174969-89-2

Upstream product

• 104-81-4 4-Methylbenzyl bromide 
• 13086-84-5 di-tert-butyl phosphite 
• 13086-84-5 di-tert-butyl phosphite 

Downstream Products

• 174969-98-3 2-(Benzhydrylidene-amino)-3-[4-(di-tert-butoxy-phosphorylmethyl)-phenyl]-propionic acid ethyl ester 
• 174969-90-5 ethyl 4-(di-tert-butylphosphonomethyl)-D,L-phenylalaninate 
• 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 
• 257628-04-9 L-4-((di-tert-butyl)phosphonomethyl)phenylalanine 
• 166409-74-1 (4-bromomethylbenzyl)phosphonic acid di-tert-butyl ester 

Relevant academic research and scientific papers

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.

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

Mild and efficient Cs2CO3-promoted synthesis of phosphonates

A mild and convenient synthesis for phosphonates using cesium carbonate (Cs2CO3), tetrabutylammonium iodide (TBAI) and DMF was developed at room temperature. Numerous dialkyl phosphites were screened using a diverse array of alkyl halides and these reaction conditions were found to be highly efficient producing various phosphonates exclusively in moderate to high yields.

New synthesis of D,L-Fmoc protected 4-phosphonomethylphenylalanine derivatives and their enzymatic resolution

A new synthesis of N-Fmoc-4-phosphonomethyl-D,L-phenylalanine protected under di-tert-butyl or dimethyl phosphonate forms (Fmoc-Pmp(OR)2), suitable for solid phase peptide synthesis is described. Resolution of these hydrolytically stable analogs of O-phosphotyrosine was tried either by fractional recrystallization of diastereoisomeric salts or by using the subtilisin Carlsberg esterase. Only the enzymatic resolution of ethyl 4-[(dimethylphosphono)methyl]-D,L-phenylalaninate succeeded. These results are discussed by comparison with the literature data. The L and D amino acids were used to prepare separately, through solid-phase peptide synthesis, followed by deprotection of dimethylphosphonate group by trimethylsilyliodide (TMSI) in acetonitrile, the L and D isomers of Glu-Asp-Val-Pmp-Glu-Asn-Leu-His-Thr, a peptide corresponding to a potentially phosphorylated site of the phosphatase PTP 1C.