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†

János József,^ac Nóra Debreczeni,^bcd Dániel Eszenyi,^b Anikó Borbás,

^b László Juhász

*^a and László Somsák

*^a

Author affiliations

* Corresponding authors

^a Department of Organic Chemistry, University of Debrecen, PO Box 400, H-4002 Debrecen, Hungary
E-mail: juhasz.laszlo@science.unideb.hu, somsak.laszlo@science.unideb.hu
Tel: +36-52-512900/22464, +36-52-512900/22348

^b Department of Pharmaceutical Chemistry, University of Debrecen, PO Box 400, H-4002 Debrecen, Hungary

^c University of Debrecen, Doctoral School of Chemistry, PO Box 400, H-4002 Debrecen, Hungary

^d 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.

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DOI: https://doi.org/10.1039/D0RA07115C
Article type: Paper
Submitted: 18 Aug 2020
Accepted: 06 Sep 2020
First published: 22 Sep 2020
This article is Open Access

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RSC Adv., 2020,10, 34825-34836

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

J. József, N. Debreczeni, D. Eszenyi, A. Borbás, L. Juhász and L. Somsák, RSC Adv., 2020, 10, 34825 DOI: 10.1039/D0RA07115C

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

Abstract

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

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