Research article summary (published 28 Aug 2001):

Cleavage of the C-C linkage between the sugar and the aglycon in C-glycosylphloroacetophenone, and the NMR spectral characteristics of the resulting di-C-glycosyl compound.

Full Abstract

The treatment of unprotected mono-C-beta-D-glucopyranosylphloroacetophenone with a cation-exchange resin in anhydrous acetonitrile afforded both a phloroacetophenone and a di-C-beta-D-glucopyranosylphloroacetophenone. Treatment of an unprotected mono-C-(2-deoxy-beta-D-arabino-hexopyranosyl)phloroacetophenone (mono-C-2-deoxy-beta-D-glucopyranosylphloroacetophenone) also afforded both the aglycon and di-C-(2-deoxy-beta-D-arabino-hexopyranosyl)phloroacetophenone. The reaction mixtures were acetylated, and the structures of the isolated products were determined by NMR spectroscopy. This is the first demonstration of the formation of a di-C-glycosyl compound during the chemical cleavage of the C-C linkage between the sugar and the aglycon in an aryl C-glycosyl derivative.

Author information

Author/s: Kumazawa, T (T); Kimura, T (T); Matsuba, S (S); Sato, S (S); Onodera, J (J);

Affiliation: Department of Chemistry and Chemical Engineering, Faculty of Engineering, Yamagata University, 4-3-16 Jonan, Yonezawa, Yamagata 992-8510, Japan. tk111(-atsign-)dip.yz.yamagata-u.ac.jp

Journal and publication information

Publication Type: Journal Article

Journal: Carbohydrate research (Carbohydr Res), published in Netherlands. (Language: eng)

Reference: 2001-Aug; vol 334 (issue 3) : pp 207-13

Dates: Created 2001/08/21; Completed 2001/12/04;

PMID: 11513827, status: MEDLINE (last retrieval date: 2/18/2009, IMS Date: )

Sourced from the National Library of Medicine. Abstract text and other information may be subject to copyright.

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MeSH headings (categories)

This article was linked to the MESH Headings shown below.

Acetophenones - chemistry Carbon - chemistry Glycosides - chemistry

Glycosides - chemistry Magnetic Resonance Spectroscopy Molecular Structure

Associated Chemicals: Acetophenones (0) ; Glycosides (0) ; Carbon (7440-44-0)

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