Convenient and Efficient Approach to Di- and Trideoxyribonucleotide N3’-P5’ Phosphoramidates

Arbuzov reaction of phenyl phosphorodichloridite with an equivalent of allyl alcohol and tert-butyl alcohol produced phenyl allyl Hphosphonate and the subsequent ester-exchange with various nucleosides produced nucleoside allyl H-phosphonates. AnthertonTodd reaction of the nucleoside allyl H-phosphonates with 3’-amino-3’-deoxythymidine yielded dideoxyribonucleotide N3’-P5’ phosphoramidates, and the repetition of this procedure provided trideoxyribonucleotide N3’-P5’ phosphoramidates. The method can be used for the synthesis of oligodeoxyribonucleotide N3’-P5’ phosphoramidates without any protection for all nucleosides.