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Efficient High‐Yielding Syntheses and NMR Spectroscopic Studies of Some Fluorodeoxy Sugars
Author(s) -
Latif Farzana,
Malik Abdul,
Voelter Wolfgang
Publication year - 1987
Publication title -
liebigs annalen der chemie
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 0170-2041
DOI - 10.1002/jlac.198719870708
Subject(s) - chemistry , fluoride , nucleophile , organic chemistry , carbohydrate , fluorine , ring (chemistry) , catalysis , inorganic chemistry
Displacement of the triflyl group by fluoride ion in benzyl 2,3‐anhydro‐4‐ O ‐(trifluoromethylsulfonyl)pyranosides 1–3 leads with stereochemical inversion to the 4‐fluoro‐4‐deoxy sugars 4–6 , providing a general method for the introduction of fluorine in the neighborhood of an oxirane ring into anhydro sugars. This procedure is mild, high yielding, and does not experience difficulties which sometimes are encountered in nucleophilic fluoride displacements in carbohydrate systems. Detailed 1 H‐, 19 F‐, and 13 C‐NMR studies of 1–6 provided strong evidence for O H 5 conformations.