Z-Tyr(tbu)-ome

Base Information

• Chemical Name: Z-Tyr(tbu)-ome
• CAS No.: 5068-29-1
• Molecular Formula: C22H27 N O5
• Molecular Weight: 385.46
• Hs Code.: 2924299090
• DSSTox Substance ID: DTXSID101147616
• Nikkaji Number: J1.167.061J
• Mol file: 5068-29-1.mol

Synonyms:Z-TYR(TBU)-OME;5068-29-1;(S)-Methyl 2-(((benzyloxy)carbonyl)amino)-3-(4-(tert-butoxy)phenyl)propanoate;methyl (2S)-3-[4-[(2-methylpropan-2-yl)oxy]phenyl]-2-(phenylmethoxycarbonylamino)propanoate;Z-Tyr(But)-OMe;Cbz-O-tert-butyl-L-tyrosine methyl ester;O-(1,1-Dimethylethyl)-N-[(Phenylmethoxy)Carbonyl]-L-Tyrosine Methyl Ester;SCHEMBL13919532;IPRNNTJYTNRIDM-IBGZPJMESA-N;DTXSID101147616;MFCD00237370;Z-O-t-Butyl-L-tyrosine methyl ester;AKOS015913833;AS-10569;CS-0186191;D95804;N-(Benzyloxycarbonyl)-O-tert-butyl-L-tyrosine methyl ester;(S)-methyl 2-(benzyloxycarbonylamino)-3-(4-tert-butoxyphenyl)propanoate;L-Tyrosine,o-(1,1-dimethylethyl)-N-[(phenylmethoxy)carbonyl]-,methyl ester;(S)-Methyl2-(((benzyloxy)carbonyl)amino)-3-(4-(tert-butoxy)phenyl)propanoate;Methyl (S)-2-(((benzyloxy)carbonyl)amino)-3-(4-(tert-butoxy)phenyl)propanoate

Chemical Property of Z-Tyr(tbu)-ome

Chemical Property:

• Boiling Point: 529.8±50.0 °C(Predicted)
• PKA: 10.81±0.46(Predicted)
• PSA: 73.86000
• Density: 1.138±0.06 g/cm3(Predicted)
• LogP: 4.26530
• Storage Temp.: -15°C
• XLogP3: 3.8
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 10
• Exact Mass: 385.18892296
• Heavy Atom Count: 28
• Complexity: 488

Purity/Quality:

98%Min ^*data from raw suppliers

Z-O-tert-butyl-L-tyrosine methyl ester 99+% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C)(C)OC1=CC=C(C=C1)CC(C(=O)OC)NC(=O)OCC2=CC=CC=C2
• Isomeric SMILES: CC(C)(C)OC1=CC=C(C=C1)C[C@@H](C(=O)OC)NC(=O)OCC2=CC=CC=C2

Technology Process of Z-Tyr(tbu)-ome

There total 7 articles about Z-Tyr(tbu)-ome 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: 89.0%

N-(benzyloxycarbonyl)-L-tyrosine methyl ester (13512-31-7) + isobutene (115-11-7,15220-85-6) → 2-benzyloxycarbonylamino-3-(4-tert-butoxy-phenyl)-propionic acid methyl ester (5068-29-1)

Guidance literature:

With sulfuric acid; In dichloromethane; for 36h; Ambient temperature;

DOI:10.1021/jo961447m

Reference yield:

L-Tyr-OMe (1080-06-4) → 2-benzyloxycarbonylamino-3-(4-tert-butoxy-phenyl)-propionic acid methyl ester (5068-29-1)

Guidance literature:

Multi-step reaction with 2 steps

1: 98 percent / Na₂CO₃ / CH₂Cl₂; H₂O / 2.5 h / 0 - 20 °C

2: 89 percent / H₂SO₄ / CH₂Cl₂ / 36 h / Ambient temperature

With sulfuric acid; sodium carbonate; In dichloromethane; water;

DOI:10.1021/jo961447m

Reference yield:

L-tyrosine (60-18-4,18875-48-4,25619-78-7,30704-25-7) → 2-benzyloxycarbonylamino-3-(4-tert-butoxy-phenyl)-propionic acid methyl ester (5068-29-1)

Guidance literature:

Multi-step reaction with 3 steps

1: 100 percent / SOCl₂ / 1.) room temperature, 2 h, 2.) reflux, 0.5 h

2: 98 percent / Na₂CO₃ / CH₂Cl₂; H₂O / 2.5 h / 0 - 20 °C

3: 89 percent / H₂SO₄ / CH₂Cl₂ / 36 h / Ambient temperature

With thionyl chloride; sulfuric acid; sodium carbonate; In dichloromethane; water;

DOI:10.1021/jo961447m

upstream raw materials:

N-(benzyloxycarbonyl)-L-tyrosine methyl ester

isobutene

L-tyrosine methyl ester HCl

L-tyrosine

Downstream raw materials:

N-(benzyloxycarbonyl)-O-(1,1-dimethylethyl)-L-tyrosine

C₁₄H₂₃NO₂

[1-(4-tert-butoxy-benzyl)-2-methoxy-ethyl]-carbamic acid benzyl ester

methyl 2(S)-<(tert-butyloxycarbonyl)amino>-3-<(4-tert-butyloxy)phenyl>propanoate

Refernces

• 1、 Bastiaans, Harold M.M.,Van der Baan, Juul L.,Ottenheijm, Harry C.J.. "Flexible and convergent total synthesis of cyclotheonamide B". . p. 3880 - 3889. Retrieved 2007/10/03.