Issue 29, 2006
From the journal:

Chemical Communications

Preparation of a fluorous protecting group and its application to the chemoenzymatic synthesis of sialidase inhibitor

Kiyoshi Ikeda,*a   Hitomi Moria  and  Masayuki Sato*a  

* Corresponding authors

a Department of Organic Chemistry, School of Pharmaceutical Sciences, University of Shizuoka, 52-1 Yada Suruga-Ku, Shizuoka, Japan
E-mail: ikeda@ys2.u-shizuoka-ken.ac.jp
Fax: +81-54-264-5108
Tel: +81-54-264-5108

Abstract

2-(Perfluorohexyl)ethoxymethyl chloride was prepared as a novel fluorous protecting reagent. Neu5Ac aldolase-catalyzed chemoenzymatic transformation of N-acetyl-D-mannosamine to Neu5Ac derivatives was achieved successfully by using the fluorous reagent not only for hydroxy group protection but also for fluorous tagging. This chemoenzymatic method was applied to the synthesis of 2-deoxy-2,3-didehydrosialic acid 1 known as a potent sialidase inhibitor.

Graphical abstract: Preparation of a fluorous protecting group and its application to the chemoenzymatic synthesis of sialidase inhibitor

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Article information

DOI
https://doi.org/10.1039/B605519B
Article type
Communication
Submitted
18 Apr 2006
Accepted
19 May 2006
First published
13 Jun 2006

Chem. Commun., 2006, 3093-3094

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Preparation of a fluorous protecting group and its application to the chemoenzymatic synthesis of sialidase inhibitor

K. Ikeda, H. Mori and M. Sato, Chem. Commun., 2006, 3093 DOI: 10.1039/B605519B

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