HI/Acetic acid reduction of peracetylated N-acetyl neuraminic acid esters to stereoselectively provide α-2-deoxy-2-hydrido derivatives

Jacquelyn Gervay-Hague, Travis Q. Gregar

Research output: Contribution to journalArticle

9 Scopus citations

Abstract

Peracetylated ester derivatives of N-acetyl neuraminic acid were reacted with hydrogen iodide in acetic acid to stereoselectively provide α-2-deoxy-2-hydrido analogs, The reaction proceeds through formation of an anomeric iodide which, in the presence of excess HI, is reduced to give an enol intermediate, Kinetic protonation of the intermediate enol gives a 3.4:1 α:β mixture of 2-deoxy-2-hydrido derivatives. Under thermodynamic conditions the a-anomer is formed exclusively.

Original languageEnglish (US)
Pages (from-to)5921-5924
Number of pages4
JournalTetrahedron Letters
Volume38
Issue number34
DOIs
StatePublished - Aug 1997
Externally publishedYes

ASJC Scopus subject areas

  • Biochemistry
  • Organic Chemistry
  • Drug Discovery

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