Organic Letters 2003-05-01

Ph2SO/Tf2O: a powerful promotor system in chemoselective glycosylations using thioglycosides.

Jeroen D C Codée, Remy E J N Litjens, René den Heeten, Herman S Overkleeft, Jacques H van Boom, Gijs A van der Marel

Index: Org. Lett. 5(9) , 1519-22, (2003)

Full Text: HTML

Abstract

Diphenylsulfoxide in combination with triflic anhydride provides a very potent thiophilic glycosylation promotor system, capable of activating disarmed thioglycosides. The usefulness of this novel thiophilic activator is illustrated in a successful chemoselective glycosylation sequence in which the donor thioglycoside in the first condensation step may be either armed or disarmed. [reaction: see text]