Synthesis of the branched-chain sugar aceric acid: A unique component of the pectic polysaccharide rhamnogalacturonan-II

Jones, Nigel A., Nepogodiev, Sergey A., Macdonald, Colin J., Hughes, David L. and Field, Robert A. (2005) Synthesis of the branched-chain sugar aceric acid: A unique component of the pectic polysaccharide rhamnogalacturonan-II. The Journal of Organic Chemistry, 70 (21). pp. 8556-8559. ISSN 0022-3263

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Abstract

Described herein is the synthesis of 3-C-carboxy-5-deoxy-l-xylose (aceric acid), a rare branched-chain sugar found in the complex pectic polysaccharide rhamnogalacturonan-II. The key synthetic step in the construction of aceric acid was the stereoselective addition of 2-trimethylsilyl thiazole to 5-deoxy-1,2-O-isopropylidene-α-l-erythro-pentofuran-3-ulose (2), which was prepared from l-xylose. The thiazole group was efficiently converted into the required carboxyl group via conventional transformations. Aceric acid was also synthesized by dihydroxylation of a 3-C-methylene derivative of 2 followed by oxidation of the resulting hydroxylmethyl group. The C-2 epimer of aceric acid was also synthesized using thiazole addition chemistry, starting from l-arabinose.

Item Type:	Article
Faculty \ School:	Faculty of Science > School of Chemistry
Depositing User:	Pure Connector
Date Deposited:	11 Jan 2016 12:00
Last Modified:	02 Mar 2023 10:30
URI:	https://ueaeprints.uea.ac.uk/id/eprint/56176
DOI:	10.1021/jo051012b

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