Stereoselective glycosylation reactions

摘要

Disclosed is a method for selective synthesis of 1,2-cis-α-linked glycosides which does not require the use of the specialized protecting group patterns normally employed to control diastereoselectivity. Thioglycoside acceptors can be used, permitting iterative oligosaccharide synthesis. The approach eliminates the need for lengthy syntheses of monosaccharides possessing highly specialized and unconventional protecting group patterns.

主权项

1. A method of forming a glycosidic bond, comprising:
combining a glycosyl phenyl sulfide, phenyl sulfoxide, molecular sieves, and a non-nucleophilic base, thereby forming a first reaction mixture; combining trifluoromethanesulfonic anhydride and the first reaction mixture, thereby forming a second reaction mixture; combining tetrabutylammonium iodide (TBAI) and the second reaction mixture, thereby forming a third reaction mixture; and combining a glycosyl acceptor and the third reaction mixture, thereby forming a glycosidic bond; wherein the glycosidic bond is formed with greater than or equal to 90% stereoselectivity for an α linkage.