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

Nigel A. Jones, Sergey A. Nepogodiev, Colin J. Macdonald, David L. Hughes, Robert A. Field

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20 Citations (Scopus)


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.
Original languageEnglish
Pages (from-to)8556-8559
Number of pages4
JournalThe Journal of Organic Chemistry
Issue number21
Publication statusPublished - 1 Oct 2005

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