α‐ and β‐Glycosyl Sulfonium Ions: Generation and Reactivity | Zendy

Nokami Toshiki | Zendy; Shibuya Akito | Zendy; Manabe Shino | Zendy; Ito Yukishige | Zendy; Yoshida Junichi | Zendy

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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).

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