Synthesis of the Branched-Chain Sugar Aceric Acid:  A Unique Component of the Pectic Polysaccharide Rhamnogalacturonan-II

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-...

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Veröffentlicht in:Journal of organic chemistry 2005-10, Vol.70 (21), p.8556-8559
Hauptverfasser: Jones, Nigel A, Nepogodiev, Sergey A, MacDonald, Colin J, Hughes, David L, Field, Robert A
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Sprache:eng
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Zusammenfassung: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.
ISSN:0022-3263
1520-6904
DOI:10.1021/jo051012b