Literature DB >> 11448670

Stereoselective synthesis of 2-S-ethyl(phenyl)-2-thio-beta-glucopyranosides via 1,2-migration and concurrent glycosidation of ethyl(phenyl) 2,3-orthoester-1-thio-alpha-mannopyranosides.

Z Yang1, B Yu.   

Abstract

1,2-Migration and concurrent glycosidation of ethyl(phenyl) 2,3-orthoester-1-thio-alpha-D- and L-mannopyranosides under the action of TMSOTf readily afforded the corresponding 2-S-ethyl(phenyl)-2-thio-beta-glucopyranosides, ready precursors to 2-deoxy-arabino-hexopyranosides (2-deoxy-beta-glucopyranosides).

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Year:  2001        PMID： 11448670     DOI： 10.1016/s0008-6215(01)00124-0

Source DB:  PubMed          Journal:  Carbohydr Res        ISSN： 0008-6215            Impact factor:   2.104


  2 in total

1.  Metal-catalyzed 1,2-shift of diverse migrating groups in allenyl systems as a new paradigm toward densely functionalized heterocycles.

Authors:  Alexander S Dudnik; Anna W Sromek; Marina Rubina; Joseph T Kim; Alexander V Kel'in; Vladimir Gevorgyan
Journal:  J Am Chem Soc       Date:  2008-01-04       Impact factor: 15.419

2.  TMSBr-mediated solvent- and work-up-free synthesis of α-2-deoxyglycosides from glycals.

Authors:  Mei-Yuan Hsu; Yi-Pei Liu; Sarah Lam; Su-Ching Lin; Cheng-Chung Wang
Journal:  Beilstein J Org Chem       Date:  2016-08-04       Impact factor: 2.883
  2 in total

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