3,4-Anhydro-1,2-O-isopropylidene-β-D-tagatopyranose and 4,5-anhydro- 1,2-O-isopropylidene-β-D-fructopyranose

Masoud Ataie, J. Grant Buchanan, Alan R. Edgar, Richard G. Kinsman, Maria Lyssikatou, Mary F. Mahon, Pauline M. Welsh

Research output: Contribution to journalArticle

Abstract

3,4-Anhydro-1,2-O-isopropylidene-ß-D-tagatopyranose (8) and 4,5- anhydro-1,2-O-isopropylidene-ß-D-fructopyranose (10) have been prepared by treatment of 3,5-di-O-acetyl-1,2-O-isopropylidene-4-O-toluene-p-sulfonyl-ß- D-fructopyranose with methanolic sodium methoxide. The structures of 8 and 10 were assigned by 1H and 13C NMR spectroscopy and that of 10 by X-ray crystallography; both exist in half-chair conformations. Compounds 8 and 10 interconvert in aqueous sodium hydroxide, giving a ratio of 1:2 at equilibrium. The monoacetates of 8 and 10 (5-O-acetyl-3,4-anhydro-1,2-O- isopropylidene-ß-D-tagatopyranose and 3-O-acetyl-4,5-anhydro-1,2-O- isopropylidene-ß-D-fructopyranose) undergo stereospecific epoxide ring opening in 80% acetic acid to give mainly the axial monoacetates 5-O-acetyl- 1,2-O-isopropylidene-ß-D-fructopyranose and 4-O-acetyl-1,2-O-isopropylidene- ß-D-tagatopyranose, respectively. (C) 2000 Elsevier Science Ltd.

Original languageEnglish
Pages (from-to)36-43
Number of pages8
JournalCarbohydrate Research
Volume323
Issue number1-4
DOIs
Publication statusPublished - 12 Jan 1999

Keywords

  • Anhydroketose
  • Epoxide migration
  • Stereospecific ring opening

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    Ataie, M., Buchanan, J. G., Edgar, A. R., Kinsman, R. G., Lyssikatou, M., Mahon, M. F., & Welsh, P. M. (1999). 3,4-Anhydro-1,2-O-isopropylidene-β-D-tagatopyranose and 4,5-anhydro- 1,2-O-isopropylidene-β-D-fructopyranose. Carbohydrate Research, 323(1-4), 36-43. https://doi.org/10.1016/S0008-6215(99)00272-4