Photoinitiated hydrothiolation of pyranoid exo-glycals: the d-galacto and d-xylo cases

János József; László Juhász; Tünde Zita Illyés; Magdolna Csávás; Anikó Borbás; László Somsák

doi:10.1016/j.carres.2015.05.008

Photoinitiated hydrothiolation of pyranoid exo-glycals: the d-galacto and d-xylo cases

Carbohydr Res. 2015 Sep 2:413:63-9. doi: 10.1016/j.carres.2015.05.008. Epub 2015 Jun 3.

Authors

János József¹, László Juhász¹, Tünde Zita Illyés¹, Magdolna Csávás², Anikó Borbás², László Somsák³

Affiliations

¹ Department of Organic Chemistry, PO Box 20, University of Debrecen, H-4010 Debrecen, Hungary.
² Department of Pharmaceutical Chemistry, PO Box 78, University of Debrecen, H-4010 Debrecen, Hungary.
³ Department of Organic Chemistry, PO Box 20, University of Debrecen, H-4010 Debrecen, Hungary. Electronic address: somsak.laszlo@science.unideb.hu.

PMID: 26101155
DOI: 10.1016/j.carres.2015.05.008

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.

Keywords: Disaccharide mimicks; Exo-galactal; Exo-xylal; Thiol-ene click reaction.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Biomimetic Materials / chemistry*
Galactose / chemistry*
Photochemical Processes*
Stereoisomerism
Sulfhydryl Compounds / chemistry*
Sulfides / chemistry
Xylose / chemistry*

Substances

Sulfhydryl Compounds
Sulfides
Xylose
Galactose