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The synthesis of vitamin E sugar 1,2-orthoesters

  • Piotr WałejkoEmail author
  • Aneta Baj
Original Paper
  • 15 Downloads

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.

Graphical abstract

Keywords

α-Tocopherol Glycosides Carbohydrates Heterocycles Glycoconjugates 

Notes

Acknowledgements

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

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Copyright information

© Springer-Verlag GmbH Austria, part of Springer Nature 2019

Authors and Affiliations

  1. 1.Institute of ChemistryUniversity of BiałystokBiałystokPoland

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