Literature DB >> 19398332

(S)-Camphorsulfonic acid catalyzed highly stereoselective synthesis of pseudoglycosides.

Bala Kishan Gorityala1, Shuting Cai, Jimei Ma, Xue-Wei Liu.   

Abstract

A mild and efficient synthesis of pseudoglycosides has been developed using metal free (S)-camphorsulfonic acid. (S)-CSA acts as an excellent catalyst for conversion of 2,4,6-tri-O-acetyl-D-glucal to 2,3-unsaturated O-glycosides. A wide range of biologically active natural products, alcohols and thiols could be coupled with glucal to give the desired pseudoglycosides in good to excellent yields with exclusive alpha-stereoselectivity.

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Year:  2009        PMID: 19398332     DOI: 10.1016/j.bmcl.2009.04.003

Source DB:  PubMed          Journal:  Bioorg Med Chem Lett        ISSN: 0960-894X            Impact factor:   2.823


  2 in total

Review 1.  Chemical O-Glycosylations: An Overview.

Authors:  Rituparna Das; Balaram Mukhopadhyay
Journal:  ChemistryOpen       Date:  2016-08-17       Impact factor: 2.911

2.  Cyanuric chloride as an efficient catalyst for the synthesis of 2,3-unsaturated O-glycosides by Ferrier rearrangement.

Authors:  Xiaojuan Yang; Na Li
Journal:  ScientificWorldJournal       Date:  2014-01-19
  2 in total

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