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Synthesis of the disaccharides methyl 4-O-(2′/3′-O-sulfo-β-d-glucopyranosyluronic acid)-2-amino-2-deoxy-α-d-glucopyranoside disodium salts, related to heparin biosynthesis

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Abstract

The synthesis of the disaccharides methyl 4-O-(2′/3′-O-sulfo-β-d-glucopyranosyluronic acid)-2-amino-2-deoxy-α-d-glucopyranoside3 and4 as, disodium salts is described. Allyl 4,6-O-benzylidene-α-d-glucopyranoside6 was converted to trichloroacetimidate20 Glycosylation of20 with5 promoted by BF3·OEt2 gave disaccharide21. Deacetylation of21 followed by monoacetylation of the resultant diol22 afforded the two monoacetylated disaccharides23 and24. Sulfation and deprotection of each disaccharide gave the desired sulfated compounds3 and4.

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Authors and Affiliations

  1. Dipartimento di Chimica Organica e Industriale, Centro per lo Studio delle Sostanze Organiche Naturali del CNR, Università di Milano, Via Venezian 21, I-20133, Milano, Italy

    Laura Cipolla, Francesco Nicotra, Luigi Lay, Luigi Panza & Giovanni Russo

  2. Department of Medical and Physiological Chemistry, University of Uppsala, The Biomedical Centre, Box 575, S-751 23, Uppsala, Sweden

    Ulf Lindahl

Authors
  1. Laura Cipolla
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  2. Francesco Nicotra
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  3. Luigi Lay
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  4. Ulf Lindahl
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  5. Luigi Panza
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  6. Giovanni Russo
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Cipolla, L., Nicotra, F., Lay, L. et al. Synthesis of the disaccharides methyl 4-O-(2′/3′-O-sulfo-β-d-glucopyranosyluronic acid)-2-amino-2-deoxy-α-d-glucopyranoside disodium salts, related to heparin biosynthesis. Glycoconjugate J 13, 995–1003 (1996). https://doi.org/10.1007/BF01053195

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  • DOI: https://doi.org/10.1007/BF01053195

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