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

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.
Authors	Jacob St-Gelais, Vincent Denavit, Denis Giguère
Journal	Organic & biomolecular chemistry (Org Biomol Chem) Vol. 18 Issue 20 Pg. 3903-3907 (05 27 2020) ISSN: 1477-0539 [Electronic] England
PMID	32400847 (Publication Type: Journal Article, Research Support, Non-U.S. Gov't)
Chemical References	Blood Proteins Galectins LGALS3 protein, human Thiogalactosides Triazoles GB-0139
Topics	Blood Proteins (antagonists & inhibitors, metabolism) Carbohydrate Conformation Crystallography, X-Ray Galectins (antagonists & inhibitors, metabolism) Humans Models, Molecular Thiogalactosides (chemical synthesis, chemistry, pharmacology) Triazoles (chemical synthesis, chemistry, pharmacology)

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