Boc-L-Tyr(tBu)-OH Chemical Properties

Melting point:

113-118 °C

alpha 

-15 º (C=1% IN DMF)

Boiling point:

484.0±40.0 °C(Predicted)

Density 

1.116±0.06 g/cm3(Predicted)

storage temp. 

2-8°C

solubility 

Soluble in Chloroform,Dichloromethane,Ethyl Acetate,DMSO,Acetone,etc.

form 

powder to crystal

pka

3.00±0.10(Predicted)

color 

White to Almost white

optical activity

[α]20/D 15.0±1.0°, c = 1% in DMF

Water Solubility 

Soluble in DMF. Insoluble in water.

BRN 

4327336

InChI

InChI=1S/C18H27NO5/c1-17(2,3)23-13-9-7-12(8-10-13)11-14(15(20)21)19-16(22)24-18(4,5)6/h7-10,14H,11H2,1-6H3,(H,19,22)(H,20,21)/t14-/m0/s1

InChIKey

ZEQLLMOXFVKKCN-AWEZNQCLSA-N

SMILES

C(O)(=O)[C@H](CC1=CC=C(OC(C)(C)C)C=C1)NC(OC(C)(C)C)=O

CAS DataBase Reference

47375-34-8(CAS DataBase Reference)

Safety Information

WGK Germany 

3

HS Code 

29242990

MSDS

• Language:English Provider:SigmaAldrich

Boc-L-Tyr(tBu)-OH Usage And Synthesis

Chemical Properties

White powder

Uses

N-Boc-O-tert-butyl-L-tyrosine (Boc-L-Tyr(tBu)-OH) is used as pharmaceutical intermediate.

Application

Boc-Tyr(tBu)-OH is an important organic reagent that can be used as a building block for the synthesis of many organic compounds. This compound could be used as a starting material to synthesize TPE-Tyr. TPE-Tyr can undergo covalent crosslinking via the formation of dityrosine linkages by exploiting horseradish peroxidase (HRP)-catalyzed phenol polymerization in the presence of H2O2, thereby activating the AIE process and switching on fluorescence emission of TPE core motif[1].

Synthesis

O-tert-butyl-L-tyrosine (2.00 g, 8.42 mmol, 1.0 equiv.) and di-tert-butyl dicarbonate (2.20 g, 10.10 mmol, 1.2 equiv.) were dissolved in a mixture of THF (15 mL) and NaOH (1 N, 30 mL) and stirred at room temperature for 10 h. THF was removed under reduced pressure, and the pH of residual solution was adjusted to 3.0 with dilute hydrochloric acid and the crude product was extracted by ethyl acetate. The combined organic phases was washed with saturated brine (pH 3.0) and dried over anhydrous Na2SO4. The organic solvent was removed under reduced pressure and dried in a vacuum oven at room temperature overnight, affording (N-Boc-O-tert-butyl)-L-Tyr (Boc-O-tert-butyl-L-tyrosine) as a yellowish solid (2.64 g, 93%)[1].

References

[1] Wang X, et al. Highly Selective Fluorogenic Multianalyte Biosensors Constructed via Enzyme-Catalyzed Coupling and Aggregation-Induced Emission. Journal of the American Chemical Society, 2014; 136: 9890–9893.

Boc-L-Tyr(tBu)-OH(47375-34-8)Related Product Information

• tert-Butanol
• tert-Butyl hydroperoxide
• tert-Butyl methyl ether
• BUTYL OLEATE
• 4-tert-Butylcatechol
• L-Tyrosine
• Cyhalofop-butyl
• 4-tert-Butylphenol
• Boc-Aib-OH
• Boc-D-Tyr-OH
• tert-Butyldimethylsilyl chloride
• Buprofezin
• Methyl 4-tert-butylbenzoate
• TYROSINASE
• Dibutyl phthalate
• BOC-GLY-LEU-OH
• Boc-Tyr(Me)-OH
• O-METHYL-D-TYROSINE