Investigations of the formation of cyclic acetal and ketal derivatives of D-ribono-1,4-lactone and 2-deoxy-D-ribono-1,4-lactone

So Yeop Han, Madeleine M. Joullié, Nicos A. Petasis, Joaquim Bigorra, Jordi Corbera, Josep Font, Rosa M. Ortuño

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28 Citations (Scopus)

Abstract

The reactions of D-ribono-1,4-lactone, and 2-deoxy-D-ribono-1,4-lactone with benzaldehyde and acetone in acidic media were investigated. The products obtained were isolated and characterized. The 1H NMR spectra of the 1,5-lactone product resulting from the thermodynamically controlled reaction of D-ribono-1,4-lactone with benzaldehyde were examined between 300 °K and 200 °K in a polar solvent. No conformational changes in the 1,5-lactone ring were observed within this temperature range. Detailed NMR studies showed that the acetalization of D-ribono-1,4-lactone proceeded with the initial formation of the endo-2,3-acetal derivative, which in the presence of aqueous acids underwent ring expansion and isomerization to the 3,4-acetal of the 1,5-lactone. The endo preference of benzylidene acetals was explained by the transition state conformation of the reactants and the thermodynamic stability of the products, as calculated with molecular mechanics. © 1993.
Original languageEnglish
Pages (from-to)349-362
JournalTetrahedron
Volume49
Issue number2
DOIs
Publication statusPublished - 8 Jan 1993

Keywords

  • 2-deoxy-D-ribono-1
  • 4-lactone
  • acetal
  • D-ribono-1
  • ketal

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