| S-(4-methoxyphenyl) benzenethiosulfinate (MPBT)/trifluoromethanesulfonic anhydride: a convenient system for the generation of glycosyl triflates from thioglycosides. | |
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MedLine Citation:
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PMID: 11112645 Owner: NLM Status: MEDLINE |
Abstract/OtherAbstract:
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[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. |
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Authors:
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D Crich; M Smith |
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Publication Detail:
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Type: Journal Article; Research Support, U.S. Gov't, P.H.S. |
Journal Detail:
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Title: Organic letters Volume: 2 ISSN: 1523-7060 ISO Abbreviation: Org. Lett. Publication Date: 2000 Dec |
Date Detail:
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Created Date: 2001-02-07 Completed Date: 2001-02-08 Revised Date: 2007-11-14 |
Medline Journal Info:
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Nlm Unique ID: 100890393 Medline TA: Org Lett Country: UNITED STATES |
Other Details:
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Languages: eng Pagination: 4067-9 Citation Subset: IM |
Affiliation:
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Department of Chemistry, University of Illinois at Chicago, 845 West Taylor Street, Chicago, Illinois 60607-7061, USA. dcrich@uic.edu |
Export Citation:
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APA/MLA Format Download EndNote Download BibTex |
| MeSH Terms | |
Descriptor/Qualifier:
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Benzoates
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chemistry* Magnetic Resonance Spectroscopy Mesylates / chemistry* Methylene Chloride / chemistry Solvents Thioglycosides / chemistry* |
| Grant Support | |
ID/Acronym/Agency:
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GM-57335/GM/NIGMS NIH HHS |
| Chemical | |
Reg. No./Substance:
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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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