Conversion of β-glycopyranoside to α-glycopyranoside by photo-activated radical reaction

[Display omitted] •Invert the glycosidic bond by photo-activated chlorine radical.•Chlorine radical generated from carbon tetrachloride is more active than that from NCS with BF3·OEt2 as Lewis acid.•Quasi anomeric effect is applied to explain α-regioselectivity for radical anomeric inversion. By usi...

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Bibliographic Details
Published in:Tetrahedron letters 2016-06, Vol.57 (23), p.2474-2477
Main Authors: Lai, Yu-Chen, Luo, Chin-Hung, Chou, Hsin-Chun, Yang, Cheng-Jhang, Lu, Le, Chen, Chien-Sheng
Format: Article
Language:English
Subjects:
Anomeric inversion
Halogen
Quasi-anomeric effect
Radical reaction
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Summary:[Display omitted] •Invert the glycosidic bond by photo-activated chlorine radical.•Chlorine radical generated from carbon tetrachloride is more active than that from NCS with BF3·OEt2 as Lewis acid.•Quasi anomeric effect is applied to explain α-regioselectivity for radical anomeric inversion. By using carbon tetrachloride as the chloride radical and boron trifluoride etherate as the Lewis acid, the halogen-light-activated anomeric inversion of glycoside was achieved. This reaction is a novel guide to invert the glycosidic bond from a β-anomer to an α-anomer.
ISSN:0040-4039
1873-3581
DOI:10.1016/j.tetlet.2016.04.064