title: Photoinitiated hydrothiolation of pyranoid exo-glycals: the d-galacto and d-xylo cases.
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.
authors.affiliation: Department of Organic Chemistry, PO Box 20, University of Debrecen, H-4010 Debrecen, Hungary.
authors.forename: János
authors.initials: J
authors.lastname: József
authors.affiliation: Department of Organic Chemistry, PO Box 20, University of Debrecen, H-4010 Debrecen, Hungary.
authors.forename: László
authors.initials: L
authors.lastname: Juhász
authors.affiliation: Department of Organic Chemistry, PO Box 20, University of Debrecen, H-4010 Debrecen, Hungary.
authors.forename: Tünde Zita
authors.initials: TZ
authors.lastname: Illyés
authors.affiliation: Department of Pharmaceutical Chemistry, PO Box 78, University of Debrecen, H-4010 Debrecen, Hungary.
authors.forename: Magdolna
authors.initials: M
authors.lastname: Csávás
authors.affiliation: Department of Pharmaceutical Chemistry, PO Box 78, University of Debrecen, H-4010 Debrecen, Hungary.
authors.forename: Anikó
authors.initials: A
authors.lastname: Borbás
authors.affiliation: Department of Organic Chemistry, PO Box 20, University of Debrecen, H-4010 Debrecen, Hungary. Electronic address: somsak.laszlo@science.unideb.hu.
authors.forename: László
authors.initials: L
authors.lastname: Somsák
mesh_terms: D040761:Biomimetic Materials / Q000737:chemistry*; D005690:Galactose / Q000737:chemistry*; D055668:Photochemical Processes; D013237:Stereoisomerism; D013438:Sulfhydryl Compounds / Q000737:chemistry*; D013440:Sulfides / Q000737:chemistry; D014994:Xylose / Q000737:chemistry*
chemical_list: D013438:Sulfhydryl Compounds; D013440:Sulfides; D014994:Xylose; D005690:Galactose
keywords: Disaccharide mimicks; Exo-galactal; Exo-xylal; Thiol-ene click reaction