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Synthetic Utility of an Isolable Nucleoside Phosphonium Salt.

  作者 Bae, Suyeal;Lakshman, Mahesh K.;  
  选自 期刊  Organic Letters;  卷期  2008年10-11;  页码  2203-2206  
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[摘要]The reaction of O6-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 O6-(benzotriazol-1-yl)inosine derivs. The phosphonium salt obtained from the 2'-deoxyxanthosine deriv. can be effectively used to synthesize N2-modified 2'-deoxyguanosine analogs. Using this salt, a new synthesis of an acrolein-2'-deoxyguanosine adduct has also been accomplished.

 
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