Formation of 1,1-alpha,alpha-glycosidic bonds by intramolecular aglycone delivery. A convergent synthesis of trehalose.
[reaction: see text] We report a new synthesis of trehalose analogs that involves the use of intramolecular aglycone delivery for stereoselective formation of the 1,1-alpha,alpha-glycosidic bond. The glycosylation reaction afforded the desired isomer exclusively and in good yield.
Pratt
Matthew R
MR
Center for New Directions in Organic Synthesis, Department of Chemistry, University of California, Berkeley, California 94720-1460, USA.
Leigh
Clifton D
CD
Bertozzi
Carolyn R
CR
D002240:Carbohydrate Sequence; D006027:Glycosides / Q000138:chemical synthesis*; D006031:Glycosylation; D007536:Isomerism; D008956:Models, Chemical; D008969:Molecular Sequence Data; D010084:Oxidation-Reduction; D014199:Trehalose / Q000138:chemical synthesis*
D006027:Glycosides; D014199:Trehalose