292061-12-2

Upstream product

• 123-11-5 4-methoxy-benzaldehyde 
• 15100-75-1 L-phenylalanine tert-butyl ester hydrochloride 

Downstream Products

• 344765-11-3 methyl N-(4-methoxy)benzyl-N-chloroacetyl-L-phenylalaninate 
• 344765-39-5 4-benzyl-1-(p-methoxybenzyl)-4-carboxy-2-azetidinone 
• 439589-24-9 (S)-2-[Benzyloxycarbonyl-(4-methoxy-benzyl)-amino]-3-phenyl-propionic acid (1R,2S,4S)-1-[(dicyclohexylsulfamoyl)-methyl]-7,7-dimethyl-bicyclo[2.2.1]hept-2-yl ester 
• 439589-25-0 (S)-2-[Benzyloxycarbonyl-(4-methoxy-benzyl)-amino]-3-phenyl-propionic acid (1S,2R,4R)-1-[(dicyclohexylsulfamoyl)-methyl]-7,7-dimethyl-bicyclo[2.2.1]hept-2-yl ester 
• 439589-27-2 (S)-2-Benzyl-1-(4-methoxy-benzyl)-4-oxo-azetidine-2-carboxylic acid (1R,2S,4S)-1-[(dicyclohexylsulfamoyl)-methyl]-7,7-dimethyl-bicyclo[2.2.1]hept-2-yl ester 
• 439589-37-4 (R)-2-Benzyl-1-(4-methoxy-benzyl)-4-oxo-azetidine-2-carboxylic acid (1S,2R,4R)-1-[(dicyclohexylsulfamoyl)-methyl]-7,7-dimethyl-bicyclo[2.2.1]hept-2-yl ester 
• 439589-19-2 (S)-2-[(2-Chloro-acetyl)-(4-methoxy-benzyl)-amino]-3-phenyl-propionic acid (1R,2S,4S)-1-[(dicyclohexylsulfamoyl)-methyl]-7,7-dimethyl-bicyclo[2.2.1]hept-2-yl ester 
• 439589-20-5 (S)-2-[(2-Chloro-acetyl)-(4-methoxy-benzyl)-amino]-3-phenyl-propionic acid (1S,2R,4R)-1-[(dicyclohexylsulfamoyl)-methyl]-7,7-dimethyl-bicyclo[2.2.1]hept-2-yl ester 
• 439589-16-9 (S)-2-(4-Methoxy-benzylamino)-3-phenyl-propionic acid (1R,2S,4S)-1-[(dicyclohexylsulfamoyl)-methyl]-7,7-dimethyl-bicyclo[2.2.1]hept-2-yl ester 
• 439589-17-0 (S)-2-(4-Methoxy-benzylamino)-3-phenyl-propionic acid (1S,2R,4R)-1-[(dicyclohexylsulfamoyl)-methyl]-7,7-dimethyl-bicyclo[2.2.1]hept-2-yl ester 
• 439589-22-7 Cbz,PMB-Phe-OH 
• 439589-31-8 (S)-2-Benzyl-1-(4-methoxy-benzyl)-4-oxo-azetidine-2-carboxylic acid 
• 439589-35-2 (R)-2-Benzyl-1-(4-methoxy-benzyl)-4-oxo-azetidine-2-carboxylic acid 
• 113890-23-6 (S)-α-benzylaspartic acid 

Relevant academic research and scientific papers

Amino acid-derived 4-alkyl-4-carboxy-2-azetidinones. New insights into β-lactam ring formation and n-deprotection

The preparation and N-deprotection of a series of phenylalanine-derived 2-azetidinones incorporating 2,4-dimethoxybenzyl (Dmb), 2,3,4-, 2,4,6- and 3,4,5-trimethoxybenzyl (Tmb) groups at 1 position are described. The base-promoted cyclization of the corresponding methoxy-substituted Nαbenzyl-Nα-chloroacetyl derivatives to the 1,4,4-trisubstituted azetidinones proceeded with moderate to good yields, except for the 2,4,6-Tmb analogue. In spite of the number and position of the OMe groups, N-unsubstituted β-lactams were obtained by oxidative debenzylation using potassium peroxodisulfate. Alternatively, debenzylation of Pmb, Dmb and Tmb 2-azetidinones with TFA/anisole resulted in concomitant β-lactam opening to α-benzylaspartic acid derivatives.

Cell adhesion antagonists: Synthesis and evaluation of a novel series of phenylalanine based inhibitors

Several phenylalanine based inhibitors were synthesized as antagonists of the leukocyte cell adhesion process that is mediated through the interactions of the mucosal addressin cell adhesion molecule (MAdCAM) and the intgerin α4β7. Analogues 20, 21, 22 and 24 displayed inhibition of adhesion in a cell based assay in the low micromolar range. (C) 2000 Published by Elsevier Science Ltd.