C-2 auxiliaries for stereoselective glycosylation based on common additive functional groups
Frank F J de Kleijne1, Sam J Moons1, Paul B White1
1Institute for molecules and materials, Nijmegen, 6525AJ, Netherlands. t.boltje@science.ru.nl.
Abstract:
The stereoselective introduction of the glycosidic bond is one of the main challenges in chemical oligosaccharide synthesis. Stereoselective glycosylation can be achieved using neighbouring group participation of a C-2 auxiliary or using additives, for example. Both methods aim to generate a defined reactive intermediate that reacts in a stereoselective manner with alcohol nucleophiles. This inspired us to develop new C-2 auxiliaries based on commonly used additive functionalities such as ethers, phosphine oxides and tertiary amides. Good 1,2-trans-selectivity was observed for the phosphine oxide and amide-based auxiliaries expanding the toolbox with new auxiliaries for stereoselective glycosylation reactions.
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