Boc-D-Tyr(Et)-OH

Base Information

• Chemical Name: Boc-D-Tyr(Et)-OH
• CAS No.: 76757-92-1
• Molecular Formula: C16H23 N O5
• Molecular Weight: 309.362
• DSSTox Substance ID: DTXSID50426918
• Wikidata: Q72449252
• Mol file: 76757-92-1.mol

Synonyms:Boc-D-Tyr(Et)-OH;76757-92-1;Boc-O-ethyl-D-tyrosine;N-Boc-O-ethyl-D-tyrosine;(2R)-3-(4-ethoxyphenyl)-2-[(2-methylpropan-2-yl)oxycarbonylamino]propanoic acid;D-Tyrosine, N-[(1,1-dimethylethoxy)carbonyl]-O-ethyl-;MFCD00065602;SCHEMBL3188805;DTXSID50426918;NCLAAKQIHUIOIV-CYBMUJFWSA-N;AKOS015836443;DS-9767;N-(tert-butoxycarbonyl)-O-ethyl-D-tyrosine;CS-0151470;N12217;A865422;(R)-2-(tert-butoxycarbonylamino)-3-(4-ethoxyphenyl)propanoic acid;N-alpha-t-Butyloxycarbonyl-O-ethyl-D-tyrosine (Boc-D-Tyr(Et)-OH);(R)-2-((tert-butoxycarbonyl)amino)-3-(4-ethoxyphenyl)propanoic acid

Chemical Property of Boc-D-Tyr(Et)-OH

Chemical Property:

• Melting Point: 80-81 °C
• Boiling Point: 472.7±40.0 °C(Predicted)
• PKA: 2.99±0.10(Predicted)
• PSA: 84.86000
• Density: 1.149±0.06 g/cm3(Predicted)
• LogP: 2.99660
• Storage Temp.: Store at RT.
• XLogP3: 2.1
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 8
• Exact Mass: 309.15762283
• Heavy Atom Count: 22
• Complexity: 369

Purity/Quality:

98%min ^*data from raw suppliers

Boc-O-ethyl-D-tyrosine ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCOC1=CC=C(C=C1)CC(C(=O)O)NC(=O)OC(C)(C)C
• Isomeric SMILES: CCOC1=CC=C(C=C1)C[C@H](C(=O)O)NC(=O)OC(C)(C)C
• Uses: Boc-O-ethyl-D-tyrosine,

Technology Process of Boc-D-Tyr(Et)-OH

There total 7 articles about Boc-D-Tyr(Et)-OH 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: 63.0%

diethyl sulfate (64-67-5) + N-(tert-butoxycarbonyl)-D-tyrosine (70642-86-3) → (R)-2-((tert-butoxycarbonyl)amino)-3-(4-ethoxyphenyl)propanoic acid (76757-92-1,247088-44-4)

Guidance literature:

With crown ether; In benzene; for 1.5h;

DOI:10.1021/jm00343a009

Reference yield:

(R)-2-tert-Butoxycarbonylamino-3-(4-ethoxy-phenyl)-propionic acid methyl ester (92507-32-9) → (R)-2-((tert-butoxycarbonyl)amino)-3-(4-ethoxyphenyl)propanoic acid (76757-92-1,247088-44-4)

Guidance literature:

With sodium hydroxide; In methanol; water; for 0.5h; Yield given;

DOI:10.1021/jo00322a049

Reference yield:

di-tert-butyl dicarbonate (24424-99-5) → (R)-2-((tert-butoxycarbonyl)amino)-3-(4-ethoxyphenyl)propanoic acid (76757-92-1,247088-44-4)

Guidance literature:

Multi-step reaction with 3 steps

1: 1.) K₂CO₃ / 1.) H₂O, 10 min, 2.) t-BuOH, ether, 25 min

2: K₂CO₃, 18-crown-6 / benzene / 1.5 h / Heating

3: NaOH / methanol; H₂O / 0.5 h

With sodium hydroxide; 18-crown-6 ether; potassium carbonate; In methanol; water; benzene;

DOI:10.1021/jo00322a049

upstream raw materials:

ethyl bromide

N-(tert-butoxycarbonyl)-D-tyrosine

diethyl sulfate

(R)-2-tert-Butoxycarbonylamino-3-(4-ethoxy-phenyl)-propionic acid methyl ester

Downstream raw materials:

Cbz-D-Phe

(R)-N-[(S)-1-(4-cyano-benzylcarbamoyl)-2-phenyl-ethyl]-3-(4-ethoxy-phenyl)-2-methanesulfonylamino-propionamide

(S)-N-(4-aminomethyl-benzyl)-2-[(R)-3-(4-ethoxy-phenyl)-2-propionylamino-propionylamino]-3-phenyl-propionamide trifluoroacetate

[4-({(S)-2-[(R)-3-(4-ethoxy-phenyl)-2-propionylamino-propionylamino]-3-phenyl-propionylamino}-methyl)-benzyl]-carbamic acid tert-butyl ester

Refernces

• 1、 Manning,Olma,Klis,Kolodziejczyk,Seto,Sawyer. "Design of more potent antagonists of the antidiuretic responses to arginine-vasopressin". . p. 45 - 50. Retrieved 2007/10/02.