Reaction of 1,2-orthoesters with HF-pyridine: a method for the preparation of partly unprotected glycosyl fluorides and their use in saccharide synthesis.

J Cristóbal López, Juan Ventura, Clara Uriel, Ana M Gómez, Bert Fraser-Reid

Instituto de Química Orgánica General (CSIC), Juan de la Cierva 3, 28006 Madrid, Spain. clopez@iqog.csic.es

Organic letters 2009 Sep 17

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Glycosyl fluorides can be prepared in an efficient manner by treatment of pyranose- or furanose-derived 1,2-orthoesters, with hydrogen fluoride pyridine (HF-py). The method is compatible with the presence of a variety of protecting groups, including tert-butyldiphenyl silyl ethers, and can be applied to sugar derivatives with free hydroxyl groups, thus avoiding the need for the protection-deprotection steps.

Citation

J Cristóbal López, Juan Ventura, Clara Uriel, Ana M Gómez, Bert Fraser-Reid. Reaction of 1,2-orthoesters with HF-pyridine: a method for the preparation of partly unprotected glycosyl fluorides and their use in saccharide synthesis. Organic letters. 2009 Sep 17;11(18):4128-31