124552-55-2Relevant academic research and scientific papers
Syntheses and reactivities of non-symmetrical "active ester" bi-dentate cross-linking reagents having a phthalimidoyl and acid chloride, 2-benzothiazole, or 1-benzotriazole group
Sheikh, Md. Chanmiya,Takagi, Shunsuke,Sakai, Mebumi,Mori, Tasuya,Hayashi, Naoto,Fujie, Tetsuo,Ono, Shin,Yoshimura, Toshiaki,Morita, Hiroyuki
supporting information; experimental part, p. 1244 - 1254 (2011/04/15)
We have newly synthesized the non-symmetrical "phthalimidoyl active ester" bi-dentate cross-linking reagents having an acid chloride, 2-benzothiazole, or 1-benzotriazole group (i.e., 9, 15, and 16) on the basis of the reactivity study of the "active ester" model compounds, 11-14, toward the various nucleophiles and examined their reaction selectivity towards the same nucleophiles. Then, we applied for the modification of cholesterol at the more reactive site of the bi-dentate linkers to give 3β-cholesteryl 4-(phthalimidoyloxycarbonyl)butyrate (39), and the subsequent reaction of 39 with several amines, such as benzylamine, 4-chlorobenzylamine, 2-phenylethylamine, l-phenylalanine methyl ester, or diphenylalanine benzyl ester as a protein model of the cholesterol antigen.
Mechanistic studies of DCC/HOBt-mediated reaction of 3-phenylpropionic acid with benzyl alcohol and studies on the reactivities of 'active ester' and the related derivatives with nucleophiles
Sheikh, Md. Chanmiya,Takagi, Shunsuke,Yoshimura, Toshiaki,Morita, Hiroyuki
supporting information; experimental part, p. 7272 - 7278 (2010/10/02)
Despite of the extensive study for peptide synthesis, DCC-mediated esterification is left still unclear. Therefore, DCC- and DCC/HOBt-mediated reactions of 3-phenylpropionic acid (1) with benzyl alcohol were carried out under several mechanistic considerations. Further, in order to determine the reactivities of the so-called 'active esters' compounds changing the substituents bearing carbonyl and related derivatives group for the purpose of the development of new class of non-symmetry cross-linkers, we have studied the reaction of model compounds, N-(3-phenylpropionyloxy)benzotriazole (6), N-(3-phenylpropionyloxy)phthalimide (7), 3-phenylpropionyloxybenzothiazole (8), and N-(3-phenylpropionyl)benzotriazole (9) with various nucleophiles under similar conditions were carried out for the comparison. It was revealed to exhibit the order of 6>>8>9>7.
First synthesis of non-symmetrical "phthalimidoyl active ester" bi-dentate cross-linking reagents having an acid chloride, 2-benzothiazole, or 1-benzotriazol group
Sheikh, Md. Chanmiya,Takagi, Shunsuke,Sakai, Mebumi,Abe, Hitoshi,Morita, Hiroyuki
supporting information; experimental part, p. 4505 - 4508 (2009/03/12)
For the purpose of modification of a variety of derivatives, including biologically important compounds, such as sugar derivatives and proteins etc., we have first synthesized several non-symmetrical bi-dentate cross-linking reagents, namely 3-(phthalimidoyloxycarbonyl)butyric acid chloride (1), 4-(2-benzothiazolyloxycarbonyl)butyric-N-hydroxyphthalimide ester (4) and 4-(1-benzotriazoleoxa)butyric-N-hydroxyphthalimide ester (5).
ACYL DERIVATIVES OF HYDROXAMIC ACIDS AS A SOURCE OF CARBON RADICALS
Barton, Derek H. R.,Blundell, Paul,Jaszberenyi, Joseph Cs.
, p. 2341 - 2344 (2007/10/02)
Acyl derivatives of a number of hydroxamic acids are smoothly reduced by tributyltin hydride with initiation by AIBN to give the corresponding nor-hydrocarbons in a new radical chain reaction.
