Preparation of S-glycoside surfactants and cysteine thioglycosides using minimally competent Lewis acid catalysis. (3rd March 2016)

• Record Type: Journal Article
• Authors: Szabó, Lajos Z.; Hanrahan, Dillon J.; Jones, Evan M.; Martin, Erin; Pemberton, Jeanne E.; Polt, Robin
• Is Part Of: Carbohydrate research. Volume 422(2016)
• Page Start: 1
• Page End: 4
• Publication Date: 2016-03-03
• Subjects: Thioglycoside -- S-glycosidic linkage -- Glycolipid -- InBr3 -- Surfactant -- Glycosylated cysteine; 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.2015.12.008
• Languages: English
• ISSNs: 0008-6215

Abstract

Highlights: Thioglycosides can be readily prepared from per- acetylated carbohydrate donors. S-Glycosylations are catalyzed using the minimally competent Lewis acid InBr3 . Only β anomers are formed. Glycosylation of cysteine and a library of thio-glycolipids are produced by Zemplèn deacylation. Graphical abstract: Abstract: Here we report a method for the preparation of anomerically pure β-S-glycopyranosides (1, 2- trans- glycosides) from the corresponding peracetate donors. S-glycosylation was performed in CHCl3 at reflux in the presence of a catalytic amount of InBr3 . Deacylation of the intermediate peracetates were achieved under Zemplén conditions. Five pyranose examples, monosaccharides D-glucose and D-galactose and disaccharides cellobiose, maltose, and lactose, were used as donors, and five thiols including an α/ω dithiol and Fmoc-L-cysteine were used as acceptors. Melting points, high res MS, [α]D and NMR data ( 1 H and 13 C, including COSY, HSQC and HMBC) are reported for compounds not previously described.