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

Gundeboina Narasimha; Batthula Srinivas; Palakodety Radha Krishna; Sudhir Kashyap

doi:10.1055/s-0033-1340552

Synlett, Inhaltsverzeichnis

Synlett 2014; 25(4): 523-526
DOI: 10.1055/s-0033-1340552

letter

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

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

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Abstract

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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.

Key words

glycosylation - glycosides - stereoselective synthesis - Ferrier reaction - glycal

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Referenzen

References and Notes

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Zusatzmaterial

Supporting Information