Synthetic Utility of an Isolable Nucleoside Phosphonium Salt

The reaction of O 6-benzyl-3′,5′-bis-O-(tert-butyldimethylsilyl)-2′-deoxyxanthosine with 1H-benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphate (BOP) yielded the nucleoside C-2 tris(dimethylamino)phosphonium hexafluorophosphate salt as a stable, isolable species. This is in contr...

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Bibliographic Details
Published in:Organic letters 2008-06, Vol.10 (11), p.2203-2206
Main Authors: Bae, Suyeal, Lakshman, Mahesh K
Format: Article
Language:English
Subjects:
Deoxyribonucleosides - chemistry
Organophosphorus Compounds - chemical synthesis
Organophosphorus Compounds - chemistry
Organophosphorus Compounds - isolation & purification
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Summary:The reaction of O 6-benzyl-3′,5′-bis-O-(tert-butyldimethylsilyl)-2′-deoxyxanthosine with 1H-benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphate (BOP) yielded the nucleoside C-2 tris(dimethylamino)phosphonium hexafluorophosphate salt as a stable, isolable species. This is in contrast to reactions of inosine nucleosides with BOP, where the in situ formed phosphonium salts undergo subsequent reaction to yield O 6-(benzotriazol-1-yl)inosine derivatives. The phosphonium salt obtained from the 2′-deoxyxanthosine derivative can be effectively used to synthesize N 2-modified 2′-deoxyguanosine analogues. Using this salt, a new synthesis of an acrolein-2′-deoxyguanosine adduct has also been accomplished.
ISSN:1523-7060
1523-7052
DOI:10.1021/ol8006106