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α‐ and β‐Glycosyl Sulfonium Ions: Generation and Reactivity
Author(s) -
Nokami Toshiki,
Shibuya Akito,
Manabe Shino,
Ito Yukishige,
Yoshida Junichi
Publication year - 2009
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.200802293
Subject(s) - sulfonium , glycosyl , chemistry , reactivity (psychology) , methanol , ion , mass spectrometry , glycoside , organic chemistry , medicinal chemistry , chromatography , salt (chemistry) , medicine , alternative medicine , pathology
Low‐temperature electrochemical oxidation of thioglycosides gave glycosyl triflates from which glycosyl sulfonium ions were produced (see scheme). The latter were characterized by NMR spectroscopy and cold‐spray mass spectrometry as a mixture of α‐ and β‐isomers (45:55). The α‐glycosyl sulfonium ion exhibited higher reactivity than the β‐glycosyl sulfonium ion in the reaction with methanol, which gave a mixture of α‐ and β‐methyl glycosides (41:59).