25022-97-3Relevant academic research and scientific papers
Reagents and methods for esterification
-
Page/Page column 14; 20, (2020/03/18)
A method for esterification of one or more carboxylic acid groups in a compound containing one or more carboxylic acid groups wherein the esterification reagent is a diazo-compound of formula: wherein the R1 and R2 groups of the diazo compound are selected such that the corresponding organic compound of formula: exhibits a —C—H pKa value between 18 and 29 as measured in DMSO. Specific reagents and methods for esterification are provided. The esterification reagents provided exhibit high selectivity for esterification of carboxylic acid groups over reaction with amine, alcohol or thiol groups in the compound containing one or more carboxylic acid groups. The method can be used to selectively esterify carboxylic acid groups in peptides or proteins.
Diazo compounds for the bioreversible esterification of proteins
McGrath, Nicholas A.,Andersen, Kristen A.,Davis, Amy K. F.,Lomax, Jo E.,Raines, Ronald T.
, p. 752 - 755 (2015/02/18)
A diazo compound is shown to convert carboxylic acids to esters efficiently in an aqueous environment. The basicity of the diazo compound is critical: low basicity does not lead to a reaction but high basicity leads to hydrolysis. This reactivity extends to carboxylic acid groups in a protein. The ensuing esters are hydrolyzed by human cellular esterases to regenerate protein carboxyl groups. This new mode of chemical modification could enable the key advantages of prodrugs to be translated from small-molecules to proteins. This journal is
Copper-catalyzed benzylic oxidation of C(sp3)-H bonds
Zhang, Bo,Zhu, Shou-Fei,Zhou, Qi-Lin
supporting information, p. 2033 - 2037 (2013/03/13)
A selective oxidation of benzylic C(sp3)-H bonds to C(sp 3)-O bonds catalyzed by copper complexes of quinoline-imine ligands was developed with peresters as oxidants under mild reaction conditions, which converted benzylic methylenes directly into benzylic alcohols and esters by means of direct C-H bond functionalization.
Benzylic-acetoxylation of alkylbenzenes with PhI(OAc)2 in the presence of catalytic amounts of TsNH2 and I2
Baba, Haruka,Moriyama, Katsuhiko,Togo, Hideo
experimental part, p. 4303 - 4307 (2011/08/22)
Treatment of alkylbenzenes with (diacetoxyiodo)benzene in the presence of catalytic amounts of p-toluenesulfonamide or p-nitrobenzenesulfonamide, and molecular iodine in 1,2-dichloroethane at 60 °C gave the corresponding (α-acetoxy)alkylbenzenes in good to moderate yields. The present reaction is a simple method for the introduction of an acetoxy group to the benzylic position of alkylbenzenes.
