A new synthesis of C-β-d-glycopyranosylmethyl sulfides by metal-free coupling of anhydro-aldose tosylhydrazones with thiols

Tímea Kaszás, M. Tóth, L. Somsák

Research output: Contribution to journalArticle

4 Citations (Scopus)

Abstract

Herein, cross coupling reactions of O-peracylated 2,6-anhydro-aldose tosylhydrazones with aliphatic, (hetero)aromatic, and sugar-derived thiols were studied under thermal conditions in the presence of K3PO4. The reactions with aliphatic thiols provided the corresponding C-β-d-glycopyranosylmethyl sulfides in 20-50% yields, whereas the reactions with thiophenols gave the corresponding sulfides in 50-80% yields. On the other hand, sugar-derived thiols failed to yield the expected compounds with acceptable selectivity. The transformations present a new access to these types of glycomimetic compounds. The method is complementary to thiol-ene additions of exo-glycals (also obtained from the abovementioned tosylhydrazones) that provide good yields of aliphatic and sugar-derived C-glycosylmethyl sulfides. Thus, anhydro-aldose tosylhydrazones serve as a common starting material towards any kind of C-glycosylmethyl sulfide type target compounds either in a direct coupling reaction or in thiol-ene additions of exo-glycals.

Original languageEnglish
Pages (from-to)13871-13880
Number of pages10
JournalNew Journal of Chemistry
Volume41
Issue number22
DOIs
Publication statusPublished - Jan 1 2017

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Sulfides
Sulfhydryl Compounds
Metals
Sugars

ASJC Scopus subject areas

  • Catalysis
  • Chemistry(all)
  • Materials Chemistry

Cite this

A new synthesis of C-β-d-glycopyranosylmethyl sulfides by metal-free coupling of anhydro-aldose tosylhydrazones with thiols. / Kaszás, Tímea; Tóth, M.; Somsák, L.

In: New Journal of Chemistry, Vol. 41, No. 22, 01.01.2017, p. 13871-13880.

Research output: Contribution to journalArticle

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