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. 2016 Sep 2;18(17):4222-5.
doi: 10.1021/acs.orglett.6b01962. Epub 2016 Aug 16.

Stereoselective Glycosylation of 2-Nitrogalactals Catalyzed by a Bifunctional Organocatalyst

Sandra Medina  1 , Matthew J Harper  1 , Edward I Balmond  1 , Silvia Miranda  1 , Giacomo E M Crisenza  1 , Diane M Coe  2 , Eoghan M McGarrigle  3 , M Carmen Galan  1
Affiliations

Stereoselective Glycosylation of 2-Nitrogalactals Catalyzed by a Bifunctional Organocatalyst

Sandra Medina et al. Org Lett. .

Abstract

The use of a bifunctional cinchona/thiourea organocatalyst for the direct and α-stereoselective glycosylation of 2-nitrogalactals is demonstrated for the first time. The conditions are mild, practical, and applicable to a wide range of glycoside acceptors with products being isolated in good to excellent yields. The method is exemplified in the synthesis of mucin type Core 6 and 7 glycopeptides.

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Conflict of interest statement

The authors declare no competing financial interest.

Figures

Figure 1
Figure 1
Proposed general activation of nitroalkenes by bifunctional thiourea catalysts.
Scheme 1
Scheme 1. Synthesis of Mucin-Type Core 6 and 7 Glycosides 10 and 13
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