Literature DB >> 11428018

Stereoselective synthesis of 2-S-phenyl-2-deoxy-beta-glycosides using phenyl 2,3-O-thionocarbonyl-1-thioglycoside donors via 1,2-Migration and concurrent glycosidation.

B Yu1, Z Yang.   

Abstract

[figure: see text] 1,2-Migration and concurrent glycosidation of phenyl 2,3-O-thionocarbonyl-1-thlo-alpha-L-rhamnopyranosides under the action of methyl trifluoromethanesulfonate (MeOTf) afforded in high yields the 3-O-(methylthio)carbonyl-2-S-phenyl-2,6-dideoxy-beta-L-glucopyranosides, ready precursors to the corresponding 2-deoxy-beta-glycosides.

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Year:  2001        PMID: 11428018     DOI: 10.1021/ol006894+

Source DB:  PubMed          Journal:  Org Lett        ISSN: 1523-7052            Impact factor:   6.005


  4 in total

1.  Sulfur Transfer Versus Phenyl Ring Transfer in the Gas Phase: Sequential Loss of CH3OH and CH3O-P=O from Protonated Phosphorothioates.

Authors:  Xiaoping Zhang; Honghan Chen; Yin Ji; Kezhi Jiang; Huanwen Chen
Journal:  J Am Soc Mass Spectrom       Date:  2018-12-19       Impact factor: 3.109

2.  1,2-Migration of the thio group in allenyl sulfides: efficient synthesis of 3-thio-substituted furans and pyrroles.

Authors:  Joseph T Kim; Alexander V Kel'in; Vladimir Gevorgyan
Journal:  Angew Chem Int Ed Engl       Date:  2003-01-03       Impact factor: 15.336

3.  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

4.  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

  4 in total

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