Issue 16, 2010

Recent advances in stereoselective glycosylation through intramolecular aglycon delivery

Abstract

Methodology toward the stereoselective 1,2-cis glycoside linkage using intramolecular aglycon delivery (IAD) has been extensively developed. In the last two decades, progress has been made using various mixed acetal linkages and a number of glycosyl donor moieties to develop novel IAD strategies, mainly based on formation of acetal linkages. This account summarizes the newest naphthylmethyl (NAP) ether-mediated IAD as well as all the types of mediations for stereospecific construction of various 1,2-cis linkages, not only for β-mannopyranoside, but also for other linkages almost without exception, including β-L-rhamnoside.

Graphical abstract: Recent advances in stereoselective glycosylation through intramolecular aglycon delivery

Article information

Article type
Perspective
Submitted
17 Mar 2010
First published
28 Jun 2010

Org. Biomol. Chem., 2010,8, 3596-3608

Recent advances in stereoselective glycosylation through intramolecular aglycon delivery

A. Ishiwata, Y. J. Lee and Y. Ito, Org. Biomol. Chem., 2010, 8, 3596 DOI: 10.1039/C004281A

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