The use of 2-deoxy-2-trichloroacetamido-d-glucopyranose derivatives in syntheses of oligosaccharides

3,4,6-Tri-O-acetyl-2-deoxy-2-trichloroacetamido-alpha-D-glucopyran osyl trichloroacetimidate and its O-benzylated analogue were tested as glycosyl donors in the reaction with a set of sugar acceptors unsubstituted on O-3 and O-4, typically encountered in the synthesis of oligosaccharides. Glycosides were obtained in good to excellent yields with only a slight excess (1.1-1.2 equiv) of the donor, and with a high degree of 1,2-trans stereoselectivity. The corresponding 2-(trichloromethyl)oxazolinium ion was postulated to be the major reactive intermediate. The N-trichloroacetyl groups in the disaccharide products were easily transformed into N-acetyl under neutral conditions by reduction with tributylstannane.