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The synthesis of vitamin E sugar 1,2-orthoesters

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Abstract

In this study, 3,4,6-tri-O-acetyl-1,2-O-(1-tocopheroxyethylidene)-α-d-glucopyranose (sugar 1,2-orthoester) was synthesized with good and moderate yields in the presence of an N,N-diisopropylethylamine/tetrabutylammonium iodide system via a reaction of α-tocopherol with sugar halides. The utility of sugar α- and β-chlorides, α-bromides, and α-iodide in the synthesis of aryl (α-tocopherol, 2,2,5,7,8-pentamethylchroman-6-ol and 2,6-dimethylphenol) 1,2-orthoesters was investigated. The stereoselective formation of exo-1,2-orthoesters was confirmed using 1H and 13C NMR spectroscopy.

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Acknowledgements

We are grateful to the University of Białystok (projects nos. BST-124 and BST-127) for financial support.

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  1. Institute of Chemistry, University of Białystok, Ciołkowskiego 1K, 15-245, Białystok, Poland

    Piotr Wałejko & Aneta Baj

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  1. Piotr Wałejko
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  2. Aneta Baj
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Correspondence to Piotr Wałejko.

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Wałejko, P., Baj, A. The synthesis of vitamin E sugar 1,2-orthoesters. Monatsh Chem 150, 275–282 (2019). https://doi.org/10.1007/s00706-018-2332-6

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  • DOI: https://doi.org/10.1007/s00706-018-2332-6

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