O-TERT-BUTYLDIMETHYLSILYL-N-METHYL-N-T-BUTOXYCARBONYL-L-TYROSINE, METHYL ESTER

Base Information

• Chemical Name: O-TERT-BUTYLDIMETHYLSILYL-N-METHYL-N-T-BUTOXYCARBONYL-L-TYROSINE, METHYL ESTER
• CAS No.: 112196-58-4
• Molecular Formula: C22H37NO5Si
• Molecular Weight: 423.625
• DSSTox Substance ID: DTXSID70461806
• Nikkaji Number: J1.567.524A
• Wikidata: Q82286224
• Mol file: 112196-58-4.mol

Synonyms:O-tert-Butyldimethylsilyl-N-methyl-N-t-butoxycarbonyl-L-tyrosine,Methyl Ester;Boc-(S)-N-MeTyr(TBS)-OMe;N-[(1,1-dimethylethoxy)carbonyl]-O-[(1,1-dimethylethyl)dimethylsilyl]-N-methyl-L-tyrosine Methyl Ester;

Chemical Property of O-TERT-BUTYLDIMETHYLSILYL-N-METHYL-N-T-BUTOXYCARBONYL-L-TYROSINE, METHYL ESTER

Chemical Property:

• Vapor Pressure: 1.23E-08mmHg at 25°C
• Boiling Point: 459.7oC at 760 mmHg
• PKA: -1.69±0.70(Predicted)
• Flash Point: 231.8oC
• PSA: 65.07000
• Density: 1.03g/cm3
• LogP: 5.02160
• Solubility.: Dichloromethane, Ethyl Acetate
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 10
• Exact Mass: 423.24409982
• Heavy Atom Count: 29
• Complexity: 557

Purity/Quality:

98%Min ^*data from raw suppliers

O-tert-Butyldimethylsilyl-N-methyl-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)N(C)C(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)[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-METHYL-N-T-BUTOXYCARBONYL-L-TYROSINE, METHYL ESTER

There total 12 articles about O-TERT-BUTYLDIMETHYLSILYL-N-METHYL-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: 94.0%

methyl iodide (74-88-4) + Boc-(S)-N-Me-Tyr(TBS)-OH (848780-45-0) → (S)-methyl-2-((tert-butoxycarbonyl)(methyl)amino)-3-(4-((tert-butyldimethyl-silyl)oxy)phenyl)propanoate (112196-58-4)

Guidance literature:

With potassium hydrogencarbonate; In N,N-dimethyl-formamide; at 0 - 20 ℃; for 13h;

DOI:10.1016/j.tet.2004.12.009

Reference yield: 87.0%

methyl (S)-2-((tert-butoxycarbonyl)amino)-3-(4-((tert-butyldimethylsilyl)-oxy)phenyl)propanoate (112196-57-3) + methyl iodide (74-88-4) → (S)-methyl-2-((tert-butoxycarbonyl)(methyl)amino)-3-(4-((tert-butyldimethyl-silyl)oxy)phenyl)propanoate (112196-58-4)

Guidance literature:

With sodium hydride; In N,N-dimethyl-formamide; at 25 ℃; for 48h;

DOI:10.1021/jo00238a005

Reference yield:

(S)-N-(tert-butoxycarbonyl)tyrosine methyl ester (4326-36-7) → (S)-methyl-2-((tert-butoxycarbonyl)(methyl)amino)-3-(4-((tert-butyldimethyl-silyl)oxy)phenyl)propanoate (112196-58-4)

Guidance literature:

Multi-step reaction with 2 steps

1: 93 percent / imidazole / dimethylformamide / 6 h / 25 °C

2: 87 percent / NaH / dimethylformamide / 48 h / 25 °C

With 1H-imidazole; sodium hydride; In N,N-dimethyl-formamide;

DOI:10.1021/jo00238a005

upstream raw materials:

methyl (S)-2-((tert-butoxycarbonyl)amino)-3-(4-((tert-butyldimethylsilyl)-oxy)phenyl)propanoate

methyl iodide

Boc-(S)-N-Me-Tyr(TBS)-OH

Boc-Tyr-OH

Downstream raw materials:

methyl N-(tert-butoxycarbonyl)-N-methyl-L-tyrosinate

Boc-(S)-Phe-(S)-N-Me-Tyr-OMe

Boc-(S)-Phe-(S)-N-Me-Tyr(TBS)-OMe

Boc-(S)-Phs(Bn)-(S)-Phe-(S)-N-Me-Tyr-OMe