3799-87-9

Basic information

• Product Name: methyl (2,2,2-trifluoroacetyl)-L-tyrosinate
• CAS NO: 3799-87-9
• Molecular Weight: 291.227
• Mol File: 3799-87-9.mol

Chemical Properties

• CAS DataBase Reference: methyl (2,2,2-trifluoroacetyl)-L-tyrosinate(CAS DataBase Reference)
• NIST Chemistry Reference: methyl (2,2,2-trifluoroacetyl)-L-tyrosinate(3799-87-9)
• EPA Substance Registry System: methyl (2,2,2-trifluoroacetyl)-L-tyrosinate(3799-87-9)

Safety Data

• Hazardous Substances Data: 3799-87-9(Hazardous Substances Data)

Upstream product

• 431-47-0 trifluoroacetic acid-methyl ester 
• 1080-06-4 L-Tyr-OMe 
• 186581-53-3 diazomethane 
• 350-10-7 N-trifluorosulfonyl-L-tyrosine 
• 3417-91-2 L-tyrosine methyl ester HCl 
• 407-25-0 trifluoroacetic anhydride 
• 60-18-4 L-tyrosine 

Downstream Products

• 350-10-7 N-trifluorosulfonyl-L-tyrosine 
• 67521-59-9 Tfa-L-Tyr(cHex)-OMe 
• 1373931-85-1 (2S)-methyl 3-(4-(2-(t-butoxy)-1-(4,5-dimethoxy-2-nitrophenyl)-2-oxoethoxy)phenyl)-2-(2,2,2-trifluoroacetamido)propanoate 
• 60-18-4 L-tyrosine 
• 1013883-02-7 FMOC-4-[2-(Boc-aminoethoxy)]-L-phenylalanine 
• 32795-52-1 β-p-ethoxyphenyl-β-alanine 

Relevant articles and documents

Preparation method of L-tyrosine derivative

The invention discloses a preparation method of an L-tyrosine derivative. The L-tyrosine derivative is O-alkyl-N-[fluorenylmethoxycarbonyl]-L-tyrosine, L-tyrosine is used as a starting material, the O-alkyl-N-[fluorenylmethoxycarbonyl]-L-tyrosine is prepared through esterification, amidation, etherification/hydrolysis and amidation in sequence, the total yield of the target product can reach 61.5%, and the ee value can reach 99% or above. The preparation method disclosed by the invention has the advantages of cheap and easily available raw materials, lower cost and the like, for example, separation of triphenylphosphine oxide is avoided through etherification reaction. The method has the advantages of simple process, short route, mild reaction conditions and the like, for example, etherification and hydrolysis adopt a one-pot method; and the whole technological process generates few three wastes, the product yield and purity are high, and the method is suitable for industrial production.

Discovery of Modified Amidate (ProTide) Prodrugs of Tenofovir with Enhanced Antiviral Properties

This study describes the discovery of novel prodrugs bearing tyrosine derivatives instead of the phenol moiety present in FDA-approved tenofovir alafenamide fumarate (TAF). The synthesis was optimized to afford diastereomeric mixtures of novel prodrugs in

Click-to-Release from trans-Cyclooctenes: Mechanistic Insights and Expansion of Scope from Established Carbamate to Remarkable Ether Cleavage

The bioorthogonal cleavage of allylic carbamates from trans-cyclooctene (TCO) upon reaction with tetrazine is widely used to release amines. We disclose herein that this reaction can also cleave TCO esters, carbonates, and surprisingly, ethers. Mechanistic studies demonstrated that the elimination is mainly governed by the formation of the rapidly eliminating 1,4-dihydropyridazine tautomer, and less by the nature of the leaving group. In contrast to the widely used p-aminobenzyloxy linker, which affords cleavage of aromatic but not of aliphatic ethers, the aromatic, benzylic, and aliphatic TCO ethers were cleaved as efficiently as the carbamate, carbonate, and esters. Bioorthogonal ether release was demonstrated by the rapid uncaging of TCO-masked tyrosine in serum, followed by oxidation by tyrosinase. Finally, tyrosine uncaging was used to chemically control cell growth in tyrosine-free medium.

Photochemical trifluoromethylation of tyramine and L-tyrosine derivatives

Ultraviolet irradation (254 nm) of methanolic solutions of trifluoromethyl iodide (CF3I) in the presence of side-chain-protected tyramine and L-tyrosine results in trifluoromethylation of the aromatic ring.The presence of an amine base to neutralize HI formed during the reaction is essential.The electrophilic trifluoromethyl radical preferentially attacks the ring ortho to the phenolic group, and 3-trifluoromethyltyramine and 3-trifluoromethyl-L-tyrosine derivatives were obtained in yields of 27percent and 33percent, respectively.

SOLID PHASE SYNTHESIS OF TYROSINE-CONTAINING HISTONE FRAGMENTS

The solid phase synthesis of Ac-Val-Val-Tyr-Ala-Leu-OH (1), Ac-Glu-Ala-Tyr-Leu-Val-OH (2) and Ac-Leu-Tyr-Gly-Phe-Gly-Gly-OH (3), segments 86-90 of histone H4, 97-101 of histone H3 and 97-102 of histone H4, respectively, is described using chloromethylresin and chloromethyl-Pab-resin as solid supports.In the synthesis of peptides 2 and 3 using 2,6-dichlorobenzyl ether as tyrosine side chain protection, 7percent and 8percent of the 3-dichlorobenzyltyrosine-rearranged peptide could be isolated by Bio-Gel P-2 or diethylaminoethylcellulose chromatography.Alternative use of cyclohexyl ether as tyrosine protection has been explored with satisfactory results.