Synthesis and 13C-NMR spectroscopic investigations of rhamnobioses

A. Lipták, Pál Nánási, András Neszmélyi, Hildebert Wagner

Research output: Contribution to journalArticle

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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

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Methyl Ethers
Ethers
Saponification
Monosaccharides
Nuclear magnetic resonance
Rhamnose
Acetylation
Acetals
Hydrogenolysis
Disaccharides
Oligosaccharides
Nuclear magnetic resonance spectroscopy
Magnetic Resonance Spectroscopy
Derivatives
methyl rhamnopyranoside
Carbon-13 Magnetic Resonance Spectroscopy

ASJC Scopus subject areas

  • Biochemistry
  • Organic Chemistry
  • Drug Discovery

Cite this

Synthesis and 13C-NMR spectroscopic investigations of rhamnobioses. / Lipták, A.; Nánási, Pál; Neszmélyi, András; Wagner, Hildebert.

In: Tetrahedron, Vol. 36, No. 9, 1980, p. 1261-1268.

Research output: Contribution to journalArticle

Lipták, A. ; Nánási, Pál ; Neszmélyi, András ; Wagner, Hildebert. / Synthesis and 13C-NMR spectroscopic investigations of rhamnobioses. In: Tetrahedron. 1980 ; Vol. 36, No. 9. pp. 1261-1268.
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