(9S,12S)-12-[N-(tert-butyloxycarbonyl)-N-methylamino]-2,11-dioxo-4-methoxy-9-methoxycarbonyl-10-methyl-10-azatricyclo[12.2.2.1^3,7]nonadeca-3,5,7⁽¹⁹⁾,14,16,17-hexaene

Base Information

• Chemical Name: (9S,12S)-12-[N-(tert-butyloxycarbonyl)-N-methylamino]-2,11-dioxo-4-methoxy-9-methoxycarbonyl-10-methyl-10-azatricyclo[12.2.2.1^3,7]nonadeca-3,5,7⁽¹⁹⁾,14,16,17-hexaene
• CAS No.: 138605-22-8
• Molecular Formula: C₂₇H₃₄N₂O₇
• Molecular Weight: 498.576
• Mol file: 138605-22-8.mol

Synonyms:(9S,12S)-12-[N-(tert-butyloxycarbonyl)-N-methylamino]-2,11-dioxo-4-methoxy-9-methoxycarbonyl-10-methyl-10-azatricyclo[12.2.2.1^3,7]nonadeca-3,5,7⁽¹⁹⁾,14,16,17-hexaene

Chemical Property of (9S,12S)-12-[N-(tert-butyloxycarbonyl)-N-methylamino]-2,11-dioxo-4-methoxy-9-methoxycarbonyl-10-methyl-10-azatricyclo[12.2.2.1^3,7]nonadeca-3,5,7⁽¹⁹⁾,14,16,17-hexaene

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (9S,12S)-12-[N-(tert-butyloxycarbonyl)-N-methylamino]-2,11-dioxo-4-methoxy-9-methoxycarbonyl-10-methyl-10-azatricyclo[12.2.2.1^3,7]nonadeca-3,5,7⁽¹⁹⁾,14,16,17-hexaene

There total 1 articles about (9S,12S)-12-[N-(tert-butyloxycarbonyl)-N-methylamino]-2,11-dioxo-4-methoxy-9-methoxycarbonyl-10-methyl-10-azatricyclo[12.2.2.1^3,7]nonadeca-3,5,7⁽¹⁹⁾,14,16,17-hexaene 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:

N-Boc-4-I-Phe-OH (103882-09-3,62129-44-6) → (9S,12S)-12-[N-(tert-butyloxycarbonyl)-N-methylamino]-2,11-dioxo-4-methoxy-9-methoxycarbonyl-10-methyl-10-azatricyclo[12.2.2.13,7]nonadeca-3,5,7(19),14,16,17-hexaene (138605-22-8)

Guidance literature:

Multi-step reaction with 3 steps

1: 85 percent / NaH / dimethylformamide / 6 h / 0 - 25 °C

2: EDCI, HOBt*H₂O / dimethylformamide / 16 h / 25 °C

3: 1.) NaH, CuBr, SMe₂ / 1.) collidine, 25 deg C, 0.5 h, 2.) collidine, 130 deg C, 9 h

With dimethylsulfide; sodium hydride; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; copper(I) bromide; In N,N-dimethyl-formamide;

DOI:10.1021/ja00062a004

Reference yield:

(9S,12S)-12-[N-(tert-butyloxycarbonyl)-N-methylamino]-2,11-dioxo-4-methoxy-9-methoxycarbonyl-10-methyl-10-azatricyclo[12.2.2.13,7]nonadeca-3,5,7(19),14,16,17-hexaene (138605-22-8) → RA-VII (122621-60-7,144993-87-3,144993-88-4,86229-97-2)

Guidance literature:

Multi-step reaction with 6 steps

1.1: 96 percent / trifluoroacetic acid / CH₂Cl₂ / 1 h / 20 °C

2.1: 97 percent / PyBrOP; diisopropylethylamine / dimethylformamide / 0 - 20 °C

3.1: trifluoroacetic acid / 0.33 h / 20 °C

3.2: 63 percent / diisopropylethylamine; 1-hydroxybenzotriazole; 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride / CH₂Cl₂ / 24 h / 20 °C

4.1: 82 percent / LiOH*H₂O / tetrahydrofuran; methanol; H₂O / 1 h / 20 °C

5.1: HCl / ethyl acetate / 1 h

6.1: 2.5 mg / NaHCO₃; diphenylphosphoryl azide / dimethylformamide / 72 h / 5 °C

With hydrogenchloride; lithium hydroxide; diphenylphosphoranyl azide; sodium hydrogencarbonate; N-ethyl-N,N-diisopropylamine; bromo-tris(1-pyrrolidinyl)phosphonium hexafluorophosphate; trifluoroacetic acid; In tetrahydrofuran; methanol; dichloromethane; water; ethyl acetate; N,N-dimethyl-formamide; 1.1: Hydrolysis / 2.1: coupling / 3.1: Hydrolysis / 3.2: coupling / 4.1: Hydrolysis / 5.1: Hydrolysis / 6.1: Cyclization;

DOI:10.1021/jo990432w

Reference yield:

(9S,12S)-12-[N-(tert-butyloxycarbonyl)-N-methylamino]-2,11-dioxo-4-methoxy-9-methoxycarbonyl-10-methyl-10-azatricyclo[12.2.2.13,7]nonadeca-3,5,7(19),14,16,17-hexaene (138605-22-8) → C46H60N6O12 (135226-91-4)

Guidance literature:

Multi-step reaction with 4 steps

1.1: 96 percent / trifluoroacetic acid / CH₂Cl₂ / 1 h / 20 °C

2.1: 97 percent / PyBrOP; diisopropylethylamine / dimethylformamide / 0 - 20 °C

3.1: trifluoroacetic acid / 0.33 h / 20 °C

3.2: 63 percent / diisopropylethylamine; 1-hydroxybenzotriazole; 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride / CH₂Cl₂ / 24 h / 20 °C

4.1: 82 percent / LiOH*H₂O / tetrahydrofuran; methanol; H₂O / 1 h / 20 °C

With lithium hydroxide; N-ethyl-N,N-diisopropylamine; bromo-tris(1-pyrrolidinyl)phosphonium hexafluorophosphate; trifluoroacetic acid; In tetrahydrofuran; methanol; dichloromethane; water; N,N-dimethyl-formamide; 1.1: Hydrolysis / 2.1: coupling / 3.1: Hydrolysis / 3.2: coupling / 4.1: Hydrolysis;

DOI:10.1021/jo990432w

upstream raw materials:

N-Boc-4-I-Phe-OH

Downstream raw materials:

RA-VII

C₄₁H₅₂N₆O₁₀

C₄₆H₆₀N₆O₁₂

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