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DOI: 10.1055/a-1532-5825
An Efficient and Practical Chemoenzymatic Route to (3R,3aR,6R,6aR)-Hexahydrofuro[3,2-b]furan-6-amino-3-ol (6-Aminoisomannide) from Renewable Sources
This work was supported by the University of Pisa.
Abstract
The synthesis of 6-aminoisomannide is easily achieved starting from the renewable, inexpensive, and commercially available isosorbide in 66% overall yield. A biocatalyzed highly regioselective acetylation of the 3-endo hydroxyl group of isosorbide was followed by the stereospecific interconversion of the 6-exo hydroxyl group into an azido group, through reaction with trifluoromethanesulfonic anhydride, followed by nucleophilic displacement of the triflate group by sodium azide. Finally, reduction of the azido group and deacetylation of the 3-hydroxy group were performed in one pot using LiAlH4.
Supporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/a-1532-5825.
- Supporting Information
Publication History
Received: 01 May 2021
Accepted after revision: 27 May 2021
Accepted Manuscript online:
21 June 2021
Article published online:
06 July 2021
© 2021. The Author(s). This is an open access article published by Thieme under the terms of the Creative Commons Attribution-NonDerivative-NonCommercial-License, permitting copying and reproduction so long as the original work is given appropriate credit. Contents may not be used for commercial purposes or adapted, remixed, transformed or built upon. (https://creativecommons.org/licenses/by-nc-nd/4.0/)
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