213208-73-2Relevant academic research and scientific papers
Stereodivergent synthesis of the LFA-1 antagonist BIRT-377 by porcine liver esterase desymmetrization and Curtius rearrangement
Johnson, Aaron,Saunders, Matthew J.,Back, Thomas G.
, p. 1463 - 1469 (2015)
The LFA-1 inhibitor and leukocyte adhesion suppressor BIRT-377 was prepared in high enantiomeric excess by desymmetrization of dimethyl 2-p-bromobenzyl-2-methylmalonate, followed by condensation of the resulting carboxylic acid with 3,5-dichloroaniline, s
Application of asymmetric alkylation of malonic diester with phase-transfer catalysis: Synthesis of LFA-1 antagonist BIRT-377
Kanemitsu, Takuya,Furukoshi, Saeka,Miyazaki, Michiko,Nagata, Kazuhiro,Itoh, Takashi
, p. 214 - 218 (2015)
An efficient asymmetric synthesis of LFA-1 antagonist BIRT-377 using enantioselective phase-transfer catalytic alkylation has been developed. The alkylation of α-monosubstituted tert-butyl methyl malonate was catalyzed by a quaternary ammonium salt derived from a cinchona alkaloid to obtain the product with a quaternary stereogenic carbon in high yield and with high enantioselectivity. The chiral α,α-disubstituted product thus obtained was transformed into BIRT-377 through alternating chemoselective deprotection of the two ester groups followed by Curtius rearrangement.
Synthesis of potent lymphocyte function-associated antigen-1 inhibitors labeled with carbon-14 and deuterium, part 1
Latli, Bachir,Byrne, Denis,Nummy, Larry,Krishnamurthy, Dhileepkumar,Senanayake, Chris H.
experimental part, p. 763 - 768 (2012/02/02)
The lymphocyte function-associated antigen-1 (LFA-1) is an essential component in normal immune system function and is a target for drug discovery for its broad therapeutic potential in treating inflammatory diseases. Here, we report the synthesis of thre
Convenient preparation of chiral phase-transfer catalysts with conformationally fixed biphenyl core for catalytic asymmetric synthesis of α-alkyl- and α,α-dialkyl-α-amino acids: application to the short asymmetric synthesis of BIRT-377
Wang, Yong-Gang,Ueda, Mitsuhiro,Wang, Xisheng,Han, Zhenfu,Maruoka, Keiji
, p. 6042 - 6050 (2008/02/08)
Chiral phase-transfer catalysts (S)-1a, (S)-1b, and (S)-2 with conformationally fixed biphenyl cores were conveniently prepared from the known, easily available (S)-6,6′-dimethylbiphenyl-2,2′-diol 3 and (S)-4,5,6,4′,5′,6′-hexamethoxybiphenyl-2,2′-dicarbox
Improved Schoellkopf construction of quaternary α-amino acids: efficient enantioselective synthesis of integrin LFA-1 antagonist BIRT-377
Vassiliou, Stamatia,Magriotis, Plato A.
, p. 1754 - 1757 (2007/10/03)
The Schoellkopf methodology for the asymmetric synthesis of α-amino acids which was previously not applicable to the construction of α,α-dialkylated (quaternary) α-amino acids, has been rendered practical for this purpose and applied in a highly efficient
Highly diastereoselective alkylation of aziridine-2-carboxylate esters: Enantioselective synthesis of LFA-1 antagonist BIRT-377
Patwardhan, Aniruddha P.,Pulgam, V. Reddy,Zhang, Yu,Wulff, William D.
, p. 6169 - 6172 (2007/10/03)
The benzhydryl group is the key: Efficient alkylation of 3-substituted aziridine-2-carboxylates is only possible with N-benzhydryl-protected aziridines and occurs with complete retention of the configuration at the 2-position. Sequential catalytic asymmet
Convenient preparation of highly active phase-transfer catalyst for catalytic asymmetric synthesis of α-alkyl- and α,α-dialkyl- α-amino acids: Application to the short asymmetric synthesis of BIRT-377
Han, Zhenfu,Yamaguchi, Yukako,Kitamura, Masanori,Maruoka, Keiji
, p. 8555 - 8558 (2007/10/03)
A highly active phase-transfer catalyst was conveniently prepared from the known, easily available (S)-4,5,6,4′,5′,6′- hexamethoxybiphenyldicarboxylic acid. This catalyst exhibited the high catalytic performance (0.01-1 mol %) in the asymmetric alkylation
Total synthesis of LFA-1 antagonist BIRT-377 via organocatalytic asymmetric construction of a quaternary stereocenter
Chowdari, Naidu S.,Barbas III, Carlos F.
, p. 867 - 870 (2007/10/03)
(Chemical Equation Presented) A catalytic route for enantioselective total synthesis of cell adhesion inhibitor BIRT-377 is described. The quaternary stereocenter was constructed through L-proline-derived, tetrazole-catalyzed direct asymmetric α-amination
Practical synthesis of a cell adhesion inhibitor by self-regeneration of stereocenters
Yee, Nathan K.,Nummy, Laurence J.,Frutos, Rogelio P.,Song, Jinhua J.,Napolitano, Elio,Byrne, Denis P.,Jones, Paul-James,Farina, Vittorio
, p. 3495 - 3501 (2007/10/03)
An efficient enantiospecific synthesis of the cell adhesion inhibitor BIRT-377 by self-regeneration of stereocenters has been achieved in 38% overall yield in eight steps. The key transformations involve the stereoselective formation of the trans imidazol
