Comprehensive reinvestigation of the reaction of D-aldoses with meldrum's acid yielding mainly chain extended 3,6-anhydro-2-deoxy-aldono-1,4-lactones

Peter Köll, Angelika Wernicke, József Kovács, Arne Lützen

Research output: Contribution to journalArticle

15 Citations (Scopus)

Abstract

All diastereomeric aldo-D-pentoses and -D-hexoses were reacted with Meldrum's acid (2,2-dimethyl-1,3-dioxane-4,6-dione) under basic conditions. A protocol was applied and optimized which was originally reported by J. A. Galbis Perez et al. in 1990. In every case formal substitution of the anomeric hydroxyl against a carboxy-methylene group occurred thus elongating the carbon chain of the parent aldose by a C2 fragment. Products are mainly 3,6-anhydro-2-deoxy-aldono-1,4-lactones in which the lactone rings are annulated to a furanoid system. However, D-mannose and D-lyxose also gave pyranoid 3,7-anhydro-1,4-lactones. Intermediates are unsaturated open-chain 1,4-lactones (butenolides) which in some cases could be isolated as by-products. Epimerisation at C-2 of the parent aldose occurred at least partially in most reactions. The products and their acetylated derivatives were characterized by 1H and 13C NMR spectroscopy. A proposed mechanism of this reaction is supported by additional experimental evidence.

Original languageEnglish
Pages (from-to)1019-1047
Number of pages29
JournalJournal of Carbohydrate Chemistry
Volume19
Issue number8
DOIs
Publication statusPublished - Jan 1 2000

    Fingerprint

ASJC Scopus subject areas

  • Biochemistry
  • Organic Chemistry

Cite this