213208-73-2

Upstream product

• 34893-92-0 3,4-dichlorophenyl isocyanate 
• 213202-55-2 (R)-2-amino-2-methyl-3-(4-bromophenyl)propionic acid ethyl ester 
• 91292-74-9 alanine ethyl ester-p-chlorobenzyl shiff base 
• 589-15-1 1-bromomethyl-4-bromobenzene 
• 872104-08-0 tert-butyl (R)-2-amino-3-(p-bromophenyl)-2-methylpropanoate 
• 346578-01-6 (2S,4R)-2-Biphenyl-4-yl-4-(4-bromo-benzyl)-4-methyl-5-oxo-oxazolidine-3-carboxylic acid isobutyl ester 
• 909907-87-5 (3R,6S)-3-(4-bromobenzyl)-6-isopropyl-5-methoxy-3-methyl-3,6-dihydro-2-pyrazinyl methyl ether 
• 330455-47-5 N-[(1E)-(4-bromophenyl)methylene]-1,1-diphenylmethanamine 
• 1122-91-4 4-bromo-benzaldehyde 
• 870718-66-4 (2R,3R)-1-Benzhydryl-3-(4-bromo-phenyl)-2-methyl-aziridine-2-carboxylic acid ethyl ester 
• 321901-73-9 (R)-α-methyl-4-bromophenylalanine methyl ester 
• 626-43-7 3,5-Dichloroaniline 
• 346578-03-8 (R)-3-(4-bromophenyl)-2-isobutoxycarbonylamino-2-methylpropionic acid methyl ester 
• 79-22-1 methyl chloroformate 

Downstream Products

• 213209-43-9 (R)-1-acetyl-5-(4-bromobenzyl)-3-(3,5-dichlorophenyl)-5-methylimidazolidine-2,4-dione 

Relevant academic research and scientific papers

Stereodivergent synthesis of the LFA-1 antagonist BIRT-377 by porcine liver esterase desymmetrization and Curtius rearrangement

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

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

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

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

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

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

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

(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

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

Crystallization-induced asymmetric transformations and self-regeneration of stereocenters (SROSC): Enantiospecific synthesis of α-benzylalanine and hydantoin BIRT-377

N-Isobutoxycarbonyl protected L-alanine was condensed with 4-phenylbenzaldehyde in a crystallization-controlled process to give the corresponding cis-oxazolidinone derivative as the sole product in high yield; this underwent enolization and benzylation wi