Steric and Conformational Effects in the Dehalogenation of 2-Halo Sugar Derivatives with Tributylstannane

Derek Horton; Waldemar Priebe; Marcos L. Sznaidman

doi:10.1021/jo00059a037

Steric and Conformational Effects in the Dehalogenation of 2-Halo Sugar Derivatives with Tributylstannane

Derek Horton, Waldemar Priebe, Marcos L. Sznaidman

Experimental Therapeutics

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18 Scopus citations

Abstract

The stereochemistry of dehalogenation of 2-halo sugars with tributyltin hydride has been investigated in terms of the influence of steric and conformational effects using deuterium-labeling techniques. Detailed analysis of the results (Tables I–III) demonstrates that the size and orientation of the ring substituents are a determining factor in the stereochemical outcome of the reaction. However, some results can only be explained considering reduction of two equilibrating radical conformers.

Original language	English (US)
Pages (from-to)	1821-1826
Number of pages	6
Journal	Journal of Organic Chemistry
Volume	58
Issue number	7
DOIs	https://doi.org/10.1021/jo00059a037
State	Published - 1993

ASJC Scopus subject areas

Organic Chemistry

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abstract = "The stereochemistry of dehalogenation of 2-halo sugars with tributyltin hydride has been investigated in terms of the influence of steric and conformational effects using deuterium-labeling techniques. Detailed analysis of the results (Tables I–III) demonstrates that the size and orientation of the ring substituents are a determining factor in the stereochemical outcome of the reaction. However, some results can only be explained considering reduction of two equilibrating radical conformers.",

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Y1 - 1993

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AB - The stereochemistry of dehalogenation of 2-halo sugars with tributyltin hydride has been investigated in terms of the influence of steric and conformational effects using deuterium-labeling techniques. Detailed analysis of the results (Tables I–III) demonstrates that the size and orientation of the ring substituents are a determining factor in the stereochemical outcome of the reaction. However, some results can only be explained considering reduction of two equilibrating radical conformers.

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Steric and Conformational Effects in the Dehalogenation of 2-Halo Sugar Derivatives with Tributylstannane

Abstract

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