Synthesis and photoinitiated thiol-ene reactions of exo-mannals - a new route to C-β-d-mannosyl derivatives

János József; Nóra Debreczeni; Dániel Eszenyi; Anikó Borbás; László Juhász; László Somsák

doi:10.1039/d0ra07115c

Synthesis and photoinitiated thiol-ene reactions of exo-mannals - a new route to C-β-d-mannosyl derivatives

RSC Adv. 2020 Sep 22;10(57):34825-34836. doi: 10.1039/d0ra07115c. eCollection 2020 Sep 16.

Authors

János József^{1

2}, Nóra Debreczeni^{3

2

4}, Dániel Eszenyi³, Anikó Borbás³, László Juhász¹, László Somsák¹

Affiliations

¹ Department of Organic Chemistry, University of Debrecen PO Box 400 H-4002 Debrecen Hungary juhasz.laszlo@science.unideb.hu somsak.laszlo@science.unideb.hu +36-52-512900/22464, +36-52-512900/22348.
² University of Debrecen, Doctoral School of Chemistry PO Box 400 H-4002 Debrecen Hungary.
³ Department of Pharmaceutical Chemistry, University of Debrecen PO Box 400 H-4002 Debrecen Hungary.
⁴ HAS-UD Molecular Recognition and Interaction Research Group, University of Debrecen Egyetem tér 1 Debrecen 4032 Hungary.

Abstract

Syntheses of acyl protected exo-mannal derivatives were developed starting from O-peracylated mannopyranoses via the corresponding anhydro-aldose tosylhydrazones under modified Bamford-Stevens conditions. The synthesis of analogous O-peralkylated (benzylated and isopropylenated) derivatives was carried out from pyranoid and furanoid mannonolactones using methylene transfer reagents. Photoinitiated thiol-ene additions of these exo-mannals resulted in the corresponding C-(mannopyranosyl/mannofuranosyl)methyl sulfides in medium to good yields with exclusive regio- and β(d) stereoselectivities.