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. 2011 Oct 14;47(38):10602-4.
doi: 10.1039/c1cc13409d. Epub 2011 Sep 5.

Reverse orthogonal strategy for oligosaccharide synthesis

Kohki Fujikawa  1 , N Vijaya Ganesh, Yih Horng Tan, Keith J Stine, Alexei V Demchenko
Affiliations

Reverse orthogonal strategy for oligosaccharide synthesis

Kohki Fujikawa et al. Chem Commun (Camb). .

Abstract

Herein, we report the invention of a novel expeditious concept for oligosaccharide synthesis. Unlike the classic orthogonal strategy based on leaving groups, the reverse approach is based on orthogonal protecting groups, herein p-methoxybenzyl and 4-pentenoyl, which allows for efficient oligosaccharide assembly in the reverse direction.

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Figures

Scheme 1
Scheme 1
(a) Conventional linear synthesis involving separate glycosylation and deprotection steps. (b) Ogawa’s leaving group-based orthogonal strategy. (c) New reverse orthogonal concept based on orthogonal protecting groups.
Scheme 2
Scheme 2
Four-step synthesis of pentasaccharide 6 via the reverse orthogonal strategy.
Scheme 3
Scheme 3
Preliminary investigation of secondary glycosyl acceptors 7a and 7b.
See this image and copyright information in PMC

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