Reaction of 1,2-orthoesters with HF-pyridine: a method for the preparation of partly unprotected glycosyl fluorides and their use in saccharide synthesis.
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.
López
J Cristóbal
JC
Instituto de Química Orgánica General (CSIC), Juan de la Cierva 3, 28006 Madrid, Spain. clopez@iqog.csic.es
Ventura
Juan
J
Uriel
Clara
C
Gómez
Ana M
AM
Fraser-Reid
Bert
B
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
D002241:Carbohydrates; D011725:Pyridines; D005459:Fluorides; D006858:Hydrofluoric Acid