Synthesis 2010(19): 3217-3242  
DOI: 10.1055/s-0030-1258228
REVIEW
© Georg Thieme Verlag Stuttgart ˙ New York

Recent Advances in the Synthesis of Carbohydrate Mimetics

Dennis C. Koester, Annika Holkenbrink, Daniel B. Werz*
Institut für Organische und Biomolekulare Chemie, Georg-August-Universität Göttingen, Tammannstraße 2, 37077 Göttingen, Germany
Fax: +49(551)399476; e-Mail: dwerz@gwdg.de;
Further Information

Publication History

Received 26 April 2010
Publication Date:
25 August 2010 (online)

Abstract

Highly diverse strategies are employed to mimic carbohydrates. Two subgroups of carbohydrate mimetics are very important: alterations of the core structure and modifications of the O-glycosidic linkage. This review presents methods, most of them developed in the 21st century, to mimic carbohydrates with a focus on their synthesis. A wide range of different reactions are discussed in order to access carbohydrate-like structures.

1 Introduction

1.1 Scope of the Review

2 Core Modifications

2.1 Modifications of Functional Groups

2.1.1 Additional Alkyl Substituents

2.1.2 Fluorine Substituents

2.2 Seven-Membered Rings

3 Linkage Modifications

3.1 N-Glycosides

3.2 S-Glycosides

3.3 C-Glycosides

3.4 Peptoidic Bonds

4 Miscellaneous

5 Conclusion and Outlook

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Jaradat, D. M. M.; Hamouda, H.; Hackenberger, C. P. R. Eur. J. Org. Chem. 2010, DOI: 10.1002/ejoc.201000627.