Unprecedented β-manno type thiodisaccharides with a C-glycosylic function by photoinitiated hydrothiolation of 1-C-substituted glycals

László Lázár, László Juhász, G. Batta, Anikó Borbás, László Somsák

Research output: Contribution to journalArticle

9 Citations (Scopus)

Abstract

Free-radical hydrothiolation of O-peracylated 1-C-(carbamoyl-, methoxycarbonyl- and cyano) substituted glycals with a range of sugar derived thiols gave the corresponding β-manno type 3-deoxy-3-S-disaccharides with full regio- and stereoselectivity. The configuration of the glycals (arabino vs. lyxo) and the size of the protecting groups had no significant effect on the outcome of the transformations. Formation of by-products was tracked down by LCMS studies and correlated with the electron density of the double bonds to show that the reactions were synthetically useful with a COOMe and especially with a CONH2 group as the 1-C-substituent.

Original languageEnglish
Pages (from-to)1284-1292
Number of pages9
JournalNew Journal of Chemistry
Volume41
Issue number3
DOIs
Publication statusPublished - 2017

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Stereoselectivity
Regioselectivity
Disaccharides
Free radicals
Sulfhydryl Compounds
Sugars
Free Radicals
Carrier concentration
Byproducts

ASJC Scopus subject areas

  • Catalysis
  • Chemistry(all)
  • Materials Chemistry

Cite this

Unprecedented β-manno type thiodisaccharides with a C-glycosylic function by photoinitiated hydrothiolation of 1-C-substituted glycals. / Lázár, László; Juhász, László; Batta, G.; Borbás, Anikó; Somsák, László.

In: New Journal of Chemistry, Vol. 41, No. 3, 2017, p. 1284-1292.

Research output: Contribution to journalArticle

Lázár, László ; Juhász, László ; Batta, G. ; Borbás, Anikó ; Somsák, László. / Unprecedented β-manno type thiodisaccharides with a C-glycosylic function by photoinitiated hydrothiolation of 1-C-substituted glycals. In: New Journal of Chemistry. 2017 ; Vol. 41, No. 3. pp. 1284-1292.
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