Synthesis of S-linked N-acetylneuraminic acid derivatives via photoinduced thiol-ene and thiol-yne couplings

Magdolna Csávás, Mihály Herczeg, A. Borbás

Research output: Contribution to journalArticle

4 Citations (Scopus)

Abstract

Thio-linked mono- and bivalent mimetics of α(2→3) and α(2→6)-linked sialosides were prepared by photoinduced hydrothiolation of alkenes and alkynes with the 2-mercapto sialic acid. Thiosialylation of 6-O-allyl- or 3-O-allyl-substituted galactose derivatives has been carried out by the thiol-ene click reaction. Double thiosialylation has also been achieved via thiol-yne chemistry using propargylated galactose derivatives as the alkyne components and the peracetylated 2-mercapto sialic acid as the thiol.

Original languageEnglish
Article numberST-2013-D0075-L
Pages (from-to)719-722
Number of pages4
JournalSynlett
Volume24
Issue number6
DOIs
Publication statusPublished - 2013

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N-Acetylneuraminic Acid
Sulfhydryl Compounds
Alkynes
Derivatives
Galactose
Alkenes

Keywords

  • carbohydrates
  • N -acetylneuraminic acid
  • radical additions
  • thiol-ene/thiol-yne coupling
  • thiosialosides

ASJC Scopus subject areas

  • Organic Chemistry

Cite this

Synthesis of S-linked N-acetylneuraminic acid derivatives via photoinduced thiol-ene and thiol-yne couplings. / Csávás, Magdolna; Herczeg, Mihály; Borbás, A.

In: Synlett, Vol. 24, No. 6, ST-2013-D0075-L, 2013, p. 719-722.

Research output: Contribution to journalArticle

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