(1R,6R,11aS,13S,14aR)-6-[2-(4-aminophenyl)ethyl]-1,13-bis{[tert-butyl(dimethyl)silyl]-oxy}-1,6,7,8,9,11a,12,13,14,14a-decahydro-4H-cyclopenta[f]oxacyclotridecin-4-one

Base Information

• Chemical Name: (1R,6R,11aS,13S,14aR)-6-[2-(4-aminophenyl)ethyl]-1,13-bis{[tert-butyl(dimethyl)silyl]-oxy}-1,6,7,8,9,11a,12,13,14,14a-decahydro-4H-cyclopenta[f]oxacyclotridecin-4-one
• CAS No.: 1446488-91-0
• Molecular Formula: C₃₅H₅₉NO₄Si₂
• Molecular Weight: 614.029
• Mol file: 1446488-91-0.mol

Synonyms:(1R,6R,11aS,13S,14aR)-6-[2-(4-aminophenyl)ethyl]-1,13-bis{[tert-butyl(dimethyl)silyl]-oxy}-1,6,7,8,9,11a,12,13,14,14a-decahydro-4H-cyclopenta[f]oxacyclotridecin-4-one

Chemical Property of (1R,6R,11aS,13S,14aR)-6-[2-(4-aminophenyl)ethyl]-1,13-bis{[tert-butyl(dimethyl)silyl]-oxy}-1,6,7,8,9,11a,12,13,14,14a-decahydro-4H-cyclopenta[f]oxacyclotridecin-4-one

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (1R,6R,11aS,13S,14aR)-6-[2-(4-aminophenyl)ethyl]-1,13-bis{[tert-butyl(dimethyl)silyl]-oxy}-1,6,7,8,9,11a,12,13,14,14a-decahydro-4H-cyclopenta[f]oxacyclotridecin-4-one

There total 16 articles about (1R,6R,11aS,13S,14aR)-6-[2-(4-aminophenyl)ethyl]-1,13-bis{[tert-butyl(dimethyl)silyl]-oxy}-1,6,7,8,9,11a,12,13,14,14a-decahydro-4H-cyclopenta[f]oxacyclotridecin-4-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: 41.0%

(1R,6R,11aS,13S,14aR)-1,13-bis{[tert-butyl(dimethyl)silyl]oxy}-6-vinyl-1,6,7,8,9,11a,12,13,14,14a-decahydro-4H-cyclopenta[f]oxacyclotridecin-4-one (1446488-84-1) → (1R,6R,11aS,13S,14aR)-6-[2-(4-aminophenyl)ethyl]-1,13-bis{[tert-butyl(dimethyl)silyl]-oxy}-1,6,7,8,9,11a,12,13,14,14a-decahydro-4H-cyclopenta[f]oxacyclotridecin-4-one (1446488-91-0)

Guidance literature:

(1R,6R,11aS,13S,14aR)-1,13-bis{[tert-butyl(dimethyl)silyl]oxy}-6-vinyl-1,6,7,8,9,11a,12,13,14,14a-decahydro-4H-cyclopenta[f]oxacyclotridecin-4-one; With 9-bora-bicyclo[3.3.1]nonane; In tetrahydrofuran; at 70 ℃; for 0.0833333h; Inert atmosphere;

4-amino-phenyl halide; With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; triphenyl-arsane; caesium carbonate; In tetrahydrofuran; water; N,N-dimethyl-formamide; for 20h; Inert atmosphere;

DOI:10.1021/jm400615g

Reference yield:

(1R,2E,6S,10E,11aS,13S,14aR)-1,13-bis[(tert-butyldimethylsilyl)oxy]-6-methyl-1,6,7,8,9,11a,12,13,14,14a-decahydro-4H-cyclopenta[f][1]oxacyclotridecin-4-one (177960-81-5) → (1R,6R,11aS,13S,14aR)-6-[2-(4-aminophenyl)ethyl]-1,13-bis{[tert-butyl(dimethyl)silyl]-oxy}-1,6,7,8,9,11a,12,13,14,14a-decahydro-4H-cyclopenta[f]oxacyclotridecin-4-one (1446488-91-0)

Guidance literature:

Multi-step reaction with 7 steps

1.1: potassium hydroxide / methanol; water / 0.5 h / 40 °C

1.2: 20 °C

2.1: potassium osmate(VI) dihydrate; 4-methylmorpholine N-oxide / water; acetone / 3 h / 20 °C

3.1: sodium periodate / water; tetrahydrofuran / 2 h / 20 °C

4.1: potassium hexamethylsilazane / toluene; 1,2-dimethoxyethane / 18 h / -78 - 20 °C

5.1: potassium hydrogencarbonate; palladium di-μ-chlorobis (η-allyl) / water; N,N-dimethyl-formamide / 3 h / 20 °C

6.1: methanol; sodium hydroxide / tetrahydrofuran / 1 h / 60 °C

7.1: 9-bora-bicyclo[3.3.1]nonane / tetrahydrofuran / 0.08 h / 70 °C / Inert atmosphere

7.2: 20 h / Inert atmosphere

With methanol; potassium osmate(VI) dihydrate; sodium periodate; palladium di-μ-chlorobis (η-allyl); potassium hexamethylsilazane; potassium hydrogencarbonate; 4-methylmorpholine N-oxide; 9-bora-bicyclo[3.3.1]nonane; potassium hydroxide; sodium hydroxide; In tetrahydrofuran; methanol; 1,2-dimethoxyethane; water; N,N-dimethyl-formamide; acetone; toluene; 7.1: |Suzuki-Miyaura Coupling / 7.2: |Suzuki-Miyaura Coupling;

DOI:10.1021/jm400615g

Reference yield:

ethyl (2E)-7-[(1-Phenyl-1H-tetrazol-5-yl)thio]hept-2-enoate (1446488-81-8) → (1R,6R,11aS,13S,14aR)-6-[2-(4-aminophenyl)ethyl]-1,13-bis{[tert-butyl(dimethyl)silyl]-oxy}-1,6,7,8,9,11a,12,13,14,14a-decahydro-4H-cyclopenta[f]oxacyclotridecin-4-one (1446488-91-0)

Guidance literature:

Multi-step reaction with 7 steps

1.1: diisobutylaluminium hydride / tetrahydrofuran; hexane / -78 °C

2.1: pyridine / dichloromethane / 1 h / 0 - 20 °C / Inert atmosphere

3.1: dihydrogen peroxide; hexaammonium heptamolybdate tetrahydrate / ethanol / 16 h / 0 - 20 °C

4.1: potassium hexamethylsilazane / toluene; 1,2-dimethoxyethane / 18 h / -78 - 20 °C

5.1: potassium hydrogencarbonate; palladium di-μ-chlorobis (η-allyl) / water; N,N-dimethyl-formamide / 3 h / 20 °C

6.1: methanol; sodium hydroxide / tetrahydrofuran / 1 h / 60 °C

7.1: 9-bora-bicyclo[3.3.1]nonane / tetrahydrofuran / 0.08 h / 70 °C / Inert atmosphere

7.2: 20 h / Inert atmosphere

With pyridine; methanol; hexaammonium heptamolybdate tetrahydrate; palladium di-μ-chlorobis (η-allyl); dihydrogen peroxide; potassium hexamethylsilazane; diisobutylaluminium hydride; potassium hydrogencarbonate; 9-bora-bicyclo[3.3.1]nonane; sodium hydroxide; In tetrahydrofuran; 1,2-dimethoxyethane; ethanol; hexane; dichloromethane; water; N,N-dimethyl-formamide; toluene; 7.1: |Suzuki-Miyaura Coupling / 7.2: |Suzuki-Miyaura Coupling;

DOI:10.1021/jm400615g

upstream raw materials:

(1R,2E,6S,10E,11aS,13S,14aR)-1,13-bis[(tert-butyldimethylsilyl)oxy]-6-methyl-1,6,7,8,9,11a,12,13,14,14a-decahydro-4H-cyclopenta[f][1]oxacyclotridecin-4-one

methyl (2E,4R)-4-[(tert-butyldimethylsilyl)oxy]-4-{(1'R,2'S,4'S)-4'-[(tert-butyldimethylsilyl)oxy]-2'-[(1''E,6''S)-6''-hydroxyhept-1''-en-1''-yl]cyclopentyl}but-2-enoate

methyl (2E,4R)-4-{[tert-butyl(dimethyl)silyl]oxy}-4-((1R,2R,4R)-4-{[tert-butyl(dimethyl)-silyl]oxy}-2-formylcyclopentyl)but-2-enoate

ethyl (2E)-7-[(1-Phenyl-1H-tetrazol-5-yl)thio]hept-2-enoate

Downstream raw materials:

(1R,6R,11aS,13S,14aR)-1,13-dihydroxy-6-(2-quinolin-6-ylethyl)-1,6,7,8,9,11a,12,13,14,14a-decahydro-4H-cyclopenta[f]oxacyclotridecin-4-one