O-tert-Butyldimethylsilyl-N-t-butoxycarbonyl-L-tyrosine, Methyl Ester

Base Information

• Chemical Name: O-tert-Butyldimethylsilyl-N-t-butoxycarbonyl-L-tyrosine, Methyl Ester
• CAS No.: 112196-57-3
• Molecular Formula: C21H35NO5Si
• Molecular Weight: 409.598
• DSSTox Substance ID: DTXSID90442293
• Mol file: 112196-57-3.mol

Synonyms:112196-57-3;O-tert-Butyldimethylsilyl-N-t-butoxycarbonyl-L-tyrosine, Methyl Ester;methyl (2S)-3-[4-[tert-butyl(dimethyl)silyl]oxyphenyl]-2-[(2-methylpropan-2-yl)oxycarbonylamino]propanoate;DTXSID90442293;BPHHRKYVWXIBMQ-KRWDZBQOSA-N;AKOS030241560;J-002725

Chemical Property of O-tert-Butyldimethylsilyl-N-t-butoxycarbonyl-L-tyrosine, Methyl Ester

Chemical Property:

• Vapor Pressure: 0mmHg at 25°C
• Boiling Point: 468.468oC at 760 mmHg
• PKA: 11.02±0.46(Predicted)
• Flash Point: 237.121oC
• PSA: 77.35000
• Density: 1.033g/cm3
• LogP: 4.88380
• Solubility.: Ethyl Acetate, Methanol
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 10
• Exact Mass: 409.22844975
• Heavy Atom Count: 28
• Complexity: 528

Purity/Quality:

98%Min ^*data from raw suppliers

O-tert-Butyldimethylsilyl-N-t-butoxycarbonyl-L-tyrosine, methyl ester ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

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

Technology Process of O-tert-Butyldimethylsilyl-N-t-butoxycarbonyl-L-tyrosine, Methyl Ester

There total 6 articles about O-tert-Butyldimethylsilyl-N-t-butoxycarbonyl-L-tyrosine, Methyl Ester 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: 99.0%

(S)-N-(tert-butoxycarbonyl)tyrosine methyl ester (4326-36-7) + tert-butyldimethylsilyl chloride (18162-48-6) → methyl (S)-2-((tert-butoxycarbonyl)amino)-3-(4-((tert-butyldimethylsilyl)-oxy)phenyl)propanoate (112196-57-3)

Guidance literature:

With 1H-imidazole; In N,N-dimethyl-formamide; at 20 ℃; for 6h;

Reference yield:

L-Tyr-OMe (1080-06-4) → methyl (S)-2-((tert-butoxycarbonyl)amino)-3-(4-((tert-butyldimethylsilyl)-oxy)phenyl)propanoate (112196-57-3)

Guidance literature:

Multi-step reaction with 2 steps

1: 72 percent / tetrahydrofuran / 2 h / 25 °C

2: 93 percent / imidazole / dimethylformamide / 6 h / 25 °C

With 1H-imidazole; In tetrahydrofuran; N,N-dimethyl-formamide;

DOI:10.1021/jo00238a005

Reference yield:

L-tyrosine (60-18-4,18875-48-4,25619-78-7,30704-25-7) → methyl (S)-2-((tert-butoxycarbonyl)amino)-3-(4-((tert-butyldimethylsilyl)-oxy)phenyl)propanoate (112196-57-3)

Guidance literature:

Multi-step reaction with 3 steps

1: 95 percent / HCl (gas) / 2 h / 25 °C

2: 72 percent / tetrahydrofuran / 2 h / 25 °C

3: 93 percent / imidazole / dimethylformamide / 6 h / 25 °C

With 1H-imidazole; hydrogenchloride; In tetrahydrofuran; N,N-dimethyl-formamide;

DOI:10.1021/jo00238a005

upstream raw materials:

(S)-N-(tert-butoxycarbonyl)tyrosine methyl ester

tert-butyldimethylsilyl chloride

L-Tyr-OMe

L-tyrosine

Downstream raw materials:

sodium salt of tert-butyloxycarbonyl-O-sulfotyrosine α-methyl ester

(S)-2-(2-N-tert-butoxycarbonylamino)-3-[4-(tert-butyldimethylsilyloxy)phenyl]-propanoic acid

Refernces

• 1、 Ferraro, Samantha L.,Flynn, James P.,Hwang, Seung,Liu, Chao,Niu, Jia,Yang, Cangjie. "A General Approach to O-Sulfation by a Sulfur(VI) Fluoride Exchange Reaction". supporting information. p. 18435 - 18441. Retrieved 2020/08/25.
• 2、 -. "TYROSINE AMIDE DERIVATIVES AS RHO- KINASE INHIBITORS". Paragraph 0470-0471. . Retrieved 2018/08/20.