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Direct phosphorylation of nucleosides by oxyphosphorane

✍ Scribed by Xin Chen; Nan-Jing Zhang; Yan-Mei Li; Yang Jiang; Xiang Zhang; Yu-Fen Zhao

Publisher
Elsevier Science
Year
1997
Tongue
French
Weight
194 KB
Volume
38
Category
Article
ISSN
0040-4039

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✦ Synopsis

Ester exdaange reaction of oxyphosphorane 1 with tmprotected ribonudeosides cytidine 2a and adenosine 2b generated selectively spirooxyphosphoranes 3a and 3b respectively, Upon hydrolysis, the labile spirooxyphosphoranes were converted into stable ribonueleoside 2',3'-cyclic monephosphates 4a and 4b in good yields. Some polyribonudeotides were also detected from the hydrolytic products. Reaction of 1 with a 2'deoxyribonucleoside such as thymidine 5 followed by hydrolysis afforded thymidine acyelic monophosphates (7, 8). Hence, the ester exchange reaction of oxyphosphorane might provide an efficient one-pot phosphorylation methodology for ribonucleosides and 2'-dooxyribonueleosides without any protection.

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