191087-23-7

Basic information

• Product Name: 2-(~18~F)fluoro-5-hydroxy-L-tyrosine
• CAS NO: 191087-23-7
• Molecular Formula: C₉H₁₀¹⁸FNO₄
• Molecular Weight: 214.1809
• Mol File: 191087-23-7.mol

Chemical Properties

• Density: 1.553g/cm³
• Refractive Index: 1.629
• CAS DataBase Reference: 2-(~18~F)fluoro-5-hydroxy-L-tyrosine(CAS DataBase Reference)
• NIST Chemistry Reference: 2-(~18~F)fluoro-5-hydroxy-L-tyrosine(191087-23-7)
• EPA Substance Registry System: 2-(~18~F)fluoro-5-hydroxy-L-tyrosine(191087-23-7)

Safety Data

• Hazardous Substances Data: 191087-23-7(Hazardous Substances Data)

Upstream product

• 63-84-3 dopa 
• 56-40-6 glycine 
• 169267-05-4 C₂₀H₂₀⁽¹⁸⁾FNO₄ 
• 129841-03-8 3,4-methylenedioxy-6-[18F]flourobenzyl bromide 
• 90473-00-0 <(+)-2-hydroxypipanyl-3-idene>glycine ethyl ester 
• 5796-17-8 D-Dopa 
• 81477-94-3 N-(diphenylmethylene)glycine tert-butyl ester 
• 1644527-25-2 C₂₃H₃₄⁽¹⁸⁾FNO₈ 
• 1614253-58-5 (S)-tert-butyl-(S)-2-(tritylamino)-3-(5-formyl-4-methoxymethoxy-2-nitro-phenyl)-propionate 
• 1421282-70-3 N-(tert-butoxycarbonyl)-3,4-di(tert-butoxycarbonyloxy)-6-[¹⁸F]fluoro-L-phenylalanine methyl ester 

Downstream Products

• 92812-82-3 [18F]-L-3,4-dihydroxy-6-fluorophenylalanine 

Relevant articles and documents

Cu-Mediated Radiofluorination of Aryl Pinacolboronate Esters: Alcohols as Solvents with Application to 6-L-[18F]FDOPA Synthesis

Cu-mediated radiofluorination of arylboronic acid pinacol esters (ArylBPin) using Cu(OTf)2(Py)4 complex is a useful approach for the introduction of [18F]fluorine into non-activated arenes and heteroarenes. Owing to the co

Direct arene C–H fluorination with 18F? via organic photoredox catalysis

Positron emission tomography (PET) plays key roles in drug discovery and development, as well as medical imaging. However, there is a dearth of efficient and simple radiolabeling methods for aromatic C–H bonds, which limits advancements in PET radiotracer

One-pot synthesis of high molar activity 6-[18F]fluoro-l-DOPA by Cu-mediated fluorination of a BPin precursor

A one-pot two-step synthesis of 6-[18F]fluoro-l-DOPA ([18F]FDOPA) has been developed involving Cu-mediated radiofluorination of a pinacol boronate ester precursor. The method is fully automated, provides [18F]FDOPA in good

L-dopa precursor compound, preparation method thereof, and preparation method of 18F labeled L-dopa using the same

The present invention relates to an L-dopa precursor compound, a preparation method thereof, and a preparation method of an ^18F labeled L-dopa using the same. The preparation method of the ^18F labeled L-dopa comprises a step of preparing a compound repr

Base/Cryptand/Metal-Free Automated Nucleophilic Radiofluorination of [18F]FDOPA from Iodonium Salts: Importance of Hydrogen Carbonate Counterion

As evidenced by the number of publications and patents published in the last years, the radiosynthesis of 6-[18F]fluoro-3,4-dihydroxy-L-phenylalanine ([18F]FDOPA) using the nucleophilic [18F]F- process remains currently a challenge for the radiochemists scientific community even if promising methods for the radiofluorination of electron-rich aromatic structures were recently developed from arylboronate, arylstannane or iodonium salt precursors. In such context, based on the use of an iodonium triflate salt precursor, we optimized a fast and efficient radiofluorination route fully automated and free from any base, cryptand or metal catalyst for the radiosynthesis of [18F]FDOPA. Using this method, this clinically relevant radiotracer was produced in 64 min, 27–38 % RCY d.c. (n = 5), >99 % RCP, >99 % ee., and high Am 170–230 GBq/μmol. In addition, this optimization study clearly highlighted the important role of a triflate-hydrogen carbonate counterion exchange during the radiolabeling process to achieve high fluorine-18 incorporation yields.

Novel preparation method for positron medicine [18F]FDOPA and intermediate thereof

The invention relates to a novel preparation method for a positron medicine [18F]FDOPA and an intermediate thereof, and in particular to a synthesis method for [18F]FDOPA. The preparation method includes the following steps: (img file ='DDA0001356857630000011.TIF' wi='1718' he='312'/) (1) a compound as formula I reacts with an appropriate 18F source to generate a compound as formula II; (2) the compound as formula II undergoes deprotection operation to generate [18F]FDOPA; R1 and R2 are respectively hydroxyl protecting groups; R3 is chosen from any one of halogen-substituted alkyl group and aryl group, or two R3s are formed together into a 5-8-membered ring; R4 is a carboxyl protecting group; and R5 an R6 are respectively chosen from H and an amino protecting group.

A practical method for the preparation of 18F-labeled aromatic amino acids from nucleophilic [18F]fluoride and stannyl precursors for electrophilic radiohalogenation

In a recent contribution of Scott et al., the substrate scope of Cu-mediated nucleophilic radiofluorination with [18F]KF for the preparation of 18F-labeled arenes was extended to aryland vinylstannanes. Based on these findings, the potential of this reaction for the production of clinically relevant positron emission tomography (PET) tracers was investigated. To this end, Cu-mediated radiofluorodestannylation using trimethyl(phenyl)tin as a model substrate was re-evaluated with respect to different reaction parameters. The resulting labeling protocol was applied for 18F-fluorination of different electron-rich, -neutral and -poor arylstannyl substrates in RCCs of 16-88%. Furthermore, this method was utilized for the synthesis of 18F-labeled aromatic amino acids from additionally N-Boc protected commercially available stannyl precursors routinely applied for electrophilic radiohalogenation. Finally, an automated synthesis of 6-[18F]fluoro-L-m-tyrosine (6-[18F]FMT), 2-[18F]fluoro-L-tyrosine (2-[18F]F-Tyr), 6-[18F]fluoro-L-3, 4-dihydroxyphenylalanine (6-[18F]FDOPA) and 3-O-methyl-6-[18F]FDOPA ([18F]OMFD) was established furnishing these PET probes in isolated radiochemical yields (RCYs) of 32-54% on a preparative scale. Remarkably, the automated radiosynthesis of 6-[18F]FDOPA afforded an exceptionally high RCY of 54 5% (n = 5).

Alcohol-Enhanced Cu-Mediated Radiofluorination

The potential of many 18F-labeled (hetero)aromatics for applications in positron emission tomography remains underexplored because convenient procedures for their radiosynthesis are lacking. Consequently, simple methods to prepare radiofluorinated (hetero)arenes are highly sought after. Herein, we report the beneficial effect of primary and secondary alcohols on Cu-mediated 18F-labeling. This observation contradicts the assumption that such alcohols are inappropriate solvents for aromatic fluorination. Therefore, we developed a protocol for rapid radiolabeling of an extraordinarily broad scope of boronic and stannyl substrates under general reaction conditions. Notably, radiofluorinated indoles, phenols, and anilines were synthesized directly from the corresponding unprotected precursors. Furthermore, the novel method enabled the preparation of radiofluorinated tryptophans, [18F]F-DPA, [18F]DAA1106, 6-[18F]FDA, and 6-[18F]FDOPA.

Use of SF6 for the production of electrophilic 18F-fluorination reagents

Electrophilic 18F-fluorination is an important method for production of tracers for positron emission tomography. The most commonly employed 18F-fluorination reagents [18F]F2, [18F]Selectfluor bis(tri

Method for preparing [18F]Fluoro-L-Dopa with high radiochemical and enantiomeric purity

The present invention relates to a manufacturing method and a purifying method of [^18f] fluoro-L-dopa with high purity and high specific radioactivity, which is automatically manufactured wherein the [^18f] fluoro-L-dopa requires at least one solution process in each manufacturing step and accordingly has good reproducibility and stable yield, thereby being used in an auto-manufacturing apparatus, and is purified by using a high performance liquid chromatography which uses a solid phase extraction method and chiral column, thereby having good high purity and high specific radioactivity.