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二芳基甲烷的新合成方法，SGLT2抑制剂的关键构建模块

New Synthesis of Diarylmethanes, Key Building Blocks for SGLT2 Inhibitors.

作者信息

Seki Masahiko, Tapkir Sandeep Ramesharao, Nadiveedhi Maheshwara Reddy, Mulani Shaheen Kasim, Mashima Kazushi

机构信息

R&D Planning Department, Tokuyama Corporation, 40 Wadai, Tsukuba, Ibaraki 300-4247, Japan.

Graduate School of Pharmaceutical Sciences, Osaka University, 1-6 Yamadaoka, Suita, Osaka 565-0871, Japan.

出版信息

ACS Omega. 2023 May 8;8(19):17288-17295. doi: 10.1021/acsomega.3c01972. eCollection 2023 May 16.

DOI:10.1021/acsomega.3c01972
PMID:37214716
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC10193421/
Abstract

Synthesis of diarylmethanes, a key building block for SGLT2 inhibitors, has been developed through ketone synthesis by Friedel-Crafts acylation with TiCl, followed by reduction with TiCl/NaBH. The new protocol proceeded more cleanly than the previous methods employing AlCl and BF·OEt/EtSiH 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 InCl/Al/BF·OEt.

摘要

二芳基甲烷是SGLT2抑制剂的关键结构单元，其合成方法是通过用TiCl进行傅克酰基化反应合成酮，然后用TiCl/NaBH进行还原。与之前使用AlCl和BF·OEt/EtSiH的方法相比，新方法反应更纯净，能够以高效且经济的方式提供与卡格列净、恩格列净和鲁格列净相对应的二芳基甲烷。对于用于合成达格列净的二芳基甲烷，还原步骤采用了使用InCl/Al/BF·OEt的另一种方法。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/1451/10193421/3a446332e06e/ao3c01972_0007.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/1451/10193421/85279da5966b/ao3c01972_0002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/1451/10193421/1b4436cdec4a/ao3c01972_0004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/1451/10193421/663133c8acef/ao3c01972_0003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/1451/10193421/fb362452db64/ao3c01972_0005.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/1451/10193421/e13de9a1577e/ao3c01972_0006.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/1451/10193421/3a446332e06e/ao3c01972_0007.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/1451/10193421/85279da5966b/ao3c01972_0002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/1451/10193421/1b4436cdec4a/ao3c01972_0004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/1451/10193421/663133c8acef/ao3c01972_0003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/1451/10193421/fb362452db64/ao3c01972_0005.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/1451/10193421/e13de9a1577e/ao3c01972_0006.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/1451/10193421/3a446332e06e/ao3c01972_0007.jpg

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