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Issue 20, 2020
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Efficient synthesis of a galectin inhibitor clinical candidate (TD139) using a Payne rearrangement/azidation reaction cascade

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Abstract

Selective galectin inhibitors are valuable research tools and could also be used as drug candidates. In that context, TD139, a thiodigalactoside galectin-3 inhibitor, is currently being evaluated clinically for the treatment of idiopathic pulmonary fibrosis. Herein, we describe a new strategy for the preparation of TD139. Starting from inexpensive levoglucosan, we used a rarely employed reaction cascade: Payne rearrangement/azidation process leading to 3-azido-galactopyranose. The latter intermediate was efficiently converted into TD139 in a few simple and practical steps.

Graphical abstract: Efficient synthesis of a galectin inhibitor clinical candidate (TD139) using a Payne rearrangement/azidation reaction cascade

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Supplementary files

Article information


Submitted
01 May 2020
Accepted
07 May 2020
First published
07 May 2020

Org. Biomol. Chem., 2020,18, 3903-3907
Article type
Paper

Efficient synthesis of a galectin inhibitor clinical candidate (TD139) using a Payne rearrangement/azidation reaction cascade

J. St-Gelais, V. Denavit and D. Giguère, Org. Biomol. Chem., 2020, 18, 3903
DOI: 10.1039/D0OB00910E

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