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Selection of protecting groups and synthesis of a β-1,4-GlcNAc-β-1,4-GlcN unit

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Abstract

The synthesis of the disaccharide tert-butyldimethylsilyl (4-O-acetyl-2-azido-3,6-di-O-benzyl-2-deoxy-β-d-glucopyranosyl)-3,6-di-O-benzyl-2-deoxy-2-phthalimido-β-d-glucopyranoside, designed as a repeating unit appearing in oligo- and polysaccharides, which exhibits a distinguished “obverse–reverse” property in β-1,4-glucan chain, was accomplished. This disaccharide was synthesized by glycosylation of a phthalimido sugar with an azido sugar. A selective removal of the two different protecting groups at C-2 for obtaining 2-acetamido-4-O-(2-amino-2-deoxy-β-d-glucopyranosyl)-2-deoxy-β-d-glucopyranose indicates that the selection and combination, using phthalimido and azido as protecting groups, are an excellent strategy for synthesizing such target disaccharides.

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Acknowledgments

This research was conducted with the support of a Grant-in-Aid for Scientific Research (18658133) from the Japan Society for the Promotion of Science (JSPS).

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Authors and Affiliations

  1. Graduate School of Life and Environmental Sciences, Kyoto Prefectural University, Shimogamo, Sakyo-ku, Kyoto, 606-8522, Japan

    Toshinari Kawada & Yuko Yoneda

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  1. Toshinari Kawada
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  2. Yuko Yoneda
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Correspondence to Toshinari Kawada.

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Kawada, T., Yoneda, Y. Selection of protecting groups and synthesis of a β-1,4-GlcNAc-β-1,4-GlcN unit. Monatsh Chem 140, 1245–1250 (2009). https://doi.org/10.1007/s00706-009-0172-0

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  • DOI: https://doi.org/10.1007/s00706-009-0172-0

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