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Jones, Nigel A., Nepogodiev, Sergey A., Macdonald, Colin J., Hughes, David L. and Field, Robert A. 
ORCID: https://orcid.org/0000-0001-8574-0275
(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
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 (former - to 2024) Faculty of Science > School of Chemistry, Pharmacy and Pharmacology |
| Depositing User: | Pure Connector |
| Date Deposited: | 11 Jan 2016 12:00 |
| Last Modified: | 24 Sep 2024 11:30 |
| URI: | https://ueaeprints.uea.ac.uk/id/eprint/56176 |
| DOI: | 10.1021/jo051012b |
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