A Convergent Synthetic Strategy towards Oligosaccharides containing 2, 3, 6‐Trideoxypyranoglycosides. Issue 2 (6th December 2018)

• Record Type: Journal Article
• Authors: Lee, Juyeol; Kang, Soyeong; Kim, Jungjoon; Moon, Dohyun; Rhee, Young Ho
• Is Part Of: Angewandte Chemie international edition. Volume 58:Issue 2(2019)
• Page Start: 628
• Page End: 631
• Publication Date: 2018-12-06
• Subjects: asymmetric synthesis -- carbohydrates -- diastereoselectivity -- oligosaccharides -- palladium; Chemistry -- Periodicals; 540
• DOI: 10.1002/anie.201812222
• Languages: English
• ISSNs: 1433-7851

Abstract

Abstract: A de novo synthetic strategy for the production of oligosaccharides containing 2, 3, 6‐trideoxypyranoglycoside is reported. The key event is the Pd‐catalyzed asymmetric diastereoselective hydroalkoxylation of ene‐alkoxyallene‐linked glycosidic fragments. The utility of this approach was demonstrated by the activation‐free, stereodivergent, and convergent synthesis of various 2‐deoxyoligosaccharides, as well as their aglycon conjugates. Abstract : Short and sweet : A synthetic strategy for the production of 2, 3, 6‐trideoxyoligosaccharide is described. The key to this strategy is the use of an ene‐alkoxyallene moiety possessing a glycosidic unit. The utility of the reaction was demonstrated by synthesizing a number of 2, 3, 6‐trideoxyoligosaccharides, including a tetrasaccharide moiety found in landomycin Y.