Zinc-N-base mediated synthesis of pyranoid glycals mechanistic studies

László Somsák, Janusz Madaj, Andrzej Wiśniewski

Research output: Contribution to journalArticle

9 Citations (Scopus)

Abstract

Reactions of acetobromoglucose 1 or acetylated 1-bromo-D-galactopyranosyl cyanide 3 with zinc dust in the presence of a N-base (1-methylimidazole, 4-methylpyridine, or triethylamine, pyridine, respectively) in ethyl acetate or benzene were efficiently inhibited by 10-30 mol % of 1,4-dinitrobenzene, elemental sulfur, or carbon tetrachloride. Presence of glycosyl radicals in these reactions was also shown by trapping them with tert-dodecyl mercaptan or methyl acrylate. Based on these observations and the high yielding formation of glycal derivatives 2 and 4 of high purity a free radical chain mechanism is proposed for the transformations.

Original languageEnglish
Pages (from-to)1075-1087
Number of pages13
JournalJournal of Carbohydrate Chemistry
Volume16
Issue number7
DOIs
Publication statusPublished - Jan 1 1997

ASJC Scopus subject areas

  • Biochemistry
  • Organic Chemistry

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