A synthesis of a versatile intermediate leading to thienamycin analogs.

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概要

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• L-Threonine was converted to a versatile azetidinone derivative stereospecifically in 3 steps. This azetidinone was further transformed to (3<I>S</I>,4<I>R</I>)-3-[(<I>R</I>)-1-hydroxyethyl]-1-(4-methoxybenzyl)-4-[(phenylthio)-carbonylmethyl]-2-azetidinone (<I>S</I>-Phenyl thioester), a key intermediate for the synthesis of thienamycin and it's biologically active analogs. Since the thiol part of this <I>S</I>-phenyl thioester can be exchanged easily with other complex or useful thiols under mild conditions, important <I>S</I>-thioester precursors for the production of carbapenem analogs were obtained in high yield.

• 公益社団法人 日本化学会の論文

著者

• MARUYAMA Hiroshi

  Chemical Research Laboratories, Sankyo Co., Ltd.

• Maruyama Hiroshi

  Chemical Research Laboratories Sankyo Co. Ltd.

• Hiraoka Tetsuo

  Process Development Laboratories, Sankyo Co., Ltd.

• Shiozaki Masao

  Process Development Laboratories, Sankyo Co., Ltd.

• Maruyama Hiroshi

  Chemical Research Laboratories of Sankyo Company Limited

関連論文

• Short-step Synthesis of a Chiral 3-(1-Hydroxyethyl)-4-cyanoazetidin-2-one Derivative(Organic Chemistry)
• A synthesis of a versatile intermediate leading to thienamycin analogs.
• Base-induced cyclization of N-(bis(ethoxycarbonyl)methyl)-2-bromo-3-hydroxybutyramide derivatives.

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