Synthesis of 3’-Phosphates of Diribonucleoside Monophosphates Via Phosphotriester Intermediates

J. H. van Boom, P. M.J. Burgers, C. A.G. Haasnoot

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Phosphorylation of the easily accessible 3’, 5’-diesters 1a-d with diphenyl phosphorochloridate, followed by selective 5’-deacylation, affords the phosphotriester derivatives 2a-d in good yields. Alkaline treatment of 2a-d results in the formation of the 2’, 3’-cyclic phosphates (3a-d). The usefulness of the phosphotriester derivatives 2a-d is also demonstrated in the synthesis of the nucleotidyl-(3’-5’) nucleoside 3’-phosphates U-Up18 (10a), U-Ap (11a). U-Cp (12a) and A-Gp (13a). The fully protected dinucleoside diphosphates 5c-8c, prepared by the phosphotriester method, are deprotected in two ways: (a) by a purely chemical method, affording the dinucleoside diphosphates in a circa one to one mixture of 2’- and 3’- isomers, 10b-13b and 10a-13a, respectively, and (b) by a mixed chemical-enzytnatical approach which gives the pure 3’-phosphates (10a-13a).

Original languageEnglish
Pages (from-to)2731-2748
Number of pages18
JournalNucleic acids research
Issue number10
StatePublished - Oct 1976
Externally publishedYes

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