Bulletin of the Chemical Society of Japan p. 3265 - 3272 (1988)
Update date:2022-08-04
Topics:
Shin, Chung-gi
Obara, Takumi
Morita, Shigeru
Yonezawa, Yasuchika
Various kinds of N-benzyloxycarbonyl (E)- and (Z)-dehydroaspartic acid (Cbz-ΔAsp) derivatives were succesfully 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-(N-Cbz)-aminomaleic acid anhydride.Moreover, for high-yield synthesis of Δ1,2-dehydrodipeptides (DHP) containing a ΔAsp residue, a similar β-elimination was applied to Δ1-DHP with C-terminal HyAsp residue.The configuration of all the new ΔAsp derivatives and their Δ1,2-DHPs were confirmed mainly on the basis of 1H NMR spectral data.
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