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