BOC-D-alanyl-L-alanyl-N,O⁴-dimethyl-L-tyrosyl-L-alanyl-L-tyrosyl-N,O⁴-dimethyl-L-tyrosine cyclic 5⁴<*>6³ ether, methyl ester

Base Information

• Chemical Name: BOC-D-alanyl-L-alanyl-N,O⁴-dimethyl-L-tyrosyl-L-alanyl-L-tyrosyl-N,O⁴-dimethyl-L-tyrosine cyclic 5⁴<*>6³ ether, methyl ester
• CAS No.: 167316-09-8
• Molecular Formula: C₄₆H₆₀N₆O₁₂
• Molecular Weight: 889.015
• Mol file: 167316-09-8.mol

Synonyms:BOC-D-alanyl-L-alanyl-N,O⁴-dimethyl-L-tyrosyl-L-alanyl-L-tyrosyl-N,O⁴-dimethyl-L-tyrosine cyclic 5⁴<*>6³ ether, methyl ester

Chemical Property of BOC-D-alanyl-L-alanyl-N,O⁴-dimethyl-L-tyrosyl-L-alanyl-L-tyrosyl-N,O⁴-dimethyl-L-tyrosine cyclic 5⁴<*>6³ ether, methyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of BOC-D-alanyl-L-alanyl-N,O⁴-dimethyl-L-tyrosyl-L-alanyl-L-tyrosyl-N,O⁴-dimethyl-L-tyrosine cyclic 5⁴<*>6³ ether, methyl ester

There total 9 articles about BOC-D-alanyl-L-alanyl-N,O⁴-dimethyl-L-tyrosyl-L-alanyl-L-tyrosyl-N,O⁴-dimethyl-L-tyrosine cyclic 5⁴<*>6³ ether, 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: 87.0%

BOC-D-Ala-L-Ala-NMe-L-Tyr(OMe)-L-Ala-OC6F5 (112196-81-3) + methyl 12(S)-amino-4-methoxy-10-methyl-11-oxo-10-aza-2-oxatricyclo<12.2.2.2.13,7>nonadeca-3,5,7(19),14,16,17-hexaen-9(S)-carboxylate (167467-04-1) → BOC-D-alanyl-L-alanyl-N,O4-dimethyl-L-tyrosyl-L-alanyl-L-tyrosyl-N,O4-dimethyl-L-tyrosine cyclic 54<*>63 ether, methyl ester (167316-09-8)

Guidance literature:

In tetrahydrofuran; at 25 ℃; for 2h;

DOI:10.1021/ja00133a010

Reference yield:

(S)-3-(3-Acetoxy-4-methoxy-phenyl)-2-(benzyloxycarbonyl-methyl-amino)-propionic acid methyl ester (135226-83-4) → BOC-D-alanyl-L-alanyl-N,O4-dimethyl-L-tyrosyl-L-alanyl-L-tyrosyl-N,O4-dimethyl-L-tyrosine cyclic 54<*>63 ether, methyl ester (167316-09-8)

Guidance literature:

Multi-step reaction with 6 steps

1: 98 percent / H₂ / 10percent Pd/C / methanol / 3 h / 25 °C / 760 Torr

2: 84 percent / bis(2-oxo-3-oxazolidinyl)phosphinic chloride, triethylamine / CH₂Cl₂ / 12 h / 4 °C

3: 95 percent / aq. K₂CO₃ / tetrahydrofuran; methanol / 12 h / 25 °C

4: 1.) NaH, collidine, 2.) CuBr-SMe₂ / 1.) 0 deg C, 15 min, 2.) a) 25 deg C, 1 h, b) reflux, 10 h

5: 91 percent / HCl / ethyl acetate / 0.5 h / 25 °C

6: 87 percent / tetrahydrofuran / 2 h / 25 °C

With 2,3,5-trimethyl-pyridine; hydrogenchloride; hydrogen; bis-(2-oxo-3-oxazolidinyl)phosphoryl chloride; sodium hydride; potassium carbonate; triethylamine; palladium on activated charcoal; In tetrahydrofuran; methanol; dichloromethane; ethyl acetate;

DOI:10.1021/ja00133a010

Reference yield:

N,O4-dimethyl-L-DOPA methyl ester (135226-85-6) → BOC-D-alanyl-L-alanyl-N,O4-dimethyl-L-tyrosyl-L-alanyl-L-tyrosyl-N,O4-dimethyl-L-tyrosine cyclic 54<*>63 ether, methyl ester (167316-09-8)

Guidance literature:

Multi-step reaction with 4 steps

1: 78 percent / dimethylformamide / 24 h / 25 °C

2: 1.) NaH, collidine, 2.) CuBr-SMe₂ / 1.) 0 deg C, 15 min, 2.) a) 25 deg C, 1 h, b) reflux, 10 h

3: 91 percent / HCl / ethyl acetate / 0.5 h / 25 °C

4: 87 percent / tetrahydrofuran / 2 h / 25 °C

With 2,3,5-trimethyl-pyridine; hydrogenchloride; sodium hydride; In tetrahydrofuran; ethyl acetate; N,N-dimethyl-formamide;

DOI:10.1021/ja00133a010

upstream raw materials:

BOC-D-Ala-L-Ala-NMe-L-Tyr(OMe)-L-Ala-OC₆F₅

methyl 12(S)-amino-4-methoxy-10-methyl-11-oxo-10-aza-2-oxatricyclo<12.2.2.2.1^3,7>nonadeca-3,5,7(19),14,16,17-hexaen-9(S)-carboxylate

N,O⁴-dimethyl-L-DOPA methyl ester

(S)-3-(3-Acetoxy-4-methoxy-phenyl)-2-(benzyloxycarbonyl-methyl-amino)-propionic acid methyl ester

Downstream raw materials:

C₄₅H₅₈N₆O₁₂