Stereoselective hydrogenolysis of dioxolane-type benzylidene derivatives: Synthesis of some benzyl ethers of benzyl β-d-arabinopyranoside

Research output: Contribution to journalArticle

17 Citations (Scopus)

Abstract

The following derivatives of benzyl β-d-arabinopyranoside are described: exo-3,4-O-benzylidene (2), endo-3,4-O-benzylidene (3), and the 2-benzyl ether derivatives (4 and 5) of 2 and 3. Hydrogenolysis (LiAlH4-AlCl3) of the exo-isomers (2 and 4) gave mainly 4-hydroxy-3-O-benzyl derivatives (6 and 11), whereas the endo-isomers (3 and 5) gave mainly 3-hydroxy-4-O-benzyl derivatives (7 and 12). Acid hydrolysis of 4 and 5 yielded the 2-O-benzyl derivative (10).

Original languageEnglish
Pages (from-to)69-75
Number of pages7
JournalCarbohydrate Research
Volume63
Issue numberC
DOIs
Publication statusPublished - Jun 1978

ASJC Scopus subject areas

  • Analytical Chemistry
  • Biochemistry
  • Organic Chemistry

Fingerprint Dive into the research topics of 'Stereoselective hydrogenolysis of dioxolane-type benzylidene derivatives: Synthesis of some benzyl ethers of benzyl β-d-arabinopyranoside'. Together they form a unique fingerprint.

  • Cite this