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Intermolecular aglycon transfer of ethyl thioglycosides can be prevented by judicious choice of protecting groups

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Publication date

2000-12-01

Authors

Zhu, Tong
Boons, Geert JanORCID 0000-0003-3111-5954ISNI 0000000120249047

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DOI

https://doi.org/10.1016/S0008-6215(00)00252-4

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Article

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Abstract

Unexpected intermolecular aglycon transfer occurred in chemoselective glycosylations using glycosyl fluorides or trichloroacetimidates as glycosyl donors and partially protected thioglycosides as glycosyl acceptors. It is shown that this problem can be addressed by fine-tuning of the reactivity of the anomeric thioalkyl moiety and hydroxyl of the acceptor.

Keywords

Chemoselective glycosylation, Lewis antigens, Oligosaccharide, Thioglycoside, Analytical Chemistry, Biochemistry, Organic Chemistry

Citation

Zhu, T & Boons, G J 2000, 'Intermolecular aglycon transfer of ethyl thioglycosides can be prevented by judicious choice of protecting groups', Carbohydrate Research, vol. 329, no. 4, pp. 709-715. https://doi.org/10.1016/S0008-6215(00)00252-4

URI

http://hdl.handle.net/1874/379326