Patent ID: 6960654

Claim:
A method of forming a glycosidic bond comprising: (a) providing a thioglycoside having a thio moiety, SR, wherein R is aryl or alkyl; (b) activating the thioglycoside by treatment with (i) trifluoromethanesulfonic anhydride, (ii) a N,N-dialkylsulfinamide having a structure wherein R 1 is selected from the group consisting of aryl, heteroaryl, and C 1-6 alkyl; and R 2 and R 3 , independently, are C 1-6 alkyl, or R 2 and R 3 are taken together with the nitrogen atom to which they are attached to form a 4- to 8-membered aliphatic ring, optionally containing an additional nitrogen atom, an oxygen atom, or a sulfur atom; and (iii) an optional sterically hindered base; (c) adding an alcohol or an amine to the activated thioglycoside to substitute an alcohol residue or an amine residue for the thio moiety of the thioglycoside by formation of the glycosidic bond.