Synthesis of 3'alpha-carbo-substituted 2',3'-dideoxyribonucleosides from naturally occurring nucleosides.
Naturally occurring ribonucleosides, uridine and adenosine, were converted to their 3'alpha-CH2CO2Me and 3'alpha-CH2PO(OPh)2 2',3'-dideoxy analogues. The present reaction sequence starts with oxidative cleavage of the 2',3'-cis-diol system, and involves radical-mediated reconstruction of furanose ring as the key step.
Kumamoto
H
H
School of Pharmaceutical Sciences, Showa University, Tokyo, Japan.
Tanaka
H
H
Ogamino
J
J
Suzuki
H
H
Haraguchi
K
K
Miyasaka
T
T
D000241:Adenosine; D015224:Dideoxynucleosides / Q000138:chemical synthesis* / Q000737:chemistry; D015195:Drug Design; D007202:Indicators and Reagents; D008968:Molecular Conformation; D014529:Uridine
D015224:Dideoxynucleosides; D007202:Indicators and Reagents; D000241:Adenosine; D014529:Uridine