67772-73-0Relevant articles and documents
Glycosyl Fluorides as Intermediates in BF3·OEt2-Promoted Glycosylation with Trichloroacetimidates
Nielsen, Michael M.,Stougaard, Bolette A.,Bols, Mikael,Glibstrup, Emil,Pedersen, Christian M.
, p. 1281 - 1284 (2017)
Glycosyl fluorides have been found to be important intermediates in glycosylations with trichloroacetimidate donors and BF3·OEt2 activation (0.2–1 equiv.). Low-temperature NMR spectroscopy experiments revealed that the α-trichloroacetimidate was transformed into the glycosyl fluoride with inversion of stereochemistry, whereas the β anomer was not. A concerted mechanism was suggested for the stereospecific formation of glycosyl fluorides, which is not accounted for in the classic mechanism.