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.
Blatter
G
G
Laboratoire de Chimie des Sucres, U.R.A. 499, U.F.R. Faculté des Sciences, Université d'Orléans, France.
Beau
J M
JM
Jacquinet
J C
JC
D002236:Carbohydrate Conformation; D002240:Carbohydrate Sequence; D003847:Deoxyglucose / Q000031:analogs & derivatives*; D004187:Disaccharides / Q000138:chemical synthesis* / Q000737:chemistry; D006027:Glycosides / Q000138:chemical synthesis; D007202:Indicators and Reagents; D009682:Magnetic Resonance Spectroscopy; D008969:Molecular Sequence Data; D009844:Oligosaccharides / Q000138:chemical synthesis* / Q000737:chemistry; D009904:Optical Rotation; D013237:Stereoisomerism
D004187:Disaccharides; D006027:Glycosides; D007202:Indicators and Reagents; D009844:Oligosaccharides; D003847:Deoxyglucose