Liquid-Phase Total Synthesis of Plecanatide Aided by Diphenylphosphinyloxyl Diphenyl Ketone (DDK) Derivatives

Liquid-Phase Total Synthesis of Plecanatide Aided by Diphenylphosphinyloxyl Diphenyl Ketone (DDK) Derivatives

Plecanatide is an oral guanylate cyclase-C agonist for the treatment of gastrointestinal disorders. The large-scale supply of plecanatide is restrained primarily by its industrial manufacture. Herein we developed diphenylphosphinyloxyl diphenyl ketone (DDK) derivatives as greener supports with uniqu...

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Veröffentlicht in:Organic letters 2020-05, Vol.22 (9), p.3323-3328
Hauptverfasser: Li, Haidi, Chao, Jie, Zhang, Zixin, Tian, Guang, Li, Jun, Chang, Ninghui, Qin, Chuanguang
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container_end_page 3328
container_issue 9
container_start_page 3323
container_title Organic letters
container_volume 22
creator Li, Haidi
Chao, Jie
Zhang, Zixin
Tian, Guang
Li, Jun
Chang, Ninghui
Qin, Chuanguang
description Plecanatide is an oral guanylate cyclase-C agonist for the treatment of gastrointestinal disorders. The large-scale supply of plecanatide is restrained primarily by its industrial manufacture. Herein we developed diphenylphosphinyloxyl diphenyl ketone (DDK) derivatives as greener supports with unique precipitation-inducing properties to aid the liquid-phase total synthesis of plecanatide without the use of chromatography. Plecanatide could be obtained in high yield, and the ultimately sheared DDK derivative residue could be directly recycled or regenerated for reuse.
doi_str_mv 10.1021/acs.orglett.0c00616
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title Liquid-Phase Total Synthesis of Plecanatide Aided by Diphenylphosphinyloxyl Diphenyl Ketone (DDK) Derivatives
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