Gold(I)-catalyzed synthesis of β-Kdo glycosides using Kdo ortho-hexynylbenzoate as donor. (7th August 2017)

• Record Type: Journal Article
• Authors: Mi, Xuemeng; Lou, Qixin; Fan, Wenjing; Zhuang, Liqin; Yang, You
• Is Part Of: Carbohydrate research. Volume 448(2017)
• Page Start: 161
• Page End: 165
• Publication Date: 2017-08-07
• Subjects: Glycosylation -- Gold -- Kdo -- Glycosyl ortho-hexynylbenzoate -- Synthetic methods; Carbohydrates -- Periodicals; Chemistry, Organic -- Periodicals; Biochemistry -- Periodicals; Carbohydrates -- Periodicals; Chimie organique -- Périodiques; Glucides -- Périodiques; Biochemistry; Carbohydrates; Chemistry, Organic; Periodicals; Electronic journals; 507.78
• DOI: 10.1016/j.carres.2017.04.021
• Languages: English
• ISSNs: 0008-6215

Abstract

Abstract: A gold(I)-catalyzed glycosylation of Kdo with glycosyl ortho -hexynylbenzoate as donor is reported. The couplings of Kdo ortho -hexynylbenzoate with a set of alcohols promoted by PPh3 AuOTf afford Kdo glycosides with good β-selectivities. This glycosylation method allows for the synthesis of β-Kdo monosaccharide with a C5 linker at the reducing end for subsequent conjugation to carrier proteins and arrays. Graphical abstract: Highlights: A gold(I)-catalyzed glycosylation with Kdo ortho -hexynylbenzoate as donor is described. The Kdo glycosides were obtained with excellent β-selectivities. Synthesis of β-Kdo monosaccharide with a C5 linker at the reducing end is achieved.