Influence of protecting groups on the reactivity and selectivity of glycosylation: chemistry of the 4,6-o-benzylidene protected mannopyranosyl donors and related species.
The genesis and development of the 4,6-O-benzylidene acetal method for the preparation of β-mannopyranosides are reviewed. Particular emphasis is placed on the influence of the various protecting groups on stereoselectivity and these effects are interpreted in the framework of a general mechanistic scheme invoking a series of solvent-separated and contact ion pairs in dynamic equilibrium with a covalent α-glycosyl trifluoromethanesulfonate.
Centre de Recherche de Gif, Institut de Chimie des Substances Naturelles, CNRS, 1 avenue de la Terrasse, 91198, Gif-sur-Yvette, France.
Sylvain
S
Aubry
Kaname
K
Sasaki
Indrajeet
I
Sharma
David
D
Crich
D001597:Benzylidene Compounds / Q000737:chemistry*; D004583:Electrons; D006031:Glycosylation; D008358:Mannose / Q000737:chemistry*; D012451:Safrole / Q000031:analogs & derivatives / Q000737:chemistry; D013237:Stereoisomerism; D013865:Thioglycosides / Q000737:chemistry
D001597:Benzylidene Compounds; D013865:Thioglycosides; D008358:Mannose; D012451:Safrole; C005746:sulfoxide