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Issue 11, 2016
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2,3-Di-O-picolinyl building blocks as glycosyl donors with switchable stereoselectivity

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Abstract

2-O-Picolinyl protected glycosyl donors lead to the formation of 1,2-trans glycosides with complete stereoselectivity. This is due to the participatory effect of the picolinyl nitrogen that is able to block the bottom face of the ring via a six-membered cyclic intermediate. Herein we demonstrate that if the nitrogen atom of the O-picolinyl moiety is temporarily blocked by coordination to the metal center (Pd), it becomes unavailable to participate in glycosylation and hence the stereoselectivity of 2-O-picolinyl-assisted glycosylations can be “switched”.

Graphical abstract: 2,3-Di-O-picolinyl building blocks as glycosyl donors with switchable stereoselectivity

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Supplementary files

Publication details

The article was received on 14 Jan 2016, accepted on 12 Feb 2016 and first published on 12 Feb 2016


Article type: Paper
DOI: 10.1039/C6OB00107F
Org. Biomol. Chem., 2016,14, 3159-3169

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    2,3-Di-O-picolinyl building blocks as glycosyl donors with switchable stereoselectivity

    J. P. Yasomanee, A. R. Parameswar, P. Pornsuriyasak, N. P. Rath and A. V. Demchenko, Org. Biomol. Chem., 2016, 14, 3159
    DOI: 10.1039/C6OB00107F

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