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

Maria   Chiara   Aversa; Anna      Barattucci; Paola      Bonaccorsi; Giuseppe      Bruno; Placido      Giannetto; Patrick      Rollin

doi:10.2174/1570178043400631

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.

Keywords: anomeric effect, stereoselective oxidation, 1-thioglycosides

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Letters in Organic Chemistry

Title: 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

Volume: 1 Issue: 4

Author(s): Maria Chiara Aversa, Anna Barattucci, Paola Bonaccorsi, Giuseppe Bruno, Placido Giannetto and Patrick Rollin

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Keywords: anomeric effect, stereoselective oxidation, 1-thioglycosides

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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Aversa Chiara Maria, Barattucci Anna, Bonaccorsi Paola, Bruno Giuseppe, Giannetto Placido and Rollin Patrick, 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, Letters in Organic Chemistry 2004; 1 (4) . https://dx.doi.org/10.2174/1570178043400631