609366-84-9

Upstream product

• 609366-75-8 (S)-benzyl 2-phenyl-4,5-dihydrooxazole-4-carboxylate 
• 5333-86-8 ethyl benzimidate hydrochloride 
• 60022-62-0 L-serine benzyl ester hydrochloride 

Downstream Products

• 1009641-04-6 L-N_α-benzoyl-4-[(di-tert-butyl)phosphonomethyl]phenylalanine 

Relevant academic research and scientific papers

A highly efficient route to enantiomerically pure l-N-Bz-Pmp(t-Bu)2-OH and incorporation into a peptide-based protein tyrosine phosphatase inhibitor

Phosphonomethyl phenylalanine (Pmp), a nonhydrolyzable mimic of phosphotyrosine, is an important building block in the development of peptide-based PTP inhibitors. We have designed a novel, efficient synthesis of N-Bz-Pmp(t-Bu)2-OH. A Pmp-conta

Efficient synthesis of β-halogeno protected L-alanines and their β-phosphonium derivatives

Ring opening of oxazolines, prepared from L-serinates, with trimethylsilyl halides (TMSX) led to β-halogeno-N-benzoyl-α-amino esters in good to excellent yields. Quaternization of triphenylphosphine by the β-bromo or -iodo amino esters gave the corresponding β-phosphonium salts in overall yields of up to 93% and with e.e. >96%. Hydrolysis of the ester function afforded the phosphonium salt bearing an N-benzoyl-α-amino acid substituent, with partial racemization. However, the reaction of the TMSX with the carboxylic salt, prepared by saponification of the starting oxazoline ester, furnished the corresponding β-halogeno-N-benzoyl-α-amino acids in 70-95% yields. Quaternization of triphenylphosphine by the bromo or iodo derivatives led to the phosphonium salts bearing a free acid function in 95% yield, without racemization. The efficiency of this synthesis was demonstrated by the preparation of these phosphonium salts in excellent overall yields, by a one-pot procedure starting from the oxazoline.