Issue 48, 2012
From the journal:

Organic & Biomolecular Chemistry

Convergent stereoselective synthesis of multiple sulfated GlcNα(1,4)GlcAβ(1,4) dodecasaccharides†

Hiroshi Tanaka,*a   Yusuke Tatenoa  and  Takashi Takahashi*a  

* Corresponding authors

a Department of Applied Chemistry, Graduate School of Science and Engineering, Tokyo Institute of Technology, 2-12-1-H-101 Ookayama, Meguro, Japan
E-mail: thiroshi@apc.titech.ac.jp
Fax: +81-3-5734-2884
Tel: +81-3-5734-2471

Abstract

In this paper, we describe an effective method for the elongation of a GlcNα(1,4)GlcAβ(1,4) sequence using a GlcNTrocα(1,4)GlcA disaccharide unit and the synthesis of the N- and/or O-sulfated GlcNα(1,4)GlcAβ(1,4) oligosaccharides. N-Troc protection of GlcNα(1,4)GlcA units was effective for the synthesis of the GlcNα(1,4)GlcAβ(1,4) oligosaccharides in comparison with the azido substituent. The GlcNα(1,4)GlcAβ(1,4) dodecasaccharide was successfully prepared by the direct β-selective glycosidation of glucuronate in the GlcNα(1,4)GlcAβ(1,4)GlcNα(1,4)GlcAβ(1,4) tetrasaccharide. In addition, the synthesis of the N- and/or O-sulfated GlcNα(1,4)GlcAβ(1,4) oligosaccharides was accomplished by fluorous-assisted deprotection and sulfation. The fluorous-assisted synthetic technology applied to the highly polar sulfated oligosaccharide permits it to be more easily separated from the highly polar reagents, such as SO3·NEt3.

Graphical abstract: Convergent stereoselective synthesis of multiple sulfated GlcNα(1,4)GlcAβ(1,4) dodecasaccharides

About
Cited by
Related
Download options Please wait...

Supplementary files

Article information

DOI
https://doi.org/10.1039/C2OB26928G
Article type
Paper
Submitted
01 Oct 2012
Accepted
17 Oct 2012
First published
19 Oct 2012

Org. Biomol. Chem., 2012,10, 9570-9582

Permissions

Request permissions

Convergent stereoselective synthesis of multiple sulfated GlcNα(1,4)GlcAβ(1,4) dodecasaccharides

H. Tanaka, Y. Tateno and T. Takahashi, Org. Biomol. Chem., 2012, 10, 9570 DOI: 10.1039/C2OB26928G

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