Lewis-acid-catalysed isomerisation of benzylidene acetals of methyl α-l-rhamnopyranoside and methyl β-l-arabinopyranoside derivatives

János Harangi, A. Lipták, V. Anna Oláh, Pál Nánási

Research output: Contribution to journalArticle

19 Citations (Scopus)

Abstract

The Lewis-acid-catalysed isomerisation of several derivatives of methyl 2,3-O-benzylidene-α-l-rhamnopyranoside and methyl 3,4-O-benzylidene-β-l-arabinopyranoside has been investigated. The presence of equatorial substituents vicinal to the benzylidene ring decreases the rate of isomerisation, and exo isomers isomerise more quickly than the corresponding endo isomers. The occurrence of isomerisation during the reductive cleavage reaction of acetal rings with LiAlH4-AlCl3 has been demonstrated.

Original languageEnglish
Pages (from-to)165-171
Number of pages7
JournalCarbohydrate Research
Volume98
Issue number2
DOIs
Publication statusPublished - Dec 16 1981

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Lewis Acids
Acetals
Isomerization
Derivatives
Isomers
methyl rhamnopyranoside
aluminum chloride
lithium aluminum hydride

ASJC Scopus subject areas

  • Biochemistry
  • Molecular Biology
  • Organic Chemistry

Cite this

Lewis-acid-catalysed isomerisation of benzylidene acetals of methyl α-l-rhamnopyranoside and methyl β-l-arabinopyranoside derivatives. / Harangi, János; Lipták, A.; Oláh, V. Anna; Nánási, Pál.

In: Carbohydrate Research, Vol. 98, No. 2, 16.12.1981, p. 165-171.

Research output: Contribution to journalArticle

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