150618-05-6

Upstream product

• 150618-03-4 N^α-Boc 4--L-phenylalanine benzyl ester 
• 150618-09-0 (S)-2-tert-Butoxycarbonylamino-3-[4-(diethoxy-phosphoranecarbonyl)-phenyl]-propionic acid benzyl ester 
• 2766-43-0 N-tert-butyloxycarbonyl-L-serine methyl ester 
• 1711-02-0 4-iodobenzoic acid chloride 
• 156017-41-3 [Difluoro-(4-iodo-phenyl)-methyl]-phosphonic acid diethyl ester 
• 156017-40-2 diethyl (4-iodobenzoyl)phosphonate 
• 113850-76-3 N-(tert-butoxycarbonyl)-4-iodo-L-phenylalanine methyl ester 
• 103882-09-3 N-Boc-4-I-Phe-OH 
• 213127-93-6 (2S)-2-{[(benzyloxy)carbonyl]amino}-3-{4-[(diethoxyphosphoryl)(difluoro)methyl]phenyl}propyl acetate 
• 213127-95-8 (2S)-2-[(tert-butoxycarbonyl)amino]-3-{4-[(diethoxyphosphoryl)(difluoro)methyl]phenyl}propyl acetate 
• 213127-91-4 (2S)-3-acetoxy-2-{4-[(diethoxyphosphoryl)(difluoro)methyl]benzyl}propanoic acid 
• 213127-82-3 (2R)-2-{4-[(diethoxyphosphoryl)(difluoro)methyl]benzyl}propyl acetate 
• 213127-68-5 dimethyl 2-{4-[(diethoxyphosphoryl)(difluoro)methyl]benzyl}malonate 
• 213127-72-1 diethyl difluoro{4-[3-hydroxy-2-(hydroxymethyl)propyl]phenyl}methylphosphonate 

Downstream Products

• 1609462-44-3 (S)-allyl 2-{(tert-butoxycarbonyl)amino}-3-[4-{(diethoxyphosphoryl)difluoromethyl}phenyl]propanoate 
• 1609462-55-6 (2S)-2-([{(9H-fluoren-9-yl) methoxy}carbonyl]amino)3-{4-(difluoro[hydroxy{(2-nitro-benzyl)oxy}phosphoryl] methyl)-phenyl}propanoic acid 
• 1609462-52-3 (2S)-allyl 2-([{(9H-fluoren-9-yl)methoxy}carbonyl]amino)-3-{4-(difluoro[hydroxy{(2-nitrobenzyl)oxy}phosphoryl]methyl)phenyl}propanoate 
• 1609462-49-8 (S)-([4-{2-([{(9H-fluoren-9-yl)methoxy}carbonyl]amino)-3-(allyloxy)-3-oxopropyl}phenyl]difluoromethyl)phosphonic acid 
• 1609462-46-5 (S)-allyl 2-([{(9H-fluoren-9-yl)methoxy}carbonyl]amino)-3-[4-{(diethoxyphosphoryl)difluoromethyl}phenyl]propanoate 

Relevant academic research and scientific papers

Enzymatic desymmetrization of prochiral 2-benzyl-1,3-propanediol derivatives: A practical chemoenzymatic synthesis of novel phosphorylated tyrosine analogues

(Phosphonomethyl)phenylalanine (Pmp) and (phosphonodifluoromethyl)phenylalanine (F2Pmp) as well as their β-amino acid congeners were prepared as a protecting variant amenable to the peptide synthesis from readily available 2-benzyl-1,3-propandiols possessing either a diethylphosphonomethyl- or diethylphosphonodifluoromethyl functionality at the para-position via the lipase-catalyzed desymmetrization.

A facile solution and solid phase synthesis of phosphotyrosine mimetic L-4-[diethylphosphono(difluoromethyl)]-phenylalanine (F2Pmp(EtO)2) derivatives

The F2Pmp derivatives were prepared in 80-90% yield from commercially available protected L-4-iodophenylalanine by esterification with diazomethane followed by a CuCl-mediated coupling to (diethylphosphonyl) difluoromethylcadmium bromide. Moreover, treatment of L-4-iodoPhe-containing peptides under the same coupling conditions provided the F2Pmp-containing peptides in very good yields.

Enantioselective synthesis of N-Boc and N-Fmoc protected diethyl 4-phosphono(difluoromethyl)-L-phenylalanine; agents suitable for the solid-phase synthesis of peptides containing nonhydrolyzable analogues of O-phosphotyrosine

Enantioselective convergent syntheses of N-Boc and N-Fmoc protected diethyl 4-phosphono(difluoromethyl)-L-phenylalanine are reported.

Preparation of L-(Phosphonodifluoromethyl) phenylalanine derivatives as non-hydrolyzable mimetics of O-phosphotyrosine

N-t-BOC-L-(Phosphonodifluoromethyl)phenylalanine benzyl ester (1) was prepared in 5 steps from N-t-BOC-L-tyrosine benzyl eser O-triflate (4). Compound 1 was further converted to derivatives 2 and 3 which are potentially suitable for peptide synthesis. Ana