(1S,3S,4R,8S,9S,11R,12S)-8-(tert-Butyl-dimethyl-silanyloxy)-1,3-dihydroxy-11-(4-methoxy-benzyloxy)-9,15,15-trimethyl-5-methylene-tricyclo[10.2.1.0^4,9]pentadecane-2,10-dione

Base Information

• Chemical Name: (1S,3S,4R,8S,9S,11R,12S)-8-(tert-Butyl-dimethyl-silanyloxy)-1,3-dihydroxy-11-(4-methoxy-benzyloxy)-9,15,15-trimethyl-5-methylene-tricyclo[10.2.1.0^4,9]pentadecane-2,10-dione
• CAS No.: 512828-35-2
• Molecular Formula: C₃₃H₅₀O₇Si
• Molecular Weight: 586.841
• Mol file: 512828-35-2.mol

Synonyms:(1S,3S,4R,8S,9S,11R,12S)-8-(tert-Butyl-dimethyl-silanyloxy)-1,3-dihydroxy-11-(4-methoxy-benzyloxy)-9,15,15-trimethyl-5-methylene-tricyclo[10.2.1.0^4,9]pentadecane-2,10-dione

Chemical Property of (1S,3S,4R,8S,9S,11R,12S)-8-(tert-Butyl-dimethyl-silanyloxy)-1,3-dihydroxy-11-(4-methoxy-benzyloxy)-9,15,15-trimethyl-5-methylene-tricyclo[10.2.1.0^4,9]pentadecane-2,10-dione

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (1S,3S,4R,8S,9S,11R,12S)-8-(tert-Butyl-dimethyl-silanyloxy)-1,3-dihydroxy-11-(4-methoxy-benzyloxy)-9,15,15-trimethyl-5-methylene-tricyclo[10.2.1.0^4,9]pentadecane-2,10-dione

There total 2 articles about (1S,3S,4R,8S,9S,11R,12S)-8-(tert-Butyl-dimethyl-silanyloxy)-1,3-dihydroxy-11-(4-methoxy-benzyloxy)-9,15,15-trimethyl-5-methylene-tricyclo[10.2.1.0^4,9]pentadecane-2,10-dione 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: 98.0%

(1S,4R,8S,9S,11R,12S)-8-(tert-Butyl-dimethyl-silanyloxy)-1-hydroxy-11-(4-methoxy-benzyloxy)-9,15,15-trimethyl-5-methylene-tricyclo[10.2.1.04,9]pentadecane-2,10-dione (512828-34-1) → (1S,3S,4R,8S,9S,11R,12S)-8-(tert-Butyl-dimethyl-silanyloxy)-1,3-dihydroxy-11-(4-methoxy-benzyloxy)-9,15,15-trimethyl-5-methylene-tricyclo[10.2.1.04,9]pentadecane-2,10-dione (512828-35-2)

Guidance literature:

With PhSO₂-N(O)CH-Ph; potassium hexamethylsilazane; In tetrahydrofuran; toluene; at -78 - 10 ℃; for 2h;

DOI:10.1021/jo020628n

Reference yield:

(1S,2R,4S,5S,9R,11S,12S)-5-(tert-Butyl-dimethyl-silanyloxy)-11,12-dihydroxy-2-(4-methoxy-benzyloxy)-4,15,15-trimethyl-8-methylene-tricyclo[10.2.1.04,9]pentadecan-3-one (350715-45-6) → (1S,3S,4R,8S,9S,11R,12S)-8-(tert-Butyl-dimethyl-silanyloxy)-1,3-dihydroxy-11-(4-methoxy-benzyloxy)-9,15,15-trimethyl-5-methylene-tricyclo[10.2.1.04,9]pentadecane-2,10-dione (512828-35-2)

Guidance literature:

Multi-step reaction with 2 steps

1: 100 percent / oxalyl chloride; DMSO; Et₃N / CH₂Cl₂ / 5.5 h / -78 - 20 °C

2: 98 percent / potassium hexamethyldisilazide; PhSO₂N(O)CHPh / tetrahydrofuran; toluene / 2 h / -78 - 10 °C

With oxalyl dichloride; PhSO₂-N(O)CH-Ph; potassium hexamethylsilazane; dimethyl sulfoxide; triethylamine; In tetrahydrofuran; dichloromethane; toluene; 1: Swern oxidation;

DOI:10.1021/jo020628n

Reference yield: 85.0%

benzoyl chloride (98-88-4) + (1S,3S,4R,8S,9S,11R,12S)-8-(tert-Butyl-dimethyl-silanyloxy)-1,3-dihydroxy-11-(4-methoxy-benzyloxy)-9,15,15-trimethyl-5-methylene-tricyclo[10.2.1.04,9]pentadecane-2,10-dione (512828-35-2) → Benzoic acid (1S,3S,4R,8S,9S,11R,12S)-8-(tert-butyl-dimethyl-silanyloxy)-1-hydroxy-11-(4-methoxy-benzyloxy)-9,15,15-trimethyl-5-methylene-2,10-dioxo-tricyclo[10.2.1.04,9]pentadec-3-yl ester

Guidance literature:

With pyridine; dmap; for 6h;

DOI:10.1021/jo020628n

upstream raw materials:

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

(1S,2R,4S,5S,9R,11S,12S)-5-(tert-Butyl-dimethyl-silanyloxy)-11,12-dihydroxy-2-(4-methoxy-benzyloxy)-4,15,15-trimethyl-8-methylene-tricyclo[10.2.1.0^4,9]pentadecan-3-one