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Updated: Jul 29, 2025

Synthesis of a Thiol Building Block for the Crystallization of a Semiconducting Gyroidal Metal-sulfur Framework
Published on: April 9, 2018
New Synthesis of Diarylmethanes, Key Building Blocks for SGLT2 Inhibitors
Masahiko Seki1,2, Sandeep Ramesharao Tapkir2, Maheshwara Reddy Nadiveedhi2
1R&D Planning Department, Tokuyama Corporation, 40 Wadai, Tsukuba, Ibaraki 300-4247, Japan.
Abstract:
Synthesis of diarylmethanes, a key building block for SGLT2 inhibitors, has been developed through ketone synthesis by Friedel-Crafts acylation with TiCl4, followed by reduction with TiCl4/NaBH4. The new protocol proceeded more cleanly than the previous methods employing AlCl3 and BF3·OEt2/Et3SiH to provide the diarylmethanes corresponding to canagliflozin, empagliflozin, and luseogliflozin in a highly expedient and affordable manner. In the case of a diarylmethane for the synthesis of dapagliflozin, the reduction step took place by an alternative method using InCl3/Al/BF3·OEt2.
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