Issue 23, 2012
From the journal:

RSC Advances

Stereoselective synthesis of C-2-methylene and C-2-methyl-C-glycosides by Claisen rearrangement of 2-vinyloxymethyl glycals†

Perali Ramu Sridhar*a  and  Chalapala Sudharania  

* Corresponding authors

a School of Chemistry, University of Hyderabad, Hyderabad-500 046, India
E-mail: prssc@uohyd.ernet.in
Fax: +91 4023012460
Tel: +91 4066794823

Abstract

An efficient protocol for the stereoselective synthesis of C-2-methylene-α- and -β-C-glycosides by a Claisen rearrangement of 2-vinyloxymethyl glycal derivatives is reported. A plausible mechanism for the formation of α-selective-C-glycoside was proposed. The methodology was further extended to the high diastereoselective synthesis of C-2-methyl-C-glycosides.

Graphical abstract: Stereoselective synthesis of C-2-methylene and C-2-methyl-C-glycosides by Claisen rearrangement of 2-vinyloxymethyl glycals

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Article information

DOI
https://doi.org/10.1039/C2RA21505E
Article type
Communication
Submitted
19 Jul 2012
Accepted
29 Jul 2012
First published
30 Jul 2012

RSC Adv., 2012,2, 8596-8598

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Stereoselective synthesis of C-2-methylene and C-2-methyl-C-glycosides by Claisen rearrangement of 2-vinyloxymethyl glycals

P. R. Sridhar and C. Sudharani, RSC Adv., 2012, 2, 8596 DOI: 10.1039/C2RA21505E

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