Efficient synthesis of a 6-deoxy-talose containing tetrasccharide found in Franconibacter helveticus LMG23732T. (2nd May 2018)

• Record Type: Journal Article
• Authors: Xu, Yiren; Xu, Tianheng; Zhang, Jianjun
• Is Part Of: Carbohydrate research. Volume 460(2018)
• Page Start: 57
• Page End: 65
• Publication Date: 2018-05-02
• Subjects: Franconibacter helveticus -- Lipopolysaccharides -- O-specific polysaccharide -- Tetrasaccharide -- Synthesis; 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.2018.01.002
• Languages: English
• ISSNs: 0008-6215

Abstract

Abstract: Synthesis of the 6-deoxy-talose (6-dTal) containing tetrasaccharide, naturally found in Franconibacter helveticus LMG23732T, has been described. The synthetic method utilized an allyloxyethylidene group for protecting the 1-OH and 2-OH groups of rhamnopyranose and a redox reaction for synthesizing 6-deoxy talose, which eventually formed a disaccharide containing α-Glc p -(1→2)-6dTal p configured glycosidic bonds using a [2 + 2] synthetic strategy. Graphical abstract: Highlights: We have reported a convergent total synthesis of a tetrasccharide analogue. Stereo- and regio-specific synthesis was achieved in Schmidt glycosylation employing protected L-talopyranosyl and D-glucopyranosyl building blocks. The synthesis involves an allyloxyethylidene group and a redox reaction of rhamnopyranoside derivative for the synthesis of 6-deoxy talopyranoside.