Benzoic acid (E)-(1R,2S,5S,7S,8S,10R,13S)-13-hydroxy-8,12,15,15-tetramethyl-9-oxo-5,7,10-tris-triethylsilanyloxy-tricyclo[9.3.1.1^4,8]hexadeca-3,11-dien-2-yl ester

Base Information

• Chemical Name: Benzoic acid (E)-(1R,2S,5S,7S,8S,10R,13S)-13-hydroxy-8,12,15,15-tetramethyl-9-oxo-5,7,10-tris-triethylsilanyloxy-tricyclo[9.3.1.1^4,8]hexadeca-3,11-dien-2-yl ester
• CAS No.: 204259-94-9
• Molecular Formula: C₄₅H₇₆O₇Si₃
• Molecular Weight: 813.351

Synonyms:Benzoic acid (E)-(1R,2S,5S,7S,8S,10R,13S)-13-hydroxy-8,12,15,15-tetramethyl-9-oxo-5,7,10-tris-triethylsilanyloxy-tricyclo[9.3.1.1^4,8]hexadeca-3,11-dien-2-yl ester

Chemical Property of Benzoic acid (E)-(1R,2S,5S,7S,8S,10R,13S)-13-hydroxy-8,12,15,15-tetramethyl-9-oxo-5,7,10-tris-triethylsilanyloxy-tricyclo[9.3.1.1^4,8]hexadeca-3,11-dien-2-yl ester

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Technology Process of Benzoic acid (E)-(1R,2S,5S,7S,8S,10R,13S)-13-hydroxy-8,12,15,15-tetramethyl-9-oxo-5,7,10-tris-triethylsilanyloxy-tricyclo[9.3.1.1^4,8]hexadeca-3,11-dien-2-yl ester

There total 5 articles about Benzoic acid (E)-(1R,2S,5S,7S,8S,10R,13S)-13-hydroxy-8,12,15,15-tetramethyl-9-oxo-5,7,10-tris-triethylsilanyloxy-tricyclo[9.3.1.1^4,8]hexadeca-3,11-dien-2-yl 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: 86.0%

benzoic acid (65-85-0,8013-63-6) + (E)-(1S,3R,6S,8R,9S,12S,14S)-6,9-Dihydroxy-1,5,16,16-tetramethyl-3,12,14-tris-triethylsilanyloxy-tricyclo[9.3.1.14,8]hexadeca-4,10-dien-2-one (204259-97-2) → Benzoic acid (E)-(1R,2S,5S,7S,8S,10R,13S)-13-hydroxy-8,12,15,15-tetramethyl-9-oxo-5,7,10-tris-triethylsilanyloxy-tricyclo[9.3.1.14,8]hexadeca-3,11-dien-2-yl ester (204259-94-9)

Guidance literature:

With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In N,N-dimethyl-formamide; for 20h; Ambient temperature;

DOI:10.1016/S0960-894X(98)00005-5

Reference yield:

triethylsilyl chloride (994-30-9) → Benzoic acid (E)-(1R,2S,5S,7S,8S,10R,13S)-13-hydroxy-8,12,15,15-tetramethyl-9-oxo-5,7,10-tris-triethylsilanyloxy-tricyclo[9.3.1.14,8]hexadeca-3,11-dien-2-yl ester (204259-94-9)

Guidance literature:

Multi-step reaction with 4 steps

1: 87 percent / pyridine / 18 h / Ambient temperature

2: 83 percent / AgNO₃, pyridine / 24 h / Ambient temperature

3: 95 percent / LiAlH₄ / tetrahydrofuran / 4 h / 0 °C

4: 86 percent / 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride, DMAP / dimethylformamide / 20 h / Ambient temperature

With pyridine; dmap; lithium aluminium tetrahydride; silver nitrate; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In tetrahydrofuran; N,N-dimethyl-formamide;

DOI:10.1016/S0960-894X(98)00005-5

Reference yield:

Acetic acid (E)-(1R,2S,5S,7S,8S,10S,13S)-13-acetoxy-5,7,10-trihydroxy-8,12,15,15-tetramethyl-9-oxo-tricyclo[9.3.1.14,8]hexadeca-3,11-dien-2-yl ester → Benzoic acid (E)-(1R,2S,5S,7S,8S,10R,13S)-13-hydroxy-8,12,15,15-tetramethyl-9-oxo-5,7,10-tris-triethylsilanyloxy-tricyclo[9.3.1.14,8]hexadeca-3,11-dien-2-yl ester (204259-94-9)

Guidance literature:

Multi-step reaction with 4 steps

1: 87 percent / pyridine / 18 h / Ambient temperature

2: 83 percent / AgNO₃, pyridine / 24 h / Ambient temperature

3: 95 percent / LiAlH₄ / tetrahydrofuran / 4 h / 0 °C

4: 86 percent / 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride, DMAP / dimethylformamide / 20 h / Ambient temperature

With pyridine; dmap; lithium aluminium tetrahydride; silver nitrate; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In tetrahydrofuran; N,N-dimethyl-formamide;

DOI:10.1016/S0960-894X(98)00005-5

upstream raw materials:

benzoic acid

(E)-(1S,3R,6S,8R,9S,12S,14S)-6,9-Dihydroxy-1,5,16,16-tetramethyl-3,12,14-tris-triethylsilanyloxy-tricyclo[9.3.1.1^4,8]hexadeca-4,10-dien-2-one

triethylsilyl chloride

Acetic acid (E)-(1R,2S,5S,7S,8S,10R,13S)-13-acetoxy-7,10-dihydroxy-8,12,15,15-tetramethyl-9-oxo-5-triethylsilanyloxy-tricyclo[9.3.1.1^4,8]hexadeca-3,11-dien-2-yl ester

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