Document Detail

Alpha- and beta-glycosyl sulfonium ions: generation and reactivity.
MedLine Citation:
PMID:  19156648     Owner:  NLM     Status:  MEDLINE    
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 alpha- and beta-isomers (45:55). The alpha-glycosyl sulfonium ion exhibited higher reactivity than the beta-glycosyl sulfonium ion in the reaction with methanol, which gave a mixture of alpha- and beta-methyl glycosides (41:59).
Toshiki Nokami; Akito Shibuya; Shino Manabe; Yukishige Ito; Jun-ichi Yoshida
Publication Detail:
Type:  Journal Article; Research Support, Non-U.S. Gov't    
Journal Detail:
Title:  Chemistry (Weinheim an der Bergstrasse, Germany)     Volume:  15     ISSN:  1521-3765     ISO Abbreviation:  Chemistry     Publication Date:  2009  
Date Detail:
Created Date:  2009-02-24     Completed Date:  2009-06-05     Revised Date:  2009-08-04    
Medline Journal Info:
Nlm Unique ID:  9513783     Medline TA:  Chemistry     Country:  Germany    
Other Details:
Languages:  eng     Pagination:  2252-5     Citation Subset:  IM    
Department of Synthetic Chemistry and Biological Chemistry, Graduate School of Engineering Kyoto University, Nishikyo-ku, Kyoto 615-8510, Japan.
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MeSH Terms
Cold Temperature
Glucose / analogs & derivatives,  chemistry
Magnetic Resonance Spectroscopy
Mesylates / chemical synthesis,  chemistry
Sulfonium Compounds / chemical synthesis,  chemistry*
Thioglycosides / chemistry*
Reg. No./Substance:
0/Mesylates; 0/Sulfonium Compounds; 0/Thioglycosides; 50-99-7/Glucose

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