Influence of the O3 protecting group on stereoselectivity in the preparation of C-mannopyranosides with 4,6-O-benzylidene protected donors.
α-C-Glucopyranosides and mannopyranosides are obtained in 65-85% yields from 4,6-O-benzylidene-protected glucosyl and mannosyl thioglycosides bearing ester functionality at the 3-O-position by a coupling reaction with C-nucleophiles on activation with diphenyl sulfoxide, 2,4,6-tri-tert-butylpyrimidine, and trifluoromethanesulfonic anhydride.
Centre de Recherche de Gif, Institut de Chimie des Substances Naturelles, CNRS, Avenue de la Terrasse, 91198 Gif-sur-Yvette, France. dcrich@icsn.cnrs-gif.fr
David
D
Crich
Indrajeet
I
Sharma
D001597:Benzylidene Compounds / Q000737:chemistry*; D004952:Esters; D006031:Glycosylation; D007202:Indicators and Reagents / Q000737:chemistry*; D009682:Magnetic Resonance Spectroscopy; D008358:Mannose / Q000737:chemistry*; D015394:Molecular Structure; D010087:Oxides / Q000737:chemistry*; D013237:Stereoisomerism; D013865:Thioglycosides / Q000737:chemistry*
D001597:Benzylidene Compounds; D004952:Esters; D007202:Indicators and Reagents; D010087:Oxides; D013865:Thioglycosides; D008358:Mannose