30563-27-0Relevant academic research and scientific papers
Synthesis of Psychrophilin e
Ngen, Sarah T. Y.,Kaur, Harveen,Hume, Paul A.,Furkert, Daniel P.,Brimble, Margaret A.
, p. 7635 - 7643 (2016)
The first total synthesis of psychrophilin E, a potent antiproliferative cyclic tripeptide isolated from Aspergillus versicolor ZLN-60, is reported herein. Key features of the synthesis include the installation of an amide bond between the indole-nitrogen of tryptophan and an anthranilic acid residue, and a high yielding macrolactamization of the linear tripeptide to the desired macrocycle.
An efficient procedure for the esterification of nitroacetic acid :Application to the preparation of Merrifield resin-bound nitroacetate
Sylvain, Catherine,Wagner, Alain,Mioskowski, Charles
, p. 875 - 878 (1999)
Nitroacetic esters are prepared in good yield by reaction, at 0 °C, of nitroacetic acid with various alcohols in the presence of DCC. These reaction conditions were applied to the preparation of Merrifield resin-bound nitroacetate.
Transesterification of Methyl 2-Nitroacetate to Superior Esters
Corsi, Massimo,Machetti, Fabrizio,Magnolfi, Stefano
, (2020/03/19)
Methyl 2-nitroacetate and methyl acetoacetate have in common the presence of an electron-withdrawing substituent geminal to the methyl ester function but the well-known ease of thermal transesterification of methyl acetoacetate has not been found in methyl 2-nitroacetate. The latter gives uncatalysed thermal transesterification only in low yield and at a temperature higher than that of methyl acetoacetate. Comparative experiments provided further insight into the reactions; protic and Lewis acid catalysts promoted the smooth exchange of the alkanoyl groups, observing first the transesterification of methyl 2-nitroacetate with ethanol, already proved difficult to proceed. Dibutyltin(IV)oxide (DBTO) catalyst offered the spur to set up a convenient synthetic methodology from methyl 2-nitroacetate, encompassing higher molecular weight and functionalised alcohols: aliphatic, unsaturated and oxidation sensitive species were suited to react, delivering the corresponding 2-nitroacetate esters in good yields in most cases.
