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Synthesis 2024; 56(06): 944-952
DOI: 10.1055/a-2126-0815
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Emerging Trends in Glycoscience

Site-Selective Lewis Acid Mediated Transformation of Pseudo Glycals to 1-Deoxy-2-thioaryl/alkyl Glycosides

Bindu Tiwari
,
Manish K. Sharma
,
Ram P. Pandey
,
Nazar Hussain  ∗
Funding support was provided by IoE-BHU in the form of a seed grant and DST-SERB (EEQ/2021/000553).
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Abstract

A site-selective Lewis acid mediated transformation of pseudoglycals with various thiols for the synthesis of C-2 thioaryl glycosides was developed. The substrate scope of the reaction was explored with various thiols having various functional groups on aromatic rings as well as with pseudoglycals obtained from different sugars. The compatibility and survival of various protecting groups on pseudoglycals and substituted thiols show tolerance under the reaction conditions. Finally, the potential synthetic utility of the synthesized compounds was demonstrated and also the late-stage modifications of various drugs and pharmaceuticals were also explored.

Key words

glycals - thioglycosides - Lewis acid - transformations - pharmaceuticals

Supporting Information

    Supporting information for this article is available online at https://doi.org/10.1055/a-2126-0815.
  • Supporting Information


Publikationsverlauf

Eingereicht: 23. Mai 2023

Angenommen nach Revision: 10. Juli 2023

Accepted Manuscript online:
10. Juli 2023

Artikel online veröffentlicht:
30. August 2023

© 2023. Thieme. All rights reserved

Georg Thieme Verlag KG
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