Radical-based transformation of vicinal diols to olefins via thioxocarbamate derivatives: a simple approach to 2′,3′-didehydro-2′,3′-dideoxynucleosides

The bis- O-thioxocarbamate derivatives obtained from the reaction of vicinal diols with phenyl isothiocyanate are shown to be reduced with tris(trimethylsilyl)silane in the presence of azobisisobutyronitrile to afford the corresponding olefins in good yields. In this way, 2′,3′-didehydro-2′,3′-dideo...

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Bibliographic Details
Published inTetrahedron letters Vol. 44; no. 21; pp. 4027 - 4029
Main Authors Oba, Makoto, Suyama, Mitsuteru, Shimamura, Atsushi, Nishiyama, Kozaburo
Format Journal Article
LanguageEnglish
Published OXFORD Elsevier Ltd 19.05.2003
Elsevier
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
SECONDARY ALCOHOLS
ALIPHATIC-ALCOHOLS
REDUCTION
DITHIOCARBONATES
DEOXYGENATION
NUCLEOSIDES
INVENTION
2',3'-DIDEOXYNUCLEOSIDES
ATOM
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Summary:The bis- O-thioxocarbamate derivatives obtained from the reaction of vicinal diols with phenyl isothiocyanate are shown to be reduced with tris(trimethylsilyl)silane in the presence of azobisisobutyronitrile to afford the corresponding olefins in good yields. In this way, 2′,3′-didehydro-2′,3′-dideoxy analogs of adenosine, guanosine, inosine, cytidine and uridine were prepared by the radical-based deoxygenation of the corresponding ribonucleosides via the bis- O-thioxocarbamate derivatives. Graphic
ISSN:0040-4039
1873-3581
DOI:10.1016/S0040-4039(03)00847-5