Issue 24, 2011
From the journal:

Organic & Biomolecular Chemistry

Divergent synthetic approach to 6′′-modified α-GalCer analogues†

Nora Pauwels,a   Sandrine Aspeslagh,b   Gerd Vanhoenacker,c   Koen Sandra,c   Esther D. Yu,d   Dirk M. Zajonc,d   Dirk Elewaut,b   Bruno Linclaue  and  Serge Van Calenbergh*a  

* Corresponding authors

a Laboratory for Medicinal Chemistry (FFW), Faculty of Pharmaceutical Sciences, UGent, Harelbekestraat 72, B-9000 Gent, Belgium
E-mail: Serge.vancalenbergh@ugent.be
Fax: +32 9 264 81 46
Tel: +32 9 264 81 24

b Laboratory for Molecular Immunology and Inflammation, Ghent University Hospital, UGent, De Pintelaan 185, 9000 Gent, Belgium

c Research Institute for Chromatography (RIC), President Kennedypark 26, B-8500 Kortrijk, Belgium

d Division of Cell Biology, La Jolla Institute for Allergy and Immunology, 9420 Athena Circle, La Jolla, USA

e School of Chemistry, University of Southampton, Highfield, Southampton, UK

Abstract

A synthetic approach is presented for the synthesis of galacturonic acid and D-fucosyl modified KRN7000. The approach allows for late-stage functionalisation of both the sugar 6′′-OH and the sphingosine amino groups, which enables convenient synthesis of promising 6′′-modified KRN7000 analogues.

Graphical abstract: Divergent synthetic approach to 6′′-modified α-GalCer analogues

About
Cited by
Related
Download options Please wait...

Supplementary files

Article information

DOI
https://doi.org/10.1039/C1OB06235B
Article type
Paper
Submitted
23 Jul 2011
Accepted
02 Sep 2011
First published
02 Sep 2011

Org. Biomol. Chem., 2011,9, 8413-8421

Permissions

Request permissions

Divergent synthetic approach to 6′′-modified α-GalCer analogues

N. Pauwels, S. Aspeslagh, G. Vanhoenacker, K. Sandra, E. D. Yu, D. M. Zajonc, D. Elewaut, B. Linclau and S. Van Calenbergh, Org. Biomol. Chem., 2011, 9, 8413 DOI: 10.1039/C1OB06235B

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