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

Base Information

• Chemical Name: BOC-D-alanyl-L-alanyl-O⁴-methyl-L-tyrosyl-L-alanyl-N-methyl-L-tyrosyl-O⁴-methyl-L-tyrosine cyclic 5⁴<*>6³ ether, methyl ester
• CAS No.: 167316-11-2
• Molecular Formula: C₄₅H₅₈N₆O₁₂
• Molecular Weight: 874.989

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

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

Chemical Property:

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

There total 9 articles about BOC-D-alanyl-L-alanyl-O⁴-methyl-L-tyrosyl-L-alanyl-N-methyl-L-tyrosyl-O⁴-methyl-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: 83.0%

methyl 4-methoxy-12(S)--11-oxo-10-aza-2-oxatricyclo<12.2.2.13,7>-nonadeca-3,5,7(19),14,16,17-hexaene-9(R)-carboxylate (138571-39-8) + BOC-D-Ala-L-Ala-L-Tyr(OMe)-L-Ala-OC6F5 (161635-05-8) → BOC-D-alanyl-L-alanyl-O4-methyl-L-tyrosyl-L-alanyl-N-methyl-L-tyrosyl-O4-methyl-L-tyrosine cyclic 54<*>63 ether, methyl ester (167316-11-2)

Guidance literature:

In tetrahydrofuran; at 50 ℃; for 12h;

DOI:10.1021/ja00133a010

Reference yield:

O-Methyltyrosine (6230-11-1) → BOC-D-alanyl-L-alanyl-O4-methyl-L-tyrosyl-L-alanyl-N-methyl-L-tyrosyl-O4-methyl-L-tyrosine cyclic 54<*>63 ether, methyl ester (167316-11-2)

Guidance literature:

Multi-step reaction with 7 steps

1: 91 percent

2: 88 percent / 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride, 1-hydroxybenzotriazole, NaHCO₃ / dimethylformamide / 10 h / 25 °C

3: 85 percent / trifluoroacetic acid / CH₂Cl₂ / 1 h / 25 °C

4: 88 percent / EDCI, HOBt / dimethylformamide / 12 h / 25 °C

5: 90 percent / aq. LiOH / tetrahydrofuran; methanol / 3 h / 25 °C

6: 86 percent / EDCI / CH₂Cl₂ / 4 h / 25 °C

7: 83 percent / tetrahydrofuran / 12 h / 50 °C

With lithium hydroxide; sodium hydrogencarbonate; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; trifluoroacetic acid; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1021/ja00133a010

Reference yield:

O-methyl-N-tert-butoxycarbonyl-L-tyrosine (53267-93-9) → BOC-D-alanyl-L-alanyl-O4-methyl-L-tyrosyl-L-alanyl-N-methyl-L-tyrosyl-O4-methyl-L-tyrosine cyclic 54<*>63 ether, methyl ester (167316-11-2)

Guidance literature:

Multi-step reaction with 6 steps

1: 88 percent / 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride, 1-hydroxybenzotriazole, NaHCO₃ / dimethylformamide / 10 h / 25 °C

2: 85 percent / trifluoroacetic acid / CH₂Cl₂ / 1 h / 25 °C

3: 88 percent / EDCI, HOBt / dimethylformamide / 12 h / 25 °C

4: 90 percent / aq. LiOH / tetrahydrofuran; methanol / 3 h / 25 °C

5: 86 percent / EDCI / CH₂Cl₂ / 4 h / 25 °C

6: 83 percent / tetrahydrofuran / 12 h / 50 °C

With lithium hydroxide; sodium hydrogencarbonate; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; trifluoroacetic acid; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1021/ja00133a010

upstream raw materials:

methyl 4-methoxy-12(S)--11-oxo-10-aza-2-oxatricyclo<12.2.2.1^3,7>-nonadeca-3,5,7(19),14,16,17-hexaene-9(R)-carboxylate

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

O-Methyltyrosine

O-methyl-N-tert-butoxycarbonyl-L-tyrosine

Downstream raw materials:

C₄₄H₅₆N₆O₁₂

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