Synthesis of 2'-deoxy and 2',3'-dideoxynucleoside derivatives from thioglycosides.
The synthesis of both 2'-deoxy and 2',3'-dideoxynucleoside derivatives by the reaction of thioglycosides with nucleoside bases was examined. The stereochemical outcome at the anomeric position was found to depend on the protecting groups and the C-3 configuration in the sugar moiety, the kind of activator, and the reaction temperature. Based on these findings, 2'-deoxy-D-xylo nucleoside and 2',3'-dideoxynucleoside derivatives have been synthesized in beta-selective manner.
Sugimura
H
H
Noguchi Institute, Tokyo, Japan.
Sujino
K
K
Osumi
K
K
D003853:Deoxyribonucleosides / Q000138:chemical synthesis*; D015224:Dideoxynucleosides / Q000138:chemical synthesis*; D015394:Molecular Structure; D013237:Stereoisomerism; D013865:Thioglycosides / Q000737:chemistry*
D003853:Deoxyribonucleosides; D015224:Dideoxynucleosides; D013865:Thioglycosides