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

Base Information

• Chemical Name: 3-methoxy-2-[1-(toluene-4-sulfonyl)-1H-indol-3-yl]-9-triisopropylsilanyloxy-8,9-dihydro-cycloheptapyrazin-5-one
• CAS No.: 911677-76-4
• Molecular Formula: C₃₄H₄₁N₃O₅SSi
• Molecular Weight: 631.868
• Mol file: 911677-76-4.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

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

2-methoxy-3-[1-(toluene-4-sulfonyl)-1H-indol-3-yl]-5-triisopropylsilanyloxy-9-trimethylsilanyloxy-6,9-dihydro-5H-cycloheptapyrazine → 3-methoxy-2-[1-(toluene-4-sulfonyl)-1H-indol-3-yl]-9-triisopropylsilanyloxy-8,9-dihydro-cycloheptapyrazin-5-one (911677-76-4)

Guidance literature:

With lithium hexamethyldisilazane; In tetrahydrofuran; at -78 - -50 ℃;

DOI:10.1021/ol0617547

Reference yield:

1-(3-bromo-6-iodo-5-methoxy-pyrazin-2-yl)-hex-5-en-1-ol (911677-86-6) → 3-methoxy-2-[1-(toluene-4-sulfonyl)-1H-indol-3-yl]-9-triisopropylsilanyloxy-8,9-dihydro-cycloheptapyrazin-5-one (911677-76-4)

Guidance literature:

Multi-step reaction with 6 steps

1: 86 percent / imidazole / dimethylformamide / 16 h / 40 °C

2: 85 percent / LiCl; CuCl / Pd(PPh₃)4 / dimethylsulfoxide / 0.5 h / 20 °C

3: 82 percent / NaOAc / Pd(PPh₃)4 / dimethylformamide / 2 h / 150 °C

4: 80 percent / N-methylmorpholine-N-oxide; OsO₄; NaIO₄ / tetrahydrofuran; H₂O / 20 h / 20 °C

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

6: 917 mg / LiHMDS / tetrahydrofuran / -78 - -50 °C

With 1H-imidazole; sodium periodate; osmium(VIII) oxide; sodium acetate; 4-methylmorpholine N-oxide; copper(l) chloride; lithium chloride; lithium hexamethyldisilazane; palladium diacetate; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In tetrahydrofuran; water; dimethyl sulfoxide; N,N-dimethyl-formamide; acetonitrile; 2: Stille coupling reaction / 3: Heck reaction / 4: Saegusa oxidation / 5: Saegusa oxidation;

DOI:10.1021/ol0617547

Reference yield:

2-bromo-5-iodo-6-methoxy-3-(1-triisopropylsilanyloxy-hex-5-enyl)-pyrazine (911677-73-1) → 3-methoxy-2-[1-(toluene-4-sulfonyl)-1H-indol-3-yl]-9-triisopropylsilanyloxy-8,9-dihydro-cycloheptapyrazin-5-one (911677-76-4)

Guidance literature:

Multi-step reaction with 5 steps

1: 85 percent / LiCl; CuCl / Pd(PPh₃)4 / dimethylsulfoxide / 0.5 h / 20 °C

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

3: 80 percent / N-methylmorpholine-N-oxide; OsO₄; NaIO₄ / tetrahydrofuran; H₂O / 20 h / 20 °C

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

5: 917 mg / LiHMDS / tetrahydrofuran / -78 - -50 °C

With sodium periodate; osmium(VIII) oxide; sodium acetate; 4-methylmorpholine N-oxide; copper(l) chloride; lithium chloride; lithium hexamethyldisilazane; palladium diacetate; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In tetrahydrofuran; water; dimethyl sulfoxide; N,N-dimethyl-formamide; acetonitrile; 1: Stille coupling reaction / 2: Heck reaction / 3: Saegusa oxidation / 4: Saegusa oxidation;

DOI:10.1021/ol0617547

upstream raw materials:

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-6,7,8,9-tetrahydro-cycloheptapyrazin-5-one

2-methoxy-9-methylene-3-[1-(toluene-4-sulfonyl)-1H-indol-3-yl]-5-triisopropylsilanyloxy-6,7,8,9-tetrahydro-5H-cycloheptapyrazine

Downstream 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

{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

C₄₆H₅₆N₄O₈SSi

4-{3-methoxy-5-oxo-2-[1-(toluene-4-sulfonyl)-1H-indol-3-yl]-9-triisopropylsilanyloxy-8,9-dihydro-5H-cycloheptapyrazin-6-yl}-2,2-dimethyl-5-vinyl-oxazole-3-carboxylic acid tert-butyl ester