Document Detail


S-(4-methoxyphenyl) benzenethiosulfinate (MPBT)/trifluoromethanesulfonic anhydride: a convenient system for the generation of glycosyl triflates from thioglycosides.
MedLine Citation:
PMID:  11112645     Owner:  NLM     Status:  MEDLINE    
Abstract/OtherAbstract:
[structure] The combination of S-(4-methoxyphenyl) benzenethiosulfinate (MPBT, 1) and trifluoromethanesulfonic anhydride forms a powerful, metal-free, thiophile which readily activates thioglycosides, via glycosyl triflates, at -60 degrees C in dichloromethane, in the presence of 2,6-di-tert-butyl-4-methylpyridine. The glycosyl triflates are rapidly and cleanly converted to glycosides, upon treatment with alcohols, in good yield and selectivity.
Authors:
D Crich; M Smith
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Publication Detail:
Type:  Journal Article; Research Support, U.S. Gov't, P.H.S.    
Journal Detail:
Title:  Organic letters     Volume:  2     ISSN:  1523-7060     ISO Abbreviation:  Org. Lett.     Publication Date:  2000 Dec 
Date Detail:
Created Date:  2001-02-07     Completed Date:  2001-02-08     Revised Date:  2007-11-14    
Medline Journal Info:
Nlm Unique ID:  100890393     Medline TA:  Org Lett     Country:  UNITED STATES    
Other Details:
Languages:  eng     Pagination:  4067-9     Citation Subset:  IM    
Affiliation:
Department of Chemistry, University of Illinois at Chicago, 845 West Taylor Street, Chicago, Illinois 60607-7061, USA. dcrich@uic.edu
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MeSH Terms
Descriptor/Qualifier:
Benzoates / chemistry*
Magnetic Resonance Spectroscopy
Mesylates / chemistry*
Methylene Chloride / chemistry
Solvents
Thioglycosides / chemistry*
Grant Support
ID/Acronym/Agency:
GM-57335/GM/NIGMS NIH HHS
Chemical
Reg. No./Substance:
0/Benzoates; 0/Mesylates; 0/Solvents; 0/Thioglycosides; 0/methylamino-2-phenyl-2-butyl-3,4,5-trimethoxybenzoate; 1493-13-6/trifluoromethanesulfonic acid; 75-09-2/Methylene Chloride

From MEDLINE®/PubMed®, a database of the U.S. National Library of Medicine


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