Synthesis and 13C-NMR spectroscopic investigations of rhamnobioses

András Lipták, Pál Nánási, András Neszmélyi, Hildebert Wagner

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69 Citations (Scopus)

Abstract

A convenient method has been developed for the synthesis of all mono- and di-O-benzyl ethers of methyl α-L-rhamnopyranoside applying a new stereoselective method for the hydrogenolytic ring-cleavage of benzylidene acetals. Using the prepared dibenzyl ethers as aglycones, the (1→2)-, (1→3)- and (l→4)-linked rhamnosyl-rhamnose derivatives (13-15) were synthesised. Hydrogenolysis of the latter compounds and subsequent acetylation gave the pentaacetates (16-18) of methyl dirhamnosides, which on saponification furnished the free methyl dirhamnosides (19-21). Acetolysis of 16-18 gave the corresponding dirhamnose-hexaacetates which were transformed into the three disaccharides by saponification. The structure of each product was investigated by 13C-NMR spectroscopy, and for the purpose of 13C-NMR studies the mono-O-methyl ethers of methyl α-L-rhamnopyranoside, the diacetates and di-O-benzyl ethers of the latter compounds, and, also the diacetates of methyl α-L-rhamnopyranoside were synthesised. It has been established that, for 13C-NMR investigations of oligosaccharides, the benzyl ethers of monosaccharides are more suitable model compounds than the currently used monosaccharide methyl ethers.

Original languageEnglish
Pages (from-to)1261-1268
Number of pages8
JournalTetrahedron
Volume36
Issue number9
DOIs
Publication statusPublished - 1980

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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