Dehydrooligopeptides. X. Useful synthetic method for (E)- and (Z)-isomers of dehydroaspartic acids, and their .DELTA.1,2-dehydrodipeptides by the base-catalyzed .BETA.-elimination.

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概要

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• Various kinds of <I>N</I>-benzyloxycarbonyl (<I>E</I>)- and (<I>Z</I>)-dehydroaspartic acid (Cbz–<I>Δ</I>Asp) derivatives were successfully synthesized by both a base-catalyzed β-elimination of β-hydroxyaspartic acid esters (HyAsp) via their β-mesyloxy Asp derivatives and several modes of the cleavages of α-(<I>N</I>-Cbz)-aminomaleic acid anhydride. Moreover, for high-yield synthesis of <I>Δ</I><SUP>1,2</SUP>-dehydrodipeptides (DHP) containing a <I>Δ</I>Asp residue, a similar β-elimination was applied to <I>Δ</I><SUP>1</SUP>-DHP with a C-terminal HyAsp residue. The configuration of all the new <I>Δ</I>Asp derivatives and their <I>Δ</I><SUP>1,2</SUP>-DHPs were confirmed mainly on the basis of <SUP>1</SUP>H NMR spectral data.

• 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

• Obara Takumi

  Laboratory of Organic Chemistry, Faculty of Technology, Kanagawa University

• Morita Shigeru

  Laboratory of Organic Chemistry, Faculty of Technology, Kanagawa University

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