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Ready Transformation of Partially Unprotected Thioglycosides into Glycosyl Fluorides Mediated by NIS/HF–Pyridine or Et 3 N·3HF
Author(s) -
López J. Cristóbal,
BernalAlbert Paloma,
Uriel Clara,
Gómez Ana M.
Publication year - 2008
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.200800754
Subject(s) - chemistry , pyridine , glycosyl , fluoride , triethylamine , hydrogen fluoride , medicinal chemistry , transformation (genetics) , tris , organic chemistry , inorganic chemistry , biochemistry , gene
The transformation of partially unprotected phenyl 1‐thioglycosides into glycosyl fluorides can be conveniently carried out by treatment with NIS in the presence of HF–pyridine. Other sources of halonium ions such as NBS, IDCP, have also been employed. The combination NIS/Et 3 N · 3HF, where triethylamine–tris(hydrogen fluoride) (Et 3 N · 3HF) replaces HF–pyridine, can also effect this transformation when acid‐sensitive substituents are present. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2008)