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- ISSN: 1570-1786
- E-ISSN: 1875-6255
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The Role of the exo-Anomeric Effect in the Stereoselective Oxidation of 1- Thioglycosides: A Contribution in the α-D-Glucopyranoside Series Using XRay Crystallography
- Source: Letters in Organic Chemistry, Volume 1, Issue 4, Oct 2004, p. 376 - 380
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- 01 Oct 2004
Abstract
X-Ray crystallographic analysis of an enantiopure 1-thio-α-D-glucopyranoside S-oxide clearly supports the role of the exo-anomeric effect in determining the highly stereoselective oxidation of α- thioglycosides to (RS) sulfoxides. Ab-initio and DFT calculations point out the relevance of the anomeric effect, due to the presence of sulfur at position 1, in determining some structural characteristics of aldohexosyl sulfoxides.
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