The regioselectivity of the reductive ring-cleavage of the acetal ring of 4,6-O-benzylidenehexopyranosides

Péter Fügedi, A. Lipták, Pál Nánási, József Szejtli

Research output: Contribution to journalArticle

43 Citations (Scopus)

Abstract

The hydrogenolytic ring-cleavage of benzyl 4,6-O-benzylidene-β-d-glucopyranoside derivatives with LiAlH4-AlCl3 was investigated in relation to the bulk of the C-3 substituents (H, OMe, OEt, OPr, OBzl). In ether-dichloromethane (2:1), 4-benzyl ethers were the major products, and the ratio of the 4- and 6-benzyl ethers was strongly dependent on the steric requirement of the C-3 substituent. Hydrogenolytic ring-cleavage with various reducing agents (AlH2Cl, AlH2Br, AlH2I, Bu21AlH, and borane) was also studied and the best selectivity was found with AlH2Br. The donor ability of the solvent has significant effects on the product ratios and the reaction rates in some reductions.

Original languageEnglish
Pages (from-to)55-67
Number of pages13
JournalCarbohydrate Research
Volume104
Issue number1
DOIs
Publication statusPublished - Jun 1 1982

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Regioselectivity
Acetals
Ethers
Boranes
Methylene Chloride
Reducing Agents
Ether
Reaction rates
Derivatives
aluminum chloride
lithium aluminum hydride
4,6-O-benzylidene-glucopyranoside

ASJC Scopus subject areas

  • Biochemistry
  • Molecular Biology
  • Organic Chemistry

Cite this

The regioselectivity of the reductive ring-cleavage of the acetal ring of 4,6-O-benzylidenehexopyranosides. / Fügedi, Péter; Lipták, A.; Nánási, Pál; Szejtli, József.

In: Carbohydrate Research, Vol. 104, No. 1, 01.06.1982, p. 55-67.

Research output: Contribution to journalArticle

Fügedi, Péter ; Lipták, A. ; Nánási, Pál ; Szejtli, József. / The regioselectivity of the reductive ring-cleavage of the acetal ring of 4,6-O-benzylidenehexopyranosides. In: Carbohydrate Research. 1982 ; Vol. 104, No. 1. pp. 55-67.
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