Issue 12, 2009

Exploiting the cross-metathesis reaction in the synthesis of pseudo-oligosaccharides

Abstract

An approach to the synthesis of pseudo-oligosaccharides based on the cross-metathesis reaction between distinct sugar-olefins, followed by intramolecular cyclization of the obtained heterodimer, is presented. In particular, the relative efficiency of two alternative approaches, the straightforward cross-metathesis reaction and the two-step procedure (self-metathesis followed by cross- metathesis), was explored and compared for diverse sugar-olefin substrates. Some representative examples of intramolecular cyclization using iodine as an electrophilic promoter, are also reported.

Graphical abstract: Exploiting the cross-metathesis reaction in the synthesis of pseudo-oligosaccharides

Supplementary files

Article information

Article type
Paper
Submitted
05 Jan 2009
Accepted
30 Mar 2009
First published
05 May 2009

Org. Biomol. Chem., 2009,7, 2635-2644

Exploiting the cross-metathesis reaction in the synthesis of pseudo-oligosaccharides

P. Ronchi, S. Vignando, S. Guglieri, L. Polito and L. Lay, Org. Biomol. Chem., 2009, 7, 2635 DOI: 10.1039/B822989A

To request permission to reproduce material from this article, please go to the Copyright Clearance Center request page.

If you are an author contributing to an RSC publication, you do not need to request permission provided correct acknowledgement is given.

If you are the author of this article, you do not need to request permission to reproduce figures and diagrams provided correct acknowledgement is given. If you want to reproduce the whole article in a third-party publication (excluding your thesis/dissertation for which permission is not required) please go to the Copyright Clearance Center request page.

Read more about how to correctly acknowledge RSC content.

Social activity

Spotlight

Advertisements