted histidine, (2 S,3 S)-β-methylhistidine. A key in the synthesis is the use of the protecting group, 2-mesitylenesulfonyl (Mts-), for the imidazole ring to minimize epimerization during synthesis.

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