Synlett 2014; 25(4): 523-526
DOI: 10.1055/s-0033-1340552
letter
© Georg Thieme Verlag Stuttgart · New York

Zn(OTf)2-Catalyzed Glycosylation of Glycals: Synthesis of 2,3-Unsaturated Glycosides via a Ferrier Reaction

Authors

  • Gundeboina Narasimha

    D-207, Discovery Laboratory, Organic and Biomolecular Chemistry Division, CSIR-Indian Institute of Chemical Technology, Hyderabad 500 007, India   Fax: +91(40)27160387   Email: skashyap@iict.res.in
  • Batthula Srinivas

    D-207, Discovery Laboratory, Organic and Biomolecular Chemistry Division, CSIR-Indian Institute of Chemical Technology, Hyderabad 500 007, India   Fax: +91(40)27160387   Email: skashyap@iict.res.in
  • Palakodety Radha Krishna*

    D-207, Discovery Laboratory, Organic and Biomolecular Chemistry Division, CSIR-Indian Institute of Chemical Technology, Hyderabad 500 007, India   Fax: +91(40)27160387   Email: skashyap@iict.res.in
  • Sudhir Kashyap*

    D-207, Discovery Laboratory, Organic and Biomolecular Chemistry Division, CSIR-Indian Institute of Chemical Technology, Hyderabad 500 007, India   Fax: +91(40)27160387   Email: skashyap@iict.res.in
Further Information

Publication History

Received: 07 November 2013

Accepted after revision: 09 December 2013

Publication Date:
14 January 2014 (online)


Graphical Abstract

Preview

Abstract

A mild, catalytic, and efficient protocol has been developed for the synthesis of 2,3-unsaturated glycosides or ‘pseudo-glycals’ using Zn(OTf)2. Stereoselective glycosylation of glycal donor with various acceptors comprising of alcohols, phenols, thiols, and sugar aglycones proceeds smoothly to afford the corresponding 2,3-unsaturaed glycosides in good to excellent yields.

Supporting Information