166409-77-4

Upstream product

• 257628-04-9 L-4-((di-tert-butyl)phosphonomethyl)phenylalanine 
• 82911-69-1 N-(9H-fluoren-2-ylmethoxycarbonyloxy)succinimide 

Downstream Products

• 264131-78-4 {4-[2-(1-{2-carbamoyl-1-[3-(5-methyl-indol-1-yl)-propylcarbamoyl]-ethylcarbamoyl}-cyclohexylcarbamoyl)-2-(9H-fluoren-9-ylmethoxycarbonylamino)-ethyl]-benzyl}-phosphonic acid di-tert-butyl ester 
• 264131-81-9 N-{1-(1-{2-carbamoyl-1-[3-(5-methyl-indol-1-yl)-propylcarbamoyl]-ethylcarbamoyl}-cyclohexylcarbamoyl)-2-[4-(di-tert-butoxy-phosphorylmethyl)-phenyl]-ethyl}-oxalamic acid tert-butyl ester 
• 264131-79-5 {4-[(S)-2-Amino-2-(1-{(S)-2-carbamoyl-1-[3-(5-methyl-indol-1-yl)-propylcarbamoyl]-ethylcarbamoyl}-cyclohexylcarbamoyl)-ethyl]-benzyl}-phosphonic acid di-tert-butyl ester 
• 264131-80-8 {4-[(S)-2-Acetylamino-2-(1-{(S)-2-carbamoyl-1-[3-(5-methyl-indol-1-yl)-propylcarbamoyl]-ethylcarbamoyl}-cyclohexylcarbamoyl)-ethyl]-benzyl}-phosphonic acid di-tert-butyl ester 

Relevant academic research and scientific papers

Concise and enantioselective synthesis of Fmoc-Pmp(But) 2-OH and design of potent Pmp-containing Grb2-SH2 domain antagonists

(Matrix presented) L-Phosphonomethylphenylalanine (L-Pmp) is an important phosphatase-resistant pTyr analogue. A most concise and stereoselective approach to the synthesis of the suitably protected Fmoc-Pmp(Bu t)2-OH was developed in

Preparation of L-N(α)-Fmoc-4-[di-(tert- butyl)phosphonomethyl]phenylalanine from L-tyrosine

The unnatural amino acid analogue, 4-(phosphonomethyl)phenylalanine (Pmp, 2), has proven to be a valuable tool for studying protein-tyrosine kinase dependent signal transduction, where it is most often incorporated into peptides or peptide mimetics as a phosphatase-stable phosphotyrosyl mimetic. Although Pmp has been prepared previously bearing a number of protection strategies, the N(α)-Fmoc 4-[di-(tert-butyl)phosphonomethyl] phenylalanine form [(N(α)-Fmoc-L-Pmp((t)Bu2)-OH, 3] is particularly attractive since it can be cleanly introduced into peptides using standard Fmoc protocols. Synthesis of 3 was first reported as its (D/L)-racemate, and subsequently as its L-3 enantiomer, with the latter synthesis having relied on induction of chirality using a camphor sultam auxillary. Reported herein is an alternate enantioselective synthesis of L-3 in high enantiomeric purity by procedures which derive the stereochemistry of the final product directly from the starting amino acid, without the need for chiral induction. A key feature of the route is the racemization-free nucleophilic substitution of lithium di-tert-butyl phosphite onto protected 4-bromomethylphenylalanine (17).

Enantioselective synthesis of N-Fmoc protected di-tert-butyl 4-phosphonomethyl-L-phenylalanine: A hydrolytically stable analogue of O-phosphotyrosine

Fmoc-L-Pmp(tBu)2-OH was prepared with high enantiomeric purity by an asymmetric synthetic pathway, using a camphor sultam as chiral auxiliary.