Synthesis of 2-O-α-, 3-O-α-, 3-O-β-, and 4-O-α-l-rhamnopyranosyl-d-galactose

András Lipták, Zoltán Szurmai, Pál Nánási, András Neszmélyi

Research output: Contribution to journalArticle

26 Citations (Scopus)

Abstract

Condensation of benzyl 3-O-benzoyl-4,6-O-benzylidene-, benzyl 2-O-benzoyl-4,6-O-benzylidene- (2), and benzyl2,3,6-tri-O-benzyl-{amalgamation}-d-galactopyranoside, separately, with tri-O-acetyl-α-l-rhamnopyranosyl bromide gave mainly α-linked disaccharide derivatives. An appreciable proportion of the {amalgamation}-linked disaccharide was also obtained from 2. An anomalous deacylation reaction was found for the (1→3)-linked disaccharide, and the partially benzoylated products were isolated and characterised. The anomeric configuration of each disaccharide was established on the basis of JC-1,H-1 values. The chemical shifts for the galactose moieties of the α- and β-l-rhamnopyranosyl derivatives differed in a systematic way.

Original languageEnglish
Pages (from-to)13-21
Number of pages9
JournalCarbohydrate Research
Volume99
Issue number1
DOIs
Publication statusPublished - Jan 1 1982

ASJC Scopus subject areas

  • Analytical Chemistry
  • Biochemistry
  • Organic Chemistry

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