The synthesis and antiviral evaluation of 2',3'-dideoxy and 2',3'-didehydro-2',3'-dideoxy 4'thionucleosides in both enantiomeric series are described. Enantiomeric 4-O-silylated-4hydroxymethyl-4-thiobutyrolactones, produced in high yield from chiral glycidols, provided suitable chiral synthons: phen
✦ LIBER ✦
ChemInform Abstract: Synthesis and Antiviral Evaluation of Enantiomeric 2′,3′-Dideoxy- and 2′,3′-Didehydro-2′,3′-dideoxy-4′-thionucleosides.
✍ Scribed by R. J. YOUNG; S. SHAW-PONTER; J. B. THOMSON; J. A. MILLER; J. G. CUMMING; A. W. PUGH; P. RIDER
- Book ID
- 112029401
- Publisher
- John Wiley and Sons
- Year
- 2010
- Weight
- 34 KB
- Volume
- 27
- Category
- Article
- ISSN
- 0931-7597
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We have identified a selective S(N)2' reaction triggered by iodide ion that leads to the ring-opening of 2,2'-anhydro-α-nucleosides. By applying the method, we have synthesized α-D-2',3'-didehydro-2',3'-dideoxy-3'-C-hydroxymethyl nucleosides, designed as potential antiviral agents.