Conversion of β-glycopyranoside to α-glycopyranoside by photo-activated radical reaction. Issue 23 (8th June 2016)

• Record Type: Journal Article
• Authors: Lai, Yu-Chen; Luo, Chin-Hung; Chou, Hsin-Chun; Yang, Cheng-Jhang; Lu, Le; Chen, Chien-Sheng
• Is Part Of: Tetrahedron letters. Volume 57:Issue 23(2016)
• Page Start: 2474
• Page End: 2477
• Publication Date: 2016-06-08
• Subjects: Radical reaction -- Quasi-anomeric effect -- Anomeric inversion -- Halogen; Chemistry, Organic -- Periodicals; 547.005
• DOI: 10.1016/j.tetlet.2016.04.064
• Languages: English
• ISSNs: 0040-4039

Abstract

Graphical abstract: Highlights: 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. Abstract: 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.