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

Base Information

• Chemical Name: 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
• CAS No.: 832724-49-9
• Molecular Formula: C₃₃H₅₀O₉SSi
• Molecular Weight: 650.906

Synonyms: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

Chemical Property of 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

Chemical Property:

Purity/Quality:

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Technology Process of 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

There total 6 articles about 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 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: 54.0%

methanesulfonyl chloride (124-63-0) + 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) → 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[10.2.1.04,9]pentadec-3-yl ester (832724-49-9)

Guidance literature:

With dmap; triethylamine; In dichloromethane; at 0 ℃; 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)-1,11-dihydroxy-2-methanesulfonyloxy-9,15,15-trimethyl-5-methylene-10-oxo-tricyclo[10.2.1.04,9]pentadec-3-yl ester (832724-49-9)

Guidance literature:

Multi-step reaction with 3 steps

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

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

3: 54 percent / DMAP; triethylamine / CH₂Cl₂ / 0.33 h / 0 °C

With pyridine; dmap; ethylaluminum dichloride; triethylamine; 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)-1,11-dihydroxy-2-methanesulfonyloxy-9,15,15-trimethyl-5-methylene-10-oxo-tricyclo[10.2.1.04,9]pentadec-3-yl ester (832724-49-9)

Guidance literature:

Multi-step reaction with 5 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

5.1: 54 percent / DMAP; triethylamine / CH₂Cl₂ / 0.33 h / 0 °C

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

DOI:10.1021/jo048289g

upstream raw materials:

methanesulfonyl chloride

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

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

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