Stereoselective Synthesis of 2-(β-C-Glycosyl)glycals: Access to Unusual β-C-Glycosides from 3-Deoxyglycals.

Autor: Reddy GM; School of Chemistry, University of Hyderabad , Hyderabad 500 046, India., Maheswara Rao BU; School of Chemistry, University of Hyderabad , Hyderabad 500 046, India., Sridhar PR; School of Chemistry, University of Hyderabad , Hyderabad 500 046, India.
Jazyk: angličtina
Zdroj: The Journal of organic chemistry [J Org Chem] 2016 Apr 01; Vol. 81 (7), pp. 2782-93. Date of Electronic Publication: 2016 Mar 14.
DOI: 10.1021/acs.joc.5b02879
Abstrakt: A novel method for the highly stereoselective synthesis of β-(1→2)-C-saccharides employing 3-deoxy- and 3-C-branched glycals as hermaphroditic substrates is revealed. The generality of the C-C bond formation reaction between the two sugar units is evaluated. The developed methodology is successfully applied to the synthesis of biologically significant subunits that are present in various natural products, which include mixed C-disaccharides with adjacent THP-THF rings, C-aryl glycosides, and highly functionalized β-C-glycosides.
Databáze: MEDLINE