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Synthesis and Structural Characterisation of Some Carbohydrate Steroid Hybrids

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Abstract

Glycosteroids are a wide family of natural and synthetic compounds with interesting and diverse architectures. Among synthetic types, we report the synthesis of some monocatenar carbohydrate steroid hybrids connected by a spacer. The strategy is based on the use of the carboxymethylglycosyl lactone strategy towards allyl amides and their connection to an allylated steroid using a cross-metathesis reaction. The scope of the reaction included glucose, galactose and cellobiose, on the carbohydrate side, and to dihydrocholesterol on the steroid side. A series of variously protected new monocatenar synthetic glycosteroids are described.

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Data availability

The spectroscopic data supporting the findings of this study are listed in the experimental section within the paper. Some raw data files and copies of spectra be are available from the corresponding author upon reasonable request.

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Acknowledgements

This work was supported financially by The General Directorate for Scientific Research and Technological Development (DG-RSDT), Algerian Ministry of Scientific Research, for a grant to FAR. Financial support from the Ministère de la Recherche et de l’Enseignement Supérieur et le CNRS is also gratefully acknowledged. The authors acknowledge also the support from the colleagues responsible for the analytical facilities (Centre de Spectrométrie de Masse and Centre Commun de resonance Magnétique Nucléaire) of the University Claude Bernard).

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Authors and Affiliations

  1. Faculty of Science and Technology, Univ Souk Ahras, 41000, Souk Ahras, PB 1553, Algeria

    Fahima Ali-Rachedi

  2. Laboratory of Sciences and Technology of Water and Environment LSTWE, 41000, Souk Ahras, Algeria

    Fahima Ali-Rachedi

  3. UMR 5246, Université de Lyon, UCBL, CNRS, INSA Lyon, CPE Lyon, ICBMS, Bat. Lederer, 69622, Villeurbanne Cedex, France

    Fahima Ali-Rachedi, Stéphane Chambert & Yves Queneau

  4. Department of Chemistry, The University of York, York, YO10 5DD, UK

    Stephen J. Cowling

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  1. Fahima Ali-Rachedi
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Correspondence to Fahima Ali-Rachedi or Yves Queneau.

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Ali-Rachedi, F., Cowling, S.J., Chambert, S. et al. Synthesis and Structural Characterisation of Some Carbohydrate Steroid Hybrids. Chemistry Africa 6, 2419–2428 (2023). https://doi.org/10.1007/s42250-023-00658-8

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  • DOI: https://doi.org/10.1007/s42250-023-00658-8

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