142602-48-0Relevant articles and documents
The stereoselective construction of E- and Z-Δ-Ile from E-dehydroamino acid ester: the synthesis of the phomopsin A tripeptide side chain
Yasuno, Yoko,Nishimura, Akito,Yasukawa, Yoshifumi,Karita, Yuma,Ohfune, Yasufumi,Shinada, Tetsuro
, p. 1478 - 1481 (2016)
The stereoselective synthesis of the phomopsin A tripeptide side chain was achieved by using methyl 2-(((benzyloxy)carbonyl)amino)-2-(diphenoxyphosphoryl)acetate as a common synthetic precursor for the synthesis of E-Δ-dehydroisoleucine and E-Δ-aspartate.
Diastereoselective formation of (Z)-didehydroamino acid esters
Schmidt,Griesser,Leitenberger,Lieberknecht,Mangold,Meyer,Riedl
, p. 487 - 490 (2007/10/02)
The rearrangement of (E)-didehydroamino acid derivatives to the corresponding Z-derivatives under acid or basic catalysis as well as under the influence of radicals has been investigated. The condensation of N-benzyloxycarbonyl or N-tert-butoxycarbonyl protected alkyl 2-amino-2-(dimethoxyphosphoryl)acetates with aldehydes or ketones in dichloromethane in the presence of 1,8-diazabicyclo[5.4.0]undec-7-ene furnishes (Z)-didehydroamino acid ester derivatives diastereoselectively in excellent yields and with high purity.