1201913-20-3Relevant academic research and scientific papers
Synthesis of difluorinated carbocyclic analogues of 5-deoxypentofuranoses and 1-amino-5-deoxypentofuranoses: en route to fluorinated carbanucleosides
Fourrière, Ga?lle,Van Hijfte, Nathalie,Lalot, Jér?me,Dutech, Guy,Fragnet, Bruno,Coadou, Ga?l,Quirion, Jean-Charles,Leclerc, Eric
experimental part, p. 3963 - 3972 (2010/07/05)
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.
Synthesis of difluorinated carbocyclic analogues of 5-deoxypentofuranoses
Fourrière, Ga?lle,Lalot, Jér?me,Hijfte, Nathalie Van,Quirion, Jean-Charles,Leclerc, Eric
scheme or table, p. 7048 - 7050 (2010/02/28)
The synthesis of difluorinated carbocyclic analogues of 5-deoxypentofuranoses is described. The sequence involves an addition of PhSeCF2TMS to carbohydrate-derived aldehydes followed by a radical cyclization, and provides a secure strategy for
