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

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

Affiliation:

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.

Cite this article as:

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