Some observations on the reductive ring opening of 4,6-O-benzylidene acetals of hexopyranosides with the borane trimethylamine-aluminium chloride reagent

Katalin Daragics, Pál Szabó, Péter Fügedi

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6 Citations (Scopus)


Reductive ring openings of 3-O-benzoyl-4,6-O-benzylidene-d-glucopyranosides with BH3·NMe3-AlCl3 are accompanied by side reactions, such as debenzoylation and reduction of the benzoate to benzyl ether. This phenomenon was rationalized by aluminium chelate formation between the O-4 acetal and the benzoyl carbonyl group oxygens. It was also shown that these side reactions can be eliminated by using BH3·THF as the reducing agent.

Original languageEnglish
Pages (from-to)1633-1637
Number of pages5
JournalCarbohydrate Research
Issue number12
Publication statusPublished - Sep 6 2011



  • Benzylidene acetals
  • Borane trimethylamine-aluminium chloride
  • By-products
  • Chelation
  • Reductive ring opening

ASJC Scopus subject areas

  • Analytical Chemistry
  • Biochemistry
  • Organic Chemistry

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