2010
DOI: 10.1002/ejoc.200900950
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Preparation of Carbocyclic C‐Nucleosides from α‐Chlorooxime Precursor

Abstract: The syntheses of L‐carbocyclic benzothiazolo, benzoxazolo, and benzimidazolo C‐nor‐nucleosides are described. The key step is the reaction of the C‐chlorooxime 7, obtained by C‐chlorination with N‐chlorosuccinimide of [(1S,2R,3R,4R)‐1‐tert‐butyldimethylsiloxy‐2,3‐(O‐isopropylidenedioxy)]cyclopentane‐4‐carbohydroximic acid (6), with different α‐amino aromatic compounds. Acidic deprotection gave the benzoxazolo (11), benzimidazolo (12), and benzothiazolo (13) title compounds, in good yields.

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