Successful combination of (methoxydimethyl)methyl (MIP) and (2-naphthyl)methyl (NAP) ethers for the synthesis of arabinogalactan-type oligosaccharides

Magdolna Csávás, A. Borbás, László Szilágyi, A. Lipták

Research output: Contribution to journalArticle

24 Citations (Scopus)

Abstract

In order to characterise the presumed epitopes of arabinogalactans, isolated from the extract of the cell-cultured Echinacea purpurea, two oligosaccharides were synthesized. The whole synthetic route was based on the successful combination of the (methoxydimethyl)methyl (MIP) and the (2-naphthyl)methyl ether (NAP) protecting groups. A β-(1→6)-linked trigalactoside was prepared, which contained a NAP ether at position 2′.This protecting group was selectively removed using either DDQ or Pd-C/H2 and the acceptor was ready for further glycosylation. We have used two arabinofuranosyl donor compounds: 2,3,5-tri-O-acetyl arabinofuranosyl trichloroacetimidate and a peracetylated α-(1→5)-linked diarabinofuranosyl trichloroacetimidate. For the deprotection of the tetra- and pentasaccharides a common procedure was used. All of the synthesized compounds were characterized by 1H and 13C NMR spectroscopy, as well as by MALDI-TOF mass-spectrometry.

Original languageEnglish
Pages (from-to)887-890
Number of pages4
JournalSynlett
Issue number6
Publication statusPublished - 2002

Fingerprint

Methyl Ethers
Oligosaccharides
Glycosylation
Nuclear magnetic resonance spectroscopy
Mass spectrometry
Epitopes
trichloroacetamide
arabinogalactan

Keywords

  • (2-naphthyl)methyl ether (NAP)
  • (methoxydimethyl)methyl ether (MIP)
  • Arabinogalactan
  • Oligosaccharides
  • Protecting groups

ASJC Scopus subject areas

  • Organic Chemistry

Cite this

Successful combination of (methoxydimethyl)methyl (MIP) and (2-naphthyl)methyl (NAP) ethers for the synthesis of arabinogalactan-type oligosaccharides. / Csávás, Magdolna; Borbás, A.; Szilágyi, László; Lipták, A.

In: Synlett, No. 6, 2002, p. 887-890.

Research output: Contribution to journalArticle

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