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
In: Tetrahedron, Jg. 66 (2010-09-01), S. 7272-7278
Online
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Zugriff:
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.
Titel: |
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
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Autor/in / Beteiligte Person: | Yoshimura, Toshiaki ; Takagi, Shunsuke ; Md. Chanmiya Sheikh ; Morita, Hiroyuki |
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Zeitschrift: | Tetrahedron, Jg. 66 (2010-09-01), S. 7272-7278 |
Veröffentlichung: | Elsevier BV, 2010 |
Medientyp: | unknown |
ISSN: | 0040-4020 (print) |
DOI: | 10.1016/j.tet.2010.07.011 |
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