title: Reaction of 1,2-orthoesters with HF-pyridine: a method for the preparation of partly unprotected glycosyl fluorides and their use in saccharide synthesis.
abstract: 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.
authors.affiliation: Instituto de Química Orgánica General (CSIC), Juan de la Cierva 3, 28006 Madrid, Spain. clopez@iqog.csic.es
authors.forename: J Cristóbal
authors.initials: JC
authors.lastname: López
authors.forename: Juan
authors.initials: J
authors.lastname: Ventura
authors.forename: Clara
authors.initials: C
authors.lastname: Uriel
authors.forename: Ana M
authors.initials: AM
authors.lastname: Gómez
authors.forename: Bert
authors.initials: B
authors.lastname: Fraser-Reid
mesh_terms: D002241:Carbohydrates / Q000138:chemical synthesis* / Q000737:chemistry; D005459:Fluorides / Q000138:chemical synthesis* / Q000737:chemistry; D006858:Hydrofluoric Acid / Q000737:chemistry*; D015394:Molecular Structure; D011725:Pyridines / Q000737:chemistry*; D013329:Structure-Activity Relationship
chemical_list: D002241:Carbohydrates; D011725:Pyridines; D005459:Fluorides; D006858:Hydrofluoric Acid