Synthesis of difluorinated carbocyclic analogues of 5-deoxypentofuranoses and 1-amino-5-deoxypentofuranoses: en route to fluorinated carbanucleosides

• DOI: 10.1016/j.tet.2010.03.079
• Publication Date: 2010-03-30T17:28:00Z
• Authors: Gaëlle Fourrière; Nathalie Van Hijfte; Jérôme Lalot; Guy Dutech; Bruno Fragnet; Gaël Coadou; Jean-Charles Quirion; Eric Leclerc
• Keywords: Sequence (biology)

The synthesis of difluorinated carbocyclic analogues of 5-deoxypentofuranoses and 1-amino-5-deoxypentofuranoses is described. The sequence involves an addition of PhSeCF2TMS to carbohydrate-derived aldehydes or their corresponding tert-butanesulfinylimines followed by a radical cyclization. Optimized conditions for the PhSeCF2TMS addition to α-chiral aldehydes have been disclosed and its unusual diastereoselectivity is discussed. Application of the sequence using Ellman's auxiliary allows a more direct access to 1-aminopentose analogues with a complete control of the pseudo-anomeric center configuration.