Carbohydrate components of flavonol triaosides: A convenient synthesis of O-α-l-rhamnopyranosyl-(1→3)-O-α-l-rhamnopyranosyl-(1→6)-d-Galactose and O-α-l-rhamnopyranosyl-(1→2)-O-α-l-rhamnopyranosyl-(1→6)-d-galactose

A. Lipták, Pál Nánási, András Neszmélyi, Ingrid Riess-Maurer, Hildebert Wagner

Research output: Contribution to journalArticle

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Abstract

Condensation of 1,2:3,4-di-O-isopropylidene-α-d-galactopyranose (1) with 2,4-di-O-acetyl-3-O-(2,3,4-tri-O-acetyl-α-l-rhamnopyranosyl)-α-l-rhamnopyranosyl bromide (2), followed by subsequent removal of the isopropylidene and acetyl groups from the product, afforded the first of the title trisaccharides. The reaction of 1 with 3,4-di-O-benzyl-2-O-p-nitrobenzoyl-α-l-rhamnopyranosyl bromide and deacylation of the product gave a disaccharide derivative that was treated with 2,3,4-tri-O-acetyl-α-l-rhamnopyranosyl bromide. Removal of the protecting groups from the product gave the second (15) of the title trisaccharides. The reaction of 1 with the acetobromo derivative of 2-O-α-l-rhamnopyranosyl-l-rhamnose, with subsequent removal of protecting groups from the product, also gave trisaccharide 15.

Original languageEnglish
Pages (from-to)43-52
Number of pages10
JournalCarbohydrate Research
Volume93
Issue number1
DOIs
Publication statusPublished - Jun 16 1981

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Trisaccharides
Bromides
Galactose
Carbohydrates
Derivatives
Rhamnose
Disaccharides
Condensation
3-hydroxyflavone
propylene

ASJC Scopus subject areas

  • Biochemistry
  • Molecular Biology
  • Organic Chemistry

Cite this

Carbohydrate components of flavonol triaosides : A convenient synthesis of O-α-l-rhamnopyranosyl-(1→3)-O-α-l-rhamnopyranosyl-(1→6)-d-Galactose and O-α-l-rhamnopyranosyl-(1→2)-O-α-l-rhamnopyranosyl-(1→6)-d-galactose. / Lipták, A.; Nánási, Pál; Neszmélyi, András; Riess-Maurer, Ingrid; Wagner, Hildebert.

In: Carbohydrate Research, Vol. 93, No. 1, 16.06.1981, p. 43-52.

Research output: Contribution to journalArticle

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abstract = "Condensation of 1,2:3,4-di-O-isopropylidene-α-d-galactopyranose (1) with 2,4-di-O-acetyl-3-O-(2,3,4-tri-O-acetyl-α-l-rhamnopyranosyl)-α-l-rhamnopyranosyl bromide (2), followed by subsequent removal of the isopropylidene and acetyl groups from the product, afforded the first of the title trisaccharides. The reaction of 1 with 3,4-di-O-benzyl-2-O-p-nitrobenzoyl-α-l-rhamnopyranosyl bromide and deacylation of the product gave a disaccharide derivative that was treated with 2,3,4-tri-O-acetyl-α-l-rhamnopyranosyl bromide. Removal of the protecting groups from the product gave the second (15) of the title trisaccharides. The reaction of 1 with the acetobromo derivative of 2-O-α-l-rhamnopyranosyl-l-rhamnose, with subsequent removal of protecting groups from the product, also gave trisaccharide 15.",
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