Development of a Scalable Synthesis of Tofogliflozin
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- 作者：Yoshihito Ohtake ; Takashi Emura ; Masahiro Nishimoto ; Koji Takano ; Keisuke Yamamoto ; Satoshi Tsuchiya ; Sang-Yong Yeu ; Yasushi Kito ; Nobuaki Kimura ; Sunao Takeda ; Masao Tsukazaki ; Masatoshi Murakata ; Tsutomu Sato
- 刊名：Journal of Organic Chemistry
- 出版年：2016
- 出版时间：March 4, 2016
- 年：2016
- 卷：81
- 期：5
- 页码：2148-2153
- 全文大小：325K
- ISSN：1520-6904
文摘
An efficient and scalable synthesis of an antidiabetic drug, tofogliflozin (1), which was identified as a highly selective sodium glucose cotransporter 2 (SGLT2) inhibitor, is described. A key factor in the synthesis of 1 was the selection of the purpose-designed protecting group, which plays a strategic role in protection, chemoselective activation, and crystalline purification. The developed and optimized method made it possible to prepare 1 on a multidecagram scale without any column chromatography.