Stereoselective Synthesis Of Ribonucleoside 3’,5’-Cyclic Methyl(Phenyl)Phosphonates And Phosphonothioates

H. C.P.F. Roelen, E. D. Vroom, G. A.V. Der Marel, J. H.van Boom, A. H.J. Wang

Research output: Contribution to journalArticlepeer-review

4 Citations (Scopus)


Monophosphonylation of 2’-protected ribonucleosides (i.e., 2’-O-THP-uridine and 2’-O-THP-N6-levulinoyl-adenosine) with the bifunctional reagents bis[( 6-trifluoromethyl)benzotriazol-1-yl] methyl(phenyl)phosphonates or the analogous phosphonothioates, and subsequent addition of N-methylimidazole gave the chirally pure ‘,5’methyl(phenyl)phosphonate or phosphonothioate derivatives, respectively. Deblocking of the fully protected compounds yielded, as evidenced by X-ray analysis. the corresponding pure Sp-diastereoisomers.

Original languageEnglish
Pages (from-to)141-156
Number of pages16
JournalNucleosides and Nucleotides
Issue number1
Publication statusPublished - Jan 1 1992
Externally publishedYes

ASJC Scopus subject areas

  • Biochemistry
  • Genetics


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