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

doi:10.1016/S0040-4039(97)01323-3

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 journal › Article

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 language	English (US)
Pages (from-to)	5921-5924
Number of pages	4
Journal	Tetrahedron Letters
Volume	38
Issue number	34
DOIs	https://doi.org/10.1016/S0040-4039(97)01323-3
State	Published - Aug 1997
Externally published	Yes

ASJC Scopus subject areas

Biochemistry
Organic Chemistry
Drug Discovery

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Gervay-Hague, J., & Gregar, T. Q. (1997). HI/Acetic acid reduction of peracetylated N-acetyl neuraminic acid esters to stereoselectively provide α-2-deoxy-2-hydrido derivatives. Tetrahedron Letters, 38(34), 5921-5924. https://doi.org/10.1016/S0040-4039(97)01323-3

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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.",

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AU - Gregar, Travis Q.

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AB - 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.

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