Unprecedented lability of the 5'-O-tert-butyldimethylsilyl group from 3'-spiro-5''-(4''-acylamino-1'',2''-oxathiole-2'',2''-dioxide) nucleoside derivatives via neighboring group participation of the 4''-acylamino residue.

Abstract

Scarce examples of exceptionally mild desilylation of tert-butyldimethylsilyl (TBDMS) ether groups by neighboring group participation have been previously described. Here, we investigate, in detail, the discovery of the unusual lability of the 5'-TBDMS group on 4' '-acylamino TSAO derivatives in DMSO solution. The synthesis and comparative chemical… (More)

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