Reactions of phenyl and ethyl 2-O-sulfonyl-1-thio-α-d-manno- and β-d-glucopyranosides with thionucleophiles

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Abstract

Persubstituted derivatives of phenyl and ethyl 2-O-sulfonyl-1-thio-α-d-manno- and β-d-glucopyranosides were synthesized and reacted either with PhSNa or with MeSNa. The phenyl-1-thio compounds afforded the dithio-1,2-cis-axial/equatorial-α-d-glucopyranosides or dithio-1,2-cis-equatorial/axial-β-d-mannopyranosides by means of SN2 type of reactions. Starting from the ethyl-1-thio derivatives intramolecular 1,2-thio-migration took place predominantly. In the case of mannosides both nucleophilic reagents facilitate the formation of 1-SPh- or 1-SEt glycals by elimination. The formation of unsubstituted glycal could also be observed from the ethyl-1-thio derivatives, especially by using PhSNa as a nucleophile. The 1,2-dithio-glycosides are glycosyl donors affording 1,2-trans-2-thio-glycosides.

Original languageEnglish
Pages (from-to)2461-2467
Number of pages7
JournalCarbohydrate Research
Volume344
Issue number18
DOIs
Publication statusPublished - Dec 14 2009

Keywords

  • 1,2-Thiomigration
  • 1-Substituted and unsubstituted glycals
  • Nucleophilic substitution of thioglycosides
  • Thionucleophiles

ASJC Scopus subject areas

  • Analytical Chemistry
  • Biochemistry
  • Organic Chemistry

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