1201555-80-7Relevant academic research and scientific papers
Application of germyldesulfonylation reactions to the synthesis of germanium-containing nucleoside analogues
Wnuk, Stanislaw F.,Sacasa, Pablo R.,Restrepo, Jorge
, p. 537 - 549 (2009)
Treatment of the protected (E)-5'-deoxy-5'-[(p-toluenesulfonyl)methylene] uridine and adenosine derivatives with tributyl- or triphenylgermane hydride (AIBN/toluene/) effected radical-mediated germyldesulfonylations to give 5'-(tributyl- or triphenylgermyl)methylene-5'-deoxyuridine and adenosine derivatives as single (E)-isomers. Analogous treatment of 2'-deoxy-2'- [(phenylsulfonyl)methylene]uridine with Ph3GeH afforded the corresponding vinyl triphenylgermane product. Stereoselective halodegermylation of the (E)-5'-(tributylgermyl)methylene-5'-deoxy nucleosides with N-iodosuccinimide or N-bromosuccinimide provided the Wittig-type (E)-5'-deoxy-5'-(halomethylene) nucleosides quantitatively, while no halodegermylations was observed with the 5'-deoxy-5'-(triphenylgermyl)methylene counterparts. Treatment of the vinyl trialkylgermanes with aqueous trifluoroacetic acid effected protiodegermylation, while vinyl triarylgermanes were stable under the acidic conditions.
