Dehydrooligopeptides. VIII. Convenient syntheses of various dehydrotyrosine derivatives protected with useful N,O-protecting groups via N-carboxy dehydrotyrosine anhydrides.

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概要

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• Various <I>N</I>-benzyloxycarbonyl (Cbz) O-protected dehydrotyrosine (<I>Δ</I>Tyr) esters have been successfully synthesized mainly via two routes, in which reactions of (diethoxyphosphinyl)glycine ester with <I>p</I>-substituted benzaldehyde were included. Subsequent hydrolyses of the esters under various alkaline conditions were carried out in order to produce corresponding Cbz-<I>Δ</I>Tyr-OH derivatives, which were further converted with thionyl chloride to give <I>N</I>-carboxy dehydrotyrosine anhydrides [<I>Δ</I>Tyr·NCA]. In addition to these topics, the transformation of <I>Δ</I>Tyr·NCA to various kinds of <I>Δ</I>Tyr derivatives and a discussion on the configurational determination of all the new compounds are presented.

• 公益社団法人 日本化学会の論文

著者

• Shin Chung-gi

  Laboratory Of Oraganic Chemistry Faculty Of Engineering Kanagawa University

• Yonezawa Yasuchika

  Laboratory Of Oraganic Chemistry Faculty Of Engineering Kanagawa University

• Nishio Hiroaki

  Laboratory of Organic Chemistry, Faculty of Technology, Kanagawa University

• Obara Takumi

  Laboratory of Organic Chemistry, Faculty of Technology, Kanagawa University

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