Benzoic acid (1S,2S,3S,4R,8S,9S,11R,12S)-8-(tert-butyl-dimethyl-silanyloxy)-1,2,11-trihydroxy-9,15,15-trimethyl-5-methylene-10-oxo-tricyclo[10.2.1.0^4,9]pentadec-3-yl ester

Base Information

• Chemical Name: Benzoic acid (1S,2S,3S,4R,8S,9S,11R,12S)-8-(tert-butyl-dimethyl-silanyloxy)-1,2,11-trihydroxy-9,15,15-trimethyl-5-methylene-10-oxo-tricyclo[10.2.1.0^4,9]pentadec-3-yl ester
• CAS No.: 832724-48-8
• Molecular Formula: C₃₂H₄₈O₇Si
• Molecular Weight: 572.814

Synonyms:Benzoic acid (1S,2S,3S,4R,8S,9S,11R,12S)-8-(tert-butyl-dimethyl-silanyloxy)-1,2,11-trihydroxy-9,15,15-trimethyl-5-methylene-10-oxo-tricyclo[10.2.1.0^4,9]pentadec-3-yl ester

Chemical Property of Benzoic acid (1S,2S,3S,4R,8S,9S,11R,12S)-8-(tert-butyl-dimethyl-silanyloxy)-1,2,11-trihydroxy-9,15,15-trimethyl-5-methylene-10-oxo-tricyclo[10.2.1.0^4,9]pentadec-3-yl ester

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Technology Process of Benzoic acid (1S,2S,3S,4R,8S,9S,11R,12S)-8-(tert-butyl-dimethyl-silanyloxy)-1,2,11-trihydroxy-9,15,15-trimethyl-5-methylene-10-oxo-tricyclo[10.2.1.0^4,9]pentadec-3-yl ester

There total 5 articles about Benzoic acid (1S,2S,3S,4R,8S,9S,11R,12S)-8-(tert-butyl-dimethyl-silanyloxy)-1,2,11-trihydroxy-9,15,15-trimethyl-5-methylene-10-oxo-tricyclo[10.2.1.0^4,9]pentadec-3-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: 74.0%

C40H54O8Si (832724-47-7) → Benzoic acid (1S,2S,3S,4R,8S,9S,11R,12S)-8-(tert-butyl-dimethyl-silanyloxy)-1,2,11-trihydroxy-9,15,15-trimethyl-5-methylene-10-oxo-tricyclo[10.2.1.04,9]pentadec-3-yl ester (832724-48-8)

Guidance literature:

With ethylaluminum dichloride; In hexane; dichloromethane; at -78 - 20 ℃; for 0.333333h;

DOI:10.1021/jo048289g

Reference yield:

benzoyl chloride (98-88-4) → Benzoic acid (1S,2S,3S,4R,8S,9S,11R,12S)-8-(tert-butyl-dimethyl-silanyloxy)-1,2,11-trihydroxy-9,15,15-trimethyl-5-methylene-10-oxo-tricyclo[10.2.1.04,9]pentadec-3-yl ester (832724-48-8)

Guidance literature:

Multi-step reaction with 2 steps

1: 89 percent / pyridine; DMAP / 19 h / 20 °C

2: 74 percent / ethylaluminum dichloride / CH₂Cl₂; hexane / 0.33 h / -78 - 20 °C

With pyridine; dmap; ethylaluminum dichloride; In hexane; dichloromethane;

DOI:10.1021/jo048289g

Reference yield:

(1S,4R,8S,9R,10R,11R,12S)-8-(tert-Butyl-dimethyl-silanyloxy)-1,10-dihydroxy-11-(4-methoxy-benzyloxy)-9,15,15-trimethyl-5-methylene-tricyclo[10.2.1.04,9]pentadecan-2-one (350715-47-8) → Benzoic acid (1S,2S,3S,4R,8S,9S,11R,12S)-8-(tert-butyl-dimethyl-silanyloxy)-1,2,11-trihydroxy-9,15,15-trimethyl-5-methylene-10-oxo-tricyclo[10.2.1.04,9]pentadec-3-yl ester (832724-48-8)

Guidance literature:

Multi-step reaction with 4 steps

1.1: 75 percent / DDQ / CH₂Cl₂ / 24 h

2.1: KHMDS / tetrahydrofuran; toluene / 0.17 h / -78 °C

2.2: 95 percent / 3-phenyl-2-(phenylsulfonyl)oxaziridine / tetrahydrofuran; toluene / 2 h / -78 - 20 °C

3.1: 89 percent / pyridine; DMAP / 19 h / 20 °C

4.1: 74 percent / ethylaluminum dichloride / CH₂Cl₂; hexane / 0.33 h / -78 - 20 °C

With pyridine; dmap; ethylaluminum dichloride; potassium hexamethylsilazane; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In tetrahydrofuran; hexane; dichloromethane; toluene;

DOI:10.1021/jo048289g

upstream raw materials:

C₄₀H₅₄O₈Si

benzoyl chloride

(1S,4R,8S,9R,10R,11R,12S)-8-(tert-Butyl-dimethyl-silanyloxy)-1,10-dihydroxy-11-(4-methoxy-benzyloxy)-9,15,15-trimethyl-5-methylene-tricyclo[10.2.1.0^4,9]pentadecan-2-one

C₃₃H₅₀O₆Si

Downstream raw materials:

Benzoic acid (1S,2S,3S,4R,8S,9S,11R,12S)-8-(tert-butyl-dimethyl-silanyloxy)-1,11-dihydroxy-2-methanesulfonyloxy-9,15,15-trimethyl-5-methylene-10-oxo-tricyclo[10.2.1.0^4,9]pentadec-3-yl ester

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