203398-44-1

Basic information

• Product Name: N-(tert-butoxycarbonyl)-3,4-di(tert-butoxycarbonyloxy)-L-phenylalanine ethyl ester
• Synonyms: N-(tert-butoxycarbonyl)-3,4-di(tert-butoxycarbonyloxy)-L-phenylalanine ethyl ester
• CAS NO: 203398-44-1
• Molecular Weight: 525.596
• Mol File: 203398-44-1.mol
• Article Data: 5

Chemical Properties

• CAS DataBase Reference: N-(tert-butoxycarbonyl)-3,4-di(tert-butoxycarbonyloxy)-L-phenylalanine ethyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: N-(tert-butoxycarbonyl)-3,4-di(tert-butoxycarbonyloxy)-L-phenylalanine ethyl ester(203398-44-1)
• EPA Substance Registry System: N-(tert-butoxycarbonyl)-3,4-di(tert-butoxycarbonyloxy)-L-phenylalanine ethyl ester(203398-44-1)

Safety Data

• Hazardous Substances Data: 203398-44-1(Hazardous Substances Data)

Upstream product

• 24424-99-5 di-tert-butyl dicarbonate 
• 37178-37-3 L-DOPA ethyl ester 
• 39740-30-2 ethyl (S)-2-amino-3-(3,4-dihydroxyphenyl)propanoate hydrochloride 
• 59-92-7 levodopa 

Downstream Products

• 1421282-51-0 N-(tert-butoxycarbonyl)-3,4-di(tert-butoxycarbonyloxy)-6-fluoro-L-phenylalanine ethyl ester 

Relevant articles and documents

6-[18F]Fluoro-L-DOPA by radiofluorodestannylation : A short and simple synthesis of a new labelling precursor

This paper describes a short and simple synthesis of a new fully protected stannylated precursor, namely N-(tert-butoxycarbonyl)-3,4-di(tert-butoxycarbonyloxy)-6-trimethylstannyl-L -phenylalanine ethyl ester, for the preparation of 6-[18F]fluoro-L-DOPA, used routinely in our Positron Emission Tomography program on neurodegenerative diseases as a tracer of the cerebral dopamine metabolism. The chemical pathway described for the total synthesis of our labelling precursor uses a straightforward protection sequence. This 4-step chemical synthesis allows the rapid preparation of several grammes of pure material in good overall yield. Regioselective radiofluorodestannylation using [18F]fluorine ([18F]F2, cyclotron-produced isotope, half-life : 110 min) gave pure 6-[18F]fluoro-L- DOPA (8) in good radiochemical yield (26% decay-corrected, based on starting [18F]fluorine recovered from the target) in 45-50 min after the End of Bombardment. The product was found to be >99% chemically, radiochemically and enantiomerically pure.

Fluorination of an arylboronic ester using [18F]selectfluor bis(triflate): Application to 6-[18F]fluoro-l-DOPA

The Ag-mediated electrophilic [18F]fluorination of an arylboronic ester is reported. This new radiochemical transformation uses [ 18F]selectfluor bis(triflate) in acetone. The process gave 6-[ 18F]fluoro-l-DOPA with a RCY of 19 ± 12% and a specific activity of 2.6 ± 0.3 GBq μmol-1.

NO-CARRIER-ADDED NUCLEOPHILIC [F-18] FLUORINATION OF AROMATIC COMPOUNDS

Phenyliodonium ylide derivatives substituted with electron donating as well as electron withdrawing groups on the aromatic ring are shown for use as precursors in aromatic nucleophilic substitution reactions. The iodonium ylide group is substituted by nucleophiles such as halide ions to provide the corresponding haloaryl derivatives. No- carrier-added [F-18]fluoride ion exclusively substitutes the iodonium ylide moiety in these derivatives and provides high specific activity F- 18 labeled fluoro derivatives. Protected L-dopa-6-iodonium ylide derivative have been synthesized as a precursors for the preparation of no-carrier-added 6-[F- 18]fluoro-L-dopa. The iodonium ylide group in this L-dopa.derivative is nucleophilically substituted by no-carrier-added [F-18]fluoride ion to provide a [F-18]fluoro intermediates which upon acid hydrolysis yielded 6-[F- 18]fluoro-L-dopa.