| Abstract
| - A series of individual sugar-modified pyrimidine nucleosidesincluding enantiomericallyenriched 2‘,3‘-dideoxynucleosides14a−c (α and β anomers ofl- and d-series), 2‘,3‘-dideoxy-4‘-thionucleosides 21a−c (α and βanomers of l- and d-series), and2‘,3‘-dideoxy-4‘-azanucleosides 28a−c (β anomers ofl- and d-series) were synthesized, with uniformchemistry and highstereochemical efficiency, exploiting a triad of versatile heterocyclicsiloxy dienes, namely, 2-(tert-butyldimethylsiloxy)furan (TBSOF),2-(tert-butyldimethylsiloxy)thiophene (TBSOT), andN-(tert-butoxycarbonyl)-2-(tert-butyldimethylsiloxy)pyrrole(TBSOP). The synthetic procedure advantageously used both enantiomers of glyceraldehyde acetonide(d-1 and l-1) as sourcesof chiralityand as synthetic equivalents of the formyl cation. The outlinedchemistry also allowed for therapid assemblage of a 30-member collection of racemic nucleosides(d,l-L) as well as one15-member ensemble of chiral analogues (l-L), alongwith some related sublibraries.
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