Stereocontrolled synthesis of beta-2'-deoxy and 2',3'-dideoxynucleosides by intramolecular glycosylation.
Intramolecular glycosylation of phenyl 3-O-benzyl-2-deoxy-5-O-(4-methoxy-2-pyrimidyl)-1-thio-D-ribofuranoside and 2,3-dideoxy-5-O-(4-methoxy-2-pyrimidyl)-1-thio-D-glycero-pentofuranos ide by activation with dimethyl(methylthio)-sulfonium tetrafluoroborate followed by hydrolysis gave the corresponding beta-2'-deoxy and beta-2',3'-dideoxypyrimidine nucleoside derivatives respectively in good yields.
Sugimura
H
H
Noguchi Institute, Tokyo, Japan.
Sujino
K
K
Motegi
M
M
D003853:Deoxyribonucleosides / Q000138:chemical synthesis*; D015224:Dideoxynucleosides / Q000138:chemical synthesis*; D006031:Glycosylation; D006868:Hydrolysis; D011741:Pyrimidine Nucleosides / Q000138:chemical synthesis*; D013237:Stereoisomerism
D003853:Deoxyribonucleosides; D015224:Dideoxynucleosides; D011741:Pyrimidine Nucleosides