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

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 interme...

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Bibliographic Details
Published inTetrahedron letters Vol. 38; no. 34; pp. 5921 - 5924
Main Authors Gervay, Jacquelyn, Gregar, Travis Q.
Format Journal Article
LanguageEnglish
Published OXFORD Elsevier Ltd 01.08.1997
Elsevier
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
SIALIDASE
ACETYLNEURAMINIC ACID
ANALOGS
BEHAVIOR
VIBRIO-CHOLERAE
STRUCTURAL VARIATIONS
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Summary: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 α-anomer is formed exclusively. The anomeric acetate was quantitatively converted to the iodide and subsequently reduced to give the thermodynamic product.
ISSN:0040-4039
1873-3581
DOI:10.1016/S0040-4039(97)01323-3