Benzoic acid (1S,2S,3S,9S,13S)-13-(tert-butyl-dimethyl-silanyloxy)-1,9-dihydroxy-4-methoxy-12,15,15-trimethyl-tricyclo[9.3.1.0^3,8]pentadeca-4,7,11-trien-2-yl ester

Base Information

• Chemical Name: Benzoic acid (1S,2S,3S,9S,13S)-13-(tert-butyl-dimethyl-silanyloxy)-1,9-dihydroxy-4-methoxy-12,15,15-trimethyl-tricyclo[9.3.1.0^3,8]pentadeca-4,7,11-trien-2-yl ester
• CAS No.: 183139-09-5
• Molecular Formula: C₃₂H₄₆O₆Si
• Molecular Weight: 554.799

Synonyms:Benzoic acid (1S,2S,3S,9S,13S)-13-(tert-butyl-dimethyl-silanyloxy)-1,9-dihydroxy-4-methoxy-12,15,15-trimethyl-tricyclo[9.3.1.0^3,8]pentadeca-4,7,11-trien-2-yl ester

Chemical Property of Benzoic acid (1S,2S,3S,9S,13S)-13-(tert-butyl-dimethyl-silanyloxy)-1,9-dihydroxy-4-methoxy-12,15,15-trimethyl-tricyclo[9.3.1.0^3,8]pentadeca-4,7,11-trien-2-yl ester

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Technology Process of Benzoic acid (1S,2S,3S,9S,13S)-13-(tert-butyl-dimethyl-silanyloxy)-1,9-dihydroxy-4-methoxy-12,15,15-trimethyl-tricyclo[9.3.1.0^3,8]pentadeca-4,7,11-trien-2-yl ester

There total 4 articles about Benzoic acid (1S,2S,3S,9S,13S)-13-(tert-butyl-dimethyl-silanyloxy)-1,9-dihydroxy-4-methoxy-12,15,15-trimethyl-tricyclo[9.3.1.0^3,8]pentadeca-4,7,11-trien-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: 68.0%

phenyllithium (591-51-5) + C26H40O6Si (183139-08-4) → Benzoic acid (1S,2S,3S,9S,13S)-13-(tert-butyl-dimethyl-silanyloxy)-1,9-dihydroxy-4-methoxy-12,15,15-trimethyl-tricyclo[9.3.1.03,8]pentadeca-4,7,11-trien-2-yl ester (183139-09-5)

Guidance literature:

In tetrahydrofuran; at -78 ℃;

DOI:10.1021/jo961289z

Reference yield:

(1S,3R,9S,13S)-13-(tert-Butyl-dimethyl-silanyloxy)-1-hydroxy-4-methoxy-12,15,15-trimethyl-9-trimethylsilanyloxy-tricyclo[9.3.1.03,8]pentadeca-4,7,11-trien-2-one (183139-16-4) → Benzoic acid (1S,2S,3S,9S,13S)-13-(tert-butyl-dimethyl-silanyloxy)-1,9-dihydroxy-4-methoxy-12,15,15-trimethyl-tricyclo[9.3.1.03,8]pentadeca-4,7,11-trien-2-yl ester (183139-09-5)

Guidance literature:

Multi-step reaction with 4 steps

1: 69 percent / AcOH / methanol

2: 85 percent / Na, NH₃ / tetrahydrofuran / -78 °C

3: 99 percent / CH₂Cl₂; pyridine

4: 68 percent / tetrahydrofuran / -78 °C

With ammonia; sodium; acetic acid; In tetrahydrofuran; pyridine; methanol; dichloromethane;

DOI:10.1021/jo961289z

Reference yield:

(1S,3R,9S,13S)-13-(tert-Butyl-dimethyl-silanyloxy)-1,9-dihydroxy-4-methoxy-12,15,15-trimethyl-tricyclo[9.3.1.03,8]pentadeca-4,7,11-trien-2-one (183255-06-3) → Benzoic acid (1S,2S,3S,9S,13S)-13-(tert-butyl-dimethyl-silanyloxy)-1,9-dihydroxy-4-methoxy-12,15,15-trimethyl-tricyclo[9.3.1.03,8]pentadeca-4,7,11-trien-2-yl ester (183139-09-5)

Guidance literature:

Multi-step reaction with 3 steps

1: 85 percent / Na, NH₃ / tetrahydrofuran / -78 °C

2: 99 percent / CH₂Cl₂; pyridine

3: 68 percent / tetrahydrofuran / -78 °C

With ammonia; sodium; In tetrahydrofuran; pyridine; dichloromethane;

DOI:10.1021/jo961289z

upstream raw materials:

phenyllithium

C₂₆H₄₀O₆Si

(1S,2S,3S,9S,13S)-13-(tert-Butyl-dimethyl-silanyloxy)-4-methoxy-12,15,15-trimethyl-tricyclo[9.3.1.0^3,8]pentadeca-4,7,11-triene-1,2,9-triol

(1S,3R,9S,13S)-13-(tert-Butyl-dimethyl-silanyloxy)-1-hydroxy-4-methoxy-12,15,15-trimethyl-9-trimethylsilanyloxy-tricyclo[9.3.1.0^3,8]pentadeca-4,7,11-trien-2-one

Downstream raw materials:

Benzoic acid (1S,2S,3S,13S)-13-(tert-butyl-dimethyl-silanyloxy)-1-hydroxy-4-methoxy-12,15,15-trimethyl-9-oxo-tricyclo[9.3.1.0^3,8]pentadeca-4,7,11-trien-2-yl ester

C₃₃H₄₆O₆Si

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