Département de Chimie, 1045 av. De la Médecine, Université Laval, GlycoNet, Québec City, Qc, Canada G1V 0A6.
Org Biomol Chem. 2020 May 27;18(20):3903-3907. doi: 10.1039/d0ob00910e.
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.
选择性半乳糖凝集素抑制剂是有价值的研究工具，也可用作药物候选物。在这种情况下，硫代二半乳糖苷半乳糖凝集素-3 抑制剂 TD139 目前正在临床上评估用于治疗特发性肺纤维化。在此，我们描述了一种制备 TD139 的新策略。从廉价的左旋葡聚糖开始，我们使用了一种很少使用的反应级联：Payne 重排/叠氮化过程导致 3-叠氮半乳糖。后者中间体通过几个简单实用的步骤有效地转化为 TD139。
