Stereoselective synthesis and conformational study of novel 2′,3′-didehydro-2′,3′-dideoxy-4′-selenonucleosides

Dilip K. Tosh, Jun Choi Won, Ok Kim Hea, Yoonji Lee, Shantanu Pal, Xiyan Hou, Jungwon Choi, Sun Choi, Shin Jeong Lak

Research output: Contribution to journalArticle

17 Scopus citations

Abstract

(Chemical Equation Presented) Stereoselective synthesis of novel 2′,3′-didehydro-2′,3′-dideoxy-4′- selenonucleosides (4′-seleno-d4Ns) 4a-c was accomplished via 4′-selenoribofuranosyl pyrimidines 11a-c, as key intermediates. 4′-Selenoribofuranosyl pyrimidines 11a-c were efficiently synthesized from D-ribose or D-gulonic γ-lactone using a Pummerer-type condensation as a key step. Introduction of 2′,3′-double bond was achieved by treating cyclic 2′,3′-thiocarbonate with 1,3-dimethyl-2-phenyl-1,3,2- diazaphospholidine.

Original languageEnglish (US)
Pages (from-to)4259-4262
Number of pages4
JournalJournal of Organic Chemistry
Volume73
Issue number11
DOIs
StatePublished - Jun 6 2008
Externally publishedYes

ASJC Scopus subject areas

  • Organic Chemistry

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    Tosh, D. K., Won, J. C., Hea, O. K., Lee, Y., Pal, S., Hou, X., Choi, J., Choi, S., & Lak, S. J. (2008). Stereoselective synthesis and conformational study of novel 2′,3′-didehydro-2′,3′-dideoxy-4′-selenonucleosides. Journal of Organic Chemistry, 73(11), 4259-4262. https://doi.org/10.1021/jo8003277