257628-04-9

Upstream product

• 257628-02-7 L-N^α-benzyloxycarbonyl-4-(1,2-dihydroxyethyl)phenylalanine benzyl ester 
• 257628-09-4 L-N^α-benzyloxycarbonyl-4-(hydroxymethyl)phenylalanine benzyl ester 
• 257628-10-7 L-N^α-benzyloxycarbonyl-4-(bromomethyl)phenylalanine benzyl ester 
• 257628-01-6 L-N^α-benzyloxycarbonyl-4-[1-(2-ethenyl)]phenylalanine benzyl ester 
• 257628-03-8 L-N^α-benzyloxycarbonyl-4-(formyl)phenylalanine benzyl ester 
• 183070-41-9 L-N^α-Cbz-4-(O-trifluoromethanesulfonate)tyrosine benzyl ester 
• 166409-74-1 (4-bromomethylbenzyl)phosphonic acid di-tert-butyl ester 
• 174969-89-2 (4-methylbenzyl)phosphonic acid di-tert-butyl ester 
• 104-81-4 4-Methylbenzyl bromide 
• 13086-84-5 di-tert-butyl phosphite 
• 597564-62-0 (3S,5S,6R)-4-(benzyloxycarbonyl)-5,6-diphenyl-3-[4'-(di-tert-butylphosphonomethyl)benzyl]-2,3,5,6-tetrahydro-4H-1,4-oxazin-2-one 
• 257628-08-3 L-N^α-benzyloxycarbonyl-4-[(di-tert-butyl)phosphonomethyl]phenylalanine benzyl ester 

Downstream Products

• 166409-77-4 L-N_α-(9-fluorenylmethoxycarbonyloxy)-4-[(di-tert-butyl)phosphonomethyl]phenylalanine 
• 142434-81-9 Phosphonomethyltyrosine 

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.