Efficient synthesis of an alpha(2,9) trisialic acid by one-pot glycosylation and polymer-assisted deprotection

Hiroshi Tanaka; Yusuke Tateno; Yuji Nishiura; Takashi Takahashi

doi:10.1021/ol802207e

Efficient synthesis of an alpha(2,9) trisialic acid by one-pot glycosylation and polymer-assisted deprotection

Org Lett. 2008 Dec 18;10(24):5597-600. doi: 10.1021/ol802207e.

Authors

Hiroshi Tanaka¹, Yusuke Tateno, Yuji Nishiura, Takashi Takahashi

Affiliation

¹ Department of Applied Chemistry, Graduate School of Science and Engineering, Tokyo Institute of Technology, 2-12-1 Ookayama, Meguro, Tokyo 152-8552, Japan. thiroshi@apc.titech.ac.jp

PMID: 19053743
DOI: 10.1021/ol802207e

Abstract

An efficient synthesis of alpha(2,9) trisialic acid has been achieved via one-pot glycosylation and polymer-assisted deprotection. The synthesis involves chemo- and regioselective alpha-sialylation of ethylthiosialoside with the S-benzoxazolyl (S-Box) sialyl donor. Use of a prelinker to link an activated ester and a vinyl ether via a carbon chain enables polymer-assisted deprotection of the protected trisialic acids.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Glycosylation
Polymers / chemistry
Sialic Acids / chemical synthesis*

Substances

Polymers
Sialic Acids
alpha(2,9) trisialic acid