Synthesis of difluorinated carbocyclic analogues of 5-deoxypentofuranoses and 1-amino-5-deoxypentofuranoses: en route to fluorinated carbanucleosides |
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Authors: | Gaëlle Fourrière |
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Institution: | Université et INSA de Rouen, CNRS, UMR 6014 C.O.B.R.A.-IRCOF, 1 rue Tesnière, 76821 Mont Saint-Aignan Cedex, France |
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Abstract: | 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. |
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Keywords: | Nucleosides Carbasugars Fluorine Radical cyclization |
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