{7-benzyloxy-3-methoxy-5-oxo-2-[1-(toluene-4-sulfonyl)-1H-indol-3-yl]-11-triisopropylsilanyloxy-10,11-dihydro-5H-benzo[4,5]cyclohepta[1,2-b]pyrazin-6-ylamino}-acetic acid

Base Information

• Chemical Name: {7-benzyloxy-3-methoxy-5-oxo-2-[1-(toluene-4-sulfonyl)-1H-indol-3-yl]-11-triisopropylsilanyloxy-10,11-dihydro-5H-benzo[4,5]cyclohepta[1,2-b]pyrazin-6-ylamino}-acetic acid
• CAS No.: 911677-84-4
• Molecular Formula: C₄₇H₅₂N₄O₈SSi
• Molecular Weight: 861.103
• Mol file: 911677-84-4.mol

Synonyms:{7-benzyloxy-3-methoxy-5-oxo-2-[1-(toluene-4-sulfonyl)-1H-indol-3-yl]-11-triisopropylsilanyloxy-10,11-dihydro-5H-benzo[4,5]cyclohepta[1,2-b]pyrazin-6-ylamino}-acetic acid

Chemical Property of {7-benzyloxy-3-methoxy-5-oxo-2-[1-(toluene-4-sulfonyl)-1H-indol-3-yl]-11-triisopropylsilanyloxy-10,11-dihydro-5H-benzo[4,5]cyclohepta[1,2-b]pyrazin-6-ylamino}-acetic acid

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of {7-benzyloxy-3-methoxy-5-oxo-2-[1-(toluene-4-sulfonyl)-1H-indol-3-yl]-11-triisopropylsilanyloxy-10,11-dihydro-5H-benzo[4,5]cyclohepta[1,2-b]pyrazin-6-ylamino}-acetic acid

There total 14 articles about {7-benzyloxy-3-methoxy-5-oxo-2-[1-(toluene-4-sulfonyl)-1H-indol-3-yl]-11-triisopropylsilanyloxy-10,11-dihydro-5H-benzo[4,5]cyclohepta[1,2-b]pyrazin-6-ylamino}-acetic acid 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: 69.0%

{7-benzyloxy-3-methoxy-5-oxo-2-[1-(toluene-4-sulfonyl)-1H-indol-3-yl]-11-triisopropylsilanyloxy-10,11-dihydro-5H-benzo[4,5]cyclohepta[1,2-b]pyrazin-6-ylamino}-acetic acid methyl ester (911677-89-9) → {7-benzyloxy-3-methoxy-5-oxo-2-[1-(toluene-4-sulfonyl)-1H-indol-3-yl]-11-triisopropylsilanyloxy-10,11-dihydro-5H-benzo[4,5]cyclohepta[1,2-b]pyrazin-6-ylamino}-acetic acid (911677-84-4)

Guidance literature:

With lithium hydroxide; In tetrahydrofuran; water; at 0 ℃; for 2h;

DOI:10.1021/ol0617547

Reference yield:

1-(3-bromo-6-iodo-5-methoxy-pyrazin-2-yl)-hex-5-en-1-ol (911677-86-6) → {7-benzyloxy-3-methoxy-5-oxo-2-[1-(toluene-4-sulfonyl)-1H-indol-3-yl]-11-triisopropylsilanyloxy-10,11-dihydro-5H-benzo[4,5]cyclohepta[1,2-b]pyrazin-6-ylamino}-acetic acid (911677-84-4)

Guidance literature:

Multi-step reaction with 13 steps

1.1: 86 percent / imidazole / dimethylformamide / 16 h / 40 °C

2.1: 85 percent / LiCl; CuCl / Pd(PPh₃)4 / dimethylsulfoxide / 0.5 h / 20 °C

3.1: 82 percent / NaOAc / Pd(PPh₃)4 / dimethylformamide / 2 h / 150 °C

4.1: 80 percent / N-methylmorpholine-N-oxide; OsO₄; NaIO₄ / tetrahydrofuran; H₂O / 20 h / 20 °C

5.1: Pd(OAc)2 / acetonitrile / 20 h / 20 °C

6.1: 917 mg / LiHMDS / tetrahydrofuran / -78 - -50 °C

7.1: 86 percent / iodine / CCl₄; pyridine / 24 h / 20 °C

8.1: 71 percent / LiCl; CuCl / Pd(PPh₃)4 / dimethylsulfoxide / 0.5 h / 20 °C

9.1: toluene-d8 / 2 h / 110 °C

9.2: 72 percent / DDQ / 2 h / 20 °C

10.1: 69 percent / 2,6-lutidine; TMSTOf; aq. HCl / CH₂Cl₂; tetrahydrofuran / 2 h

11.1: 97 percent / NaH / dimethylformamide; various solvent(s) / 0.5 h

12.1: 62 percent / K₂CO₃ / dimethylformamide / 20 - 90 °C

13.1: 69 percent / LiOH / tetrahydrofuran; H₂O / 2 h / 0 °C

With 1H-imidazole; 2,6-dimethylpyridine; hydrogenchloride; lithium hydroxide; sodium periodate; osmium(VIII) oxide; trimethylsilyl trifluoromethanesulfonate; iodine; sodium acetate; sodium hydride; potassium carbonate; 4-methylmorpholine N-oxide; copper(l) chloride; lithium chloride; lithium hexamethyldisilazane; palladium diacetate; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In tetrahydrofuran; pyridine; tetrachloromethane; dichloromethane; ⁽²⁾H₈-toluene; water; dimethyl sulfoxide; N,N-dimethyl-formamide; acetonitrile; 2.1: Stille coupling reaction / 3.1: Heck reaction / 4.1: Saegusa oxidation / 5.1: Saegusa oxidation / 8.1: Stille coupling reaction;

DOI:10.1021/ol0617547

Reference yield:

2-bromo-5-iodo-6-methoxy-3-(1-triisopropylsilanyloxy-hex-5-enyl)-pyrazine (911677-73-1) → {7-benzyloxy-3-methoxy-5-oxo-2-[1-(toluene-4-sulfonyl)-1H-indol-3-yl]-11-triisopropylsilanyloxy-10,11-dihydro-5H-benzo[4,5]cyclohepta[1,2-b]pyrazin-6-ylamino}-acetic acid (911677-84-4)

Guidance literature:

Multi-step reaction with 12 steps

1.1: 85 percent / LiCl; CuCl / Pd(PPh₃)4 / dimethylsulfoxide / 0.5 h / 20 °C

2.1: 82 percent / NaOAc / Pd(PPh₃)4 / dimethylformamide / 2 h / 150 °C

3.1: 80 percent / N-methylmorpholine-N-oxide; OsO₄; NaIO₄ / tetrahydrofuran; H₂O / 20 h / 20 °C

4.1: Pd(OAc)2 / acetonitrile / 20 h / 20 °C

5.1: 917 mg / LiHMDS / tetrahydrofuran / -78 - -50 °C

6.1: 86 percent / iodine / CCl₄; pyridine / 24 h / 20 °C

7.1: 71 percent / LiCl; CuCl / Pd(PPh₃)4 / dimethylsulfoxide / 0.5 h / 20 °C

8.1: toluene-d8 / 2 h / 110 °C

8.2: 72 percent / DDQ / 2 h / 20 °C

9.1: 69 percent / 2,6-lutidine; TMSTOf; aq. HCl / CH₂Cl₂; tetrahydrofuran / 2 h

10.1: 97 percent / NaH / dimethylformamide; various solvent(s) / 0.5 h

11.1: 62 percent / K₂CO₃ / dimethylformamide / 20 - 90 °C

12.1: 69 percent / LiOH / tetrahydrofuran; H₂O / 2 h / 0 °C

With 2,6-dimethylpyridine; hydrogenchloride; lithium hydroxide; sodium periodate; osmium(VIII) oxide; trimethylsilyl trifluoromethanesulfonate; iodine; sodium acetate; sodium hydride; potassium carbonate; 4-methylmorpholine N-oxide; copper(l) chloride; lithium chloride; lithium hexamethyldisilazane; palladium diacetate; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In tetrahydrofuran; pyridine; tetrachloromethane; dichloromethane; ⁽²⁾H₈-toluene; water; dimethyl sulfoxide; N,N-dimethyl-formamide; acetonitrile; 1.1: Stille coupling reaction / 2.1: Heck reaction / 3.1: Saegusa oxidation / 4.1: Saegusa oxidation / 7.1: Stille coupling reaction;

DOI:10.1021/ol0617547

upstream raw materials:

{7-benzyloxy-3-methoxy-5-oxo-2-[1-(toluene-4-sulfonyl)-1H-indol-3-yl]-11-triisopropylsilanyloxy-10,11-dihydro-5H-benzo[4,5]cyclohepta[1,2-b]pyrazin-6-ylamino}-acetic acid methyl ester

1-(3-bromo-6-iodo-5-methoxy-pyrazin-2-yl)-hex-5-en-1-ol

2-bromo-5-iodo-6-methoxy-3-(1-triisopropylsilanyloxy-hex-5-enyl)-pyrazine

3-methoxy-2-[1-(toluene-4-sulfonyl)-1H-indol-3-yl]-9-triisopropylsilanyloxy-8,9-dihydro-cycloheptapyrazin-5-one