40298-69-9

Usage

Chemical Properties

Crystalline

Upstream product

• 60-18-4 L-tyrosine 
• 20443-98-5 2,6-Dichlorobenzyl bromide 

Downstream Products

• 40298-71-3 N-tert-butoxycarbonyl-O-2,6-dichlorobenzyl-L-tyrosine 
• 60-18-4 L-tyrosine 
• 306775-51-9 (S)-N^α-phthaloyl-O-(2,6-dichlorobenzyl)tyrosine 
• 1020666-11-8 (S)-3-[4-(2,6-dichlorobenzyloxy)-phenyl]-2-ureidopropionic acid 
• 306775-52-0 (S)-N^α-phthaloyl-O-2,6-dichlorobenzyltyrosinylglycine tert-butyl ester 
• 306775-54-2 3-[2(S)-(1,3-dihydro-1,3-dioxo-2H-isoindol-2-yl)-3-(4-(2,6-dichlorobenzyloxyphenyl))propanoyl]-5-oxazolidinone 
• 306775-53-1 (S)-N^α-phthaloyl-O-2,6-dichlorobenzyltyrosinylglycine 

Relevant academic research and scientific papers

Sulphonamide-based small molecule VLA-4 antagonists

The discovery of a sulphonamide by-product with VLA-4 antagonistic activity led to a series of potent, small molecule VLA-4 antagonists. Synthesis, SAR and in vivo evaluation of the selected compound will be presented.

Efficient synthesis of (S)-4-phthalimido-1,3,4,5-tetrahydro-8-(2,6-dichlorobenzyloxy)-3-oxo-2H-2-ben zazepin-2-acetic acid (Pht-Hba(2,6,Cl2-Bn)-Gly-OH)

4-Amino-2-benzazepin-3-ones have proven very useful for studying the biologically active conformations of peptides. The synthesis of Pht-Aba-Xaa-OH by reaction of the corresponding 1,3-oxazolidin-5-one with trifluoromethanesulfonic acid (TFMSA) has been reported in the literature. However, when this procedure was applied to the preparation of Pht-Hba(Bn)-Gly-OH 8, many byproducts were formed and the yield of the desired aminobenzazepinones 7 and 8 was very low. We report in this paper an efficient methodology for the synthesis of Pht-Hba(2,6-Cl2-Bn)-Gly-OH 17 starting from the commercially available tyrosine. In our procedure, the dipeptide Pht-Tyr(2,6-Cl2-Bn)-Gly-OH 15 is converted to the 1,3-oxazolidin-5-one 16 which then undergoes Friedel-Crafts cyclization in the presence of tin tetrachloride to afford the desired 4-phthalimido-1,3,4,5-tetrahydro-8-(2,6-dichlorobenzyloxy)-2-benzazepin-3-one 17 in excellent yield.

Acceleration of the N(α)-deprotection rate by the addition of m-cresol to diluted methanesulfonic acid and its application to the Z(OMe)-based solid-phase syntheses of human pancreastatin-29 and magainin 1

In solid-phase peptide synthesis, the addition of m-cresol to diluted methanesulfonic acid (MSA) in dichloromethane accelerated the deprotection rate of the acid-labile α-amino protecting group, the p-methoxybenzyloxycarbonyl (Z(OMe)) group. Further, 0.1 M MSA, 20% m-cresol/CH2Cl2 was found to be a practically useful N(α)-deprotecting reagent system, since the deprotection of the Z(OMe) group occurred selectively within 30 min at room temperature, leaving intact the other side chain protecting groups, such as benzyloxycarbonyl, benzyl ester, S-p-methoxybenzyl and N(G)-mesitylene-2-sulfonyl groups. This reagent system was applied to the Z(OMe)-based solid phase syntheses of human pancreastatin-29 and magainin 1.