Application of Germyldesulfonylation Reactions to the Synthesis of Germanium-Containing Nucleoside Analogues

Autor:	Pablo R. Sacasa, Jorge Restrepo, Stanislaw F. Wnuk
Rok vydání:	2009
Předmět:	Aqueous solution Germanium Hydride Nucleosides General Medicine Biochemistry Medicinal chemistry Toluene Article Uridine chemistry.chemical_compound chemistry Genetics Trifluoroacetic acid Molecular Medicine Organic chemistry Stereoselectivity Sulfones Methylene Nucleoside
Zdroj:	Nucleosides, Nucleotides & Nucleic Acids. 28:537-549
ISSN:	1532-2335 1525-7770
DOI:	10.1080/15257770903054340
Popis:	Treatment of the protected (E)-5'-deoxy-5'-[(p-toluenesulfonyl)methylene]uridine and adenosine derivatives with tributyl- or triphenylgermane hydride (AIBN/toluene/Delta) 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 Ph(3)GeH 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.
Databáze:	OpenAIRE
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