(S)-Benzyl 2-((tert-butoxycarbonyl)amino)-3-(4-hydroxyphenyl)propanoate

Base Information

• Chemical Name: (S)-Benzyl 2-((tert-butoxycarbonyl)amino)-3-(4-hydroxyphenyl)propanoate
• CAS No.: 19391-35-6
• Molecular Formula: C21H25 N O5
• Molecular Weight: 371.433
• DSSTox Substance ID: DTXSID70427063
• Nikkaji Number: J2.154.964I
• Wikidata: Q82239811
• Mol file: 19391-35-6.mol

Synonyms:19391-35-6;BOC-TYR-OBZL;(S)-Benzyl 2-((tert-butoxycarbonyl)amino)-3-(4-hydroxyphenyl)propanoate;Boc-L-tyrosine benzyl ester;N-Boc-L-tyrosine benzyl ester;Benzyl (tert-butoxycarbonyl)-L-tyrosinate;benzyl (2S)-3-(4-hydroxyphenyl)-2-[(2-methylpropan-2-yl)oxycarbonylamino]propanoate;BocTyrOBzl;Boc-L-Tyr-OBzl;N-t-Boc-O-benzyl-L-tyrosine;SCHEMBL1486267;DTXSID70427063;MFCD00190840;AKOS024258496;N-.alpha.-t-Boc-O-benzyl-L-tyrosine;HY-W111214;BS-15774;PD197266;PHORBOL12,13,20-TRIACETATE,4BETA;B5343;CS-0169323;N-(tert-Butoxycarbonyl)tyrosine benzyl ester;N-(tert-Butoxycarbonyl)-L-tyrosine Benzyl Ester;A880229;J-012556;Tyrosine, N-carboxy-, benzyl N-tert-butyl ester, L-;Tyrosine,N-carboxy-,benzyl N-tert-butyl ester,L-(8CI);(S)-Benzyl 2-(Boc-amino)-3-(4-hydroxyphenyl)propanoate;L-Tyrosine, N-[(1,1-dimethylethoxy)carbonyl]-, phenylmethyl ester;L-Tyrosine, N-[(1,1-dimethylethoxy)carbonyl]-O-(phenylmethyl)-;L-Tyrosine,N-[(1,1-dimethylethoxy)carbonyl]-,phenylmethyl ester;(S)-benzyl 2-(tert-butoxycarbonylamino)-3-(4-hydroxyphenyl)propanoate;Benzyl 2-[(tert-butoxycarbonyl)amino]-3-(4-hydroxyphenyl)propanoate #

Chemical Property of (S)-Benzyl 2-((tert-butoxycarbonyl)amino)-3-(4-hydroxyphenyl)propanoate

Chemical Property:

• Melting Point: 126.0 to 130.0 °C
• Boiling Point: 543.8±50.0 °C(Predicted)
• PKA: 9.74±0.15(Predicted)
• PSA: 84.86000
• Density: 1.186±0.06 g/cm3(Predicted)
• LogP: 3.96230
• Storage Temp.: Store at 0-5°C
• XLogP3: 4
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 9
• Exact Mass: 371.17327290
• Heavy Atom Count: 27
• Complexity: 474

Purity/Quality:

97% ^*data from raw suppliers

Boc-L-tyrosine benzyl ester ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: CC(C)(C)OC(=O)NC(CC1=CC=C(C=C1)O)C(=O)OCC2=CC=CC=C2
• Isomeric SMILES: CC(C)(C)OC(=O)N[C@@H](CC1=CC=C(C=C1)O)C(=O)OCC2=CC=CC=C2

Technology Process of (S)-Benzyl 2-((tert-butoxycarbonyl)amino)-3-(4-hydroxyphenyl)propanoate

There total 8 articles about (S)-Benzyl 2-((tert-butoxycarbonyl)amino)-3-(4-hydroxyphenyl)propanoate which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 91.2%

L-tyrosine benzyl ester (42406-77-9) + S-tert-butoxycarbonyl-4,6-dimethyl-2-mercaptopyrimidine (41840-28-2) → N-tert-butoxycarbonyl-L-tyrosine benzyl ester (19391-35-6)

Guidance literature:

With triethylamine; In 1,4-dioxane; water; for 24h; Ambient temperature;

Reference yield: 91.0%

Boc-Tyr-OH (3978-80-1) + benzyl bromide (100-39-0) → N-tert-butoxycarbonyl-L-tyrosine benzyl ester (19391-35-6)

Guidance literature:

Boc-Tyr-OH; With caesium carbonate; In N,N-dimethyl-formamide; at 25 ℃; for 1h;

benzyl bromide; In N,N-dimethyl-formamide; at 25 ℃; for 4h;

Reference yield: 81.0%

Boc-Tyr-OH (3978-80-1) + (4-hydroxyphenyl)(methyl)(benzyl)sulfonium chloride → N-tert-butoxycarbonyl-L-tyrosine benzyl ester (19391-35-6)

Guidance literature:

With potassium carbonate; In dichloromethane; for 8h; Ambient temperature;

DOI:10.1246/bcsj.69.1099

upstream raw materials:

L-tyrosine benzyl ester

S-tert-butoxycarbonyl-4,6-dimethyl-2-mercaptopyrimidine

Boc-Tyr-OH

benzyl bromide

Downstream raw materials:

[(S)-1-(4-Hydroxy-benzyl)-2-oxo-2-(2-thioxo-thiazolidin-3-yl)-ethyl]-carbamic acid tert-butyl ester

N-tert.-butoxycarbonyl-(4-trifluoromethanesulfonyloxy)-L-phenylalanine benzyl ester

O-tert-butyldimethylsilyl-N-Boc-D-tyrosine benzyl ester

(S)-2-tert-Butoxycarbonylamino-3-[4-(1-isopropyl-2-methyl-propoxycarbonyloxy)-phenyl]-propionic acid benzyl ester