Photocatalyzed Decarboxylative Thio(seleno)etherification of Redox-Active Uronates Enables Synthesis of Rare Sugar
Xinxin Zhang1, Han Ding2, Jinping Zhang1
1Key Laboratory of Marine Drugs of Ministry of Education, Shandong Key Laboratory of Glycoscience and Glycotherapeutics, School of Medicine and Pharmacy, Ocean University of China, Qingdao 266003, China.
Abstract:
Rare sugar-based thio(seleno)glycosides are synthetically and biologically important yet challenging-to-prepare synthons. We here present a novel approach to such constructs from readily available C-glycosides with photocatalyzed decarboxylative thio(seleno)etherification of redox-active uronates as the key transformation following a C1-to-C5 switch strategy. This protocol tolerates diverse substrates and various protecting groups, stereoselectively affording the desirable thio(seleno)glycosides in moderate-to-high yields. The power of this method is demonstrated by the successful assembly of a 1,7-S-linked trisaccharide composed of α-d-ido-heptopyranosyl units.
More Related Videos
12:30Synthesis of a Thiol Building Block for the Crystallization of a Semiconducting Gyroidal Metal-sulfur Framework
Published on: April 9, 2018
08:47Synthesis and Bioconjugation of Thiol-Reactive Reagents for the Creation of Site-Selectively Modified Immunoconjugates
Published on: March 6, 2019
Related Concept Videos
Preparation and Reactions of Sulfides
Preparation and Reactions of Thiols
Oxidation of Alkenes: Syn Dihydroxylation with Osmium Tetraoxide
Synthesis of α-Substituted Carbonyl Compounds: The Stork Enamine Reaction
Preparation of Nitriles
Reduction of Alkenes: Asymmetric Catalytic Hydrogenation
The metal catalyst used can be either heterogeneous or homogeneous. When hydrogenation of an alkene generates a chiral center, a pair of enantiomeric products is expected to form. However, an enantiomeric excess of one of the products can be facilitated using an enantioselective reaction or an...
