Photoinitiated hydrothiolation of pyranoid exo-glycals: the d-galacto and d-xylo cases. (2nd September 2015)

• Record Type: Journal Article
• Authors: József, János; Juhász, László; Illyés, Tünde Zita; Csávás, Magdolna; Borbás, Anikó; Somsák, László
• Is Part Of: Carbohydrate research. Volume 413(2015)
• Page Start: 63
• Page End: 69
• Publication Date: 2015-09-02
• Subjects: Thiol-ene click reaction -- Exo-galactal -- Exo-xylal -- Disaccharide mimicks; 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.2015.05.008
• Languages: English
• ISSNs: 0008-6215

Abstract

Abstract: Radical-mediated addition reactions of thiols to O -peracetylated exo -galactal and exo -xylal with 2, 2-dimethoxy-2-phenylacetophenone as the photoinitiator resulted in high yielding formation of the corresponding β-d -glycopyranosylmethyl-sulfide derivatives (2, 6-anhydro-1-deoxy-1- S -substituted-1-thio-alditols) with exclusive regio- and very high stereoselectivity, including disaccharide mimicks with Gly-CH2 -S-Gly scaffolds. Graphical abstract: Highlights: Photoinitiated thiol-ene reaction of O -peracetylated exo -glycals. Synthesis of β-d -glycopyranosylmethyl-sulfide type glycomimetics. Exclusive regio- and stereoselectivity with exo -galactal. Exclusive regio- and very high stereoselectivity with exo -xylal. Disaccharide mimicks of Gly-CH2 -S-Gly scaffolds.