Back to results
US 9,868,755 B2Granted
Reagent-controlled stereoselective glycosylation
AssigneeTrustees of Tufts College
InventorsClay S. Bennett, John P. Issa, Dina Lloyd
Life of this patent
Estimating the term…
Abstract
Provided are methods for the efficient stereoselective formation of glycosidic bonds, without recourse to prosthetic or directing groups.
Claims25
A method of forming a glycosidic bond, comprising:
- combining a first solvent, a reducing sugar, and a first strong Bronsted base, thereby forming a first reaction mixture;
- combining a sulfonylating agent and the first reaction mixture, thereby forming a glycosyl sulfonate;
- combining a second solvent, a glycosyl acceptor, and a second strong Bronsted base, thereby forming a second reaction mixture;
- and
- combining the glycosyl sulfonate and the second reaction mixture, thereby forming a glycosidic bond;
- wherein the reducing sugar is a pyranose;
- the sulfonylating agent is a sulfonyl halide;
- and
- the glycosidic bond is formed with greater than or equal to 90% stereoselectivity for a β linkage.
6 more elements
Dependencies are inferred from the claim text.