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Synlett 2017; 28(16): 2131-2134
DOI: 10.1055/s-0036-1588478
letter
© Georg Thieme Verlag Stuttgart · New York

Fluoropyridyl Sugars – Masked Imidate Glycosyl Donors that Display Reactivity, Selectivity, and Stability

Ray Leslie*
Department of Chemistry, Nottingham Trent University, Clifton Lane, Nottingham, NG11 8NS, UK   Email: raymond.leslie@ntu.ac.uk
,
Kavnen Tseke
Department of Chemistry, Nottingham Trent University, Clifton Lane, Nottingham, NG11 8NS, UK   Email: raymond.leslie@ntu.ac.uk
,
Agneta Vitkute
Department of Chemistry, Nottingham Trent University, Clifton Lane, Nottingham, NG11 8NS, UK   Email: raymond.leslie@ntu.ac.uk
,
Sophie L. Benjamin
Department of Chemistry, Nottingham Trent University, Clifton Lane, Nottingham, NG11 8NS, UK   Email: raymond.leslie@ntu.ac.uk
,
L. Nitin Seetohul
Department of Chemistry, Nottingham Trent University, Clifton Lane, Nottingham, NG11 8NS, UK   Email: raymond.leslie@ntu.ac.uk
› Author Affiliations
Further Information

Publication History

Received: 01 June 2017

Accepted: 01 June 2017

Publication Date:
11 July 2017 (online)

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Abstract

Fluoropyridyl glycosides, synthesized from the corresponding glycosyl bromides, are shown to be excellent donors in glycosylation reactions. Both armed and disarmed donors were prepared and reacted smoothly with a series of glycosyl acceptors. Coupling proceeded in high yields, with activation of the donor achieved using a range of promoters, and also displayed unusually high selectivity. In addition these novel systems offer the potential for introducing a series of glycosyl donors with ‘tunable reactivity’.

Key words

fluoropyridyl - masked imidate - donors - glycosylation - stereoselectivity

Supporting Information

    Supporting information for this article is available online at https://doi.org/10.1055/s-0036-1588478.
  • Supporting Information
 

  • References and Notes

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