Regioselective ring opening of chiral N-boc protected pyroglutamate and pyroaminoadipate ethyl esters with heteronucleophiles
作者： María Teresa Molina , Celestina del Valle , Ana María Escribano , Jesús Ezquerra , Concepción Pedregal
DOI: 10.1016/S0040-4020(01)90232-7
关键词:
摘要: Abstract Mixed diesters, ω-amide and ω-thioesters are obtained from both N-Boc ethyl pyroglutamate pyroaminoadipate under neutral or basic conditions. Under conditions, the reaction is catalyzed by KCN use of Ultrasound speeds up process. In times even shorter. cases, no transesterification α-ester was observed chirality α-amino acid preserved.
elsevier.com
sci-hub.se 参考文章(23)
Gary M. Coppola, Herbert F. Schuster, Asymmetric Synthesis: Construction of Chiral Molecules Using Amino Acids ,(1987)
Nobuo Ikota, Stereocontrolled synthesis of 1,7a-diepialexine Tetrahedron Letters. ,vol. 33, pp. 2553- 2556 ,(1992) , 10.1016/S0040-4039(00)92240-8
Jesús Ezquerra, Javier de Mendoza, Concepción Pedregal, Carmen Ramírez, Regioselective nucleophilic attack on N-BOC-pyroglutamate ethyl ester Tetrahedron Letters. ,vol. 33, pp. 5589- 5590 ,(1992) , 10.1016/S0040-4039(00)61153-X
Yung-Son Hon, Yen-Chung Chang, Ming-Li Gong, Syntheses of (2S, 4S)- and (2S, 4R)-4-substituted glutamic acid analogues for neuroexcitatory activity studies Heterocycles. ,vol. 31, pp. 191- 195 ,(1990) , 10.3987/COM-89-5216
Nobuo Ikota, Synthesis of (+)-1-Deoxynojirimycin from (S)-Pyroglutamic Acid Heterocycles. ,vol. 29, pp. 1469- 1472 ,(1989) , 10.3987/COM-89-5057
Andre Rosowsky, Ronald Forsch, Jack Uren, Michael Wick, A. Ashok Kumar, James H. Freisheim, Methotrexate analogues. 20. Replacement of glutamate by longer-chain amino diacids: effects on dihydrofolate reductase inhibition, cytotoxicity, and in vivo antitumor activity. Journal of Medicinal Chemistry. ,vol. 26, pp. 1719- 1724 ,(1983) , 10.1021/JM00366A012
Martine Pugniére, Bertrand Castro, Nicole Domergue, Aldo Previero, Enzymatic synthesis of side chain benzyl esters of L-α-amino dicarboxylic acids Tetrahedron: Asymmetry. ,vol. 3, pp. 1015- 1018 ,(1992) , 10.1016/S0957-4166(00)86032-2
Derek H.R. Barton, Yolande Hervé, Pierre Potier, Josiane Thierry, Synthesis of novel α-amino-acids and derivatives using radical chemistry: synthesis of - and -α-amino-adipic acids, -α Tetrahedron. ,vol. 43, pp. 4297- 4308 ,(1987) , 10.1016/S0040-4020(01)90305-9
Hiyoshizo Kotsuki, Mitsuhiro Iwasaki, Hitoshi Nishizawa, A new powerful method for the transformation of lactams into ω-amino-carboxamides under high pressure conditions Tetrahedron Letters. ,vol. 33, pp. 4945- 4948 ,(1992) , 10.1016/S0040-4039(00)61241-8
Amos B. Smith, Brian A. Salvatore, Kenneth G. Hull, James J.-W. Duan, Calyculin synthetic studies. 2. Stereocontrolled assembly of the C(9)-C(13) dithiane and C(26)-C(37) oxazole intermediates Tetrahedron Letters. ,vol. 32, pp. 4859- 4862 ,(1991) , 10.1016/S0040-4039(00)93480-4