(1S,2S,4R,9R)-4-[4-(tert-butyldiphenylsilyloxy)butyl]-9-hydroxy-4,8,11,11-tetramethyl-2-(phenylmethoxy)bicyclo[5.3.1]undec-7-en-3-one

Base Information

• Chemical Name: (1S,2S,4R,9R)-4-[4-(tert-butyldiphenylsilyloxy)butyl]-9-hydroxy-4,8,11,11-tetramethyl-2-(phenylmethoxy)bicyclo[5.3.1]undec-7-en-3-one
• CAS No.: 685077-49-0
• Molecular Formula: C₄₂H₅₆O₄Si
• Molecular Weight: 652.99
• Mol file: 685077-49-0.mol

Synonyms:(1S,2S,4R,9R)-4-[4-(tert-butyldiphenylsilyloxy)butyl]-9-hydroxy-4,8,11,11-tetramethyl-2-(phenylmethoxy)bicyclo[5.3.1]undec-7-en-3-one

Chemical Property of (1S,2S,4R,9R)-4-[4-(tert-butyldiphenylsilyloxy)butyl]-9-hydroxy-4,8,11,11-tetramethyl-2-(phenylmethoxy)bicyclo[5.3.1]undec-7-en-3-one

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (1S,2S,4R,9R)-4-[4-(tert-butyldiphenylsilyloxy)butyl]-9-hydroxy-4,8,11,11-tetramethyl-2-(phenylmethoxy)bicyclo[5.3.1]undec-7-en-3-one

There total 2 articles about (1S,2S,4R,9R)-4-[4-(tert-butyldiphenylsilyloxy)butyl]-9-hydroxy-4,8,11,11-tetramethyl-2-(phenylmethoxy)bicyclo[5.3.1]undec-7-en-3-one 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: 65.0%

(1R,3aR,7S,8S,8aR)-1-[4-(tert-butyldiphenylsilyloxy)butyl]-2,3,7,8-tetrahydro-1,4,9,9-tetramethyl-8-(phenylmethoxy)-1H-3a,7-methanoazulen-8a(6H)-ol (685077-48-9) → (1S,2S,4R,9R)-4-[4-(tert-butyldiphenylsilyloxy)butyl]-2,9-dihydroxy-4,8,11,11-tetramethylbicyclo[5.3.1]undec-7-en-3-one (685077-51-4) + (1S,2S,4R,9R)-4-[4-(tert-butyldiphenylsilyloxy)butyl]-9-hydroxy-4,8,11,11-tetramethyl-2-(phenylmethoxy)bicyclo[5.3.1]undec-7-en-3-one (685077-49-0) + (1S,2S,4R,9R)-4-[4-(tert-butyldiphenylsilyloxy)butyl]-9-hydroxy-4,8,11,11-tetramethyl-3-oxobicyclo[5.3.1]undec-7-en-2-yl benzoate

Guidance literature:

(1R,3aR,7S,8S,8aR)-1-[4-(tert-butyldiphenylsilyloxy)butyl]-2,3,7,8-tetrahydro-1,4,9,9-tetramethyl-8-(phenylmethoxy)-1H-3a,7-methanoazulen-8a(6H)-ol; With 3,3-dimethyldioxirane; potassium carbonate; In acetone; at 0 ℃; for 24h;

In toluene; for 2h; Heating;

DOI:10.1071/CH03161

Reference yield: 61.0%

(1R,3aR,7S,8S,8aR)-1-[4-(tert-butyldiphenylsilyloxy)butyl]-2,3,7,8-tetrahydro-1,4,9,9-tetramethyl-8-(phenylmethoxy)-1H-3a,7-methanoazulen-8a(6H)-ol (685077-48-9) → (1S,2S,4R,9R)-4-[4-(tert-butyldiphenylsilyloxy)butyl]-2,9-dihydroxy-4,8,11,11-tetramethylbicyclo[5.3.1]undec-7-en-3-one (685077-51-4) + (1S,2S,4R,9R)-4-[4-(tert-butyldiphenylsilyloxy)butyl]-9-hydroxy-4,8,11,11-tetramethyl-2-(phenylmethoxy)bicyclo[5.3.1]undec-7-en-3-one (685077-49-0)

Guidance literature:

With 3,3-dimethyldioxirane; potassium carbonate; In acetone; at -20 - 18 ℃;

DOI:10.1071/CH03161

Reference yield:

(1S,2S,4R,9R)-4-[4-(tert-butyldiphenylsilyloxy)butyl]-9-hydroxy-4,8,11,11-tetramethyl-2-(phenylmethoxy)bicyclo[5.3.1]undec-7-en-3-one (685077-49-0) → (1S,2S,4R)-4-(4-bromobutyl)-4,8,11,11-tetramethyl-2-(phenylmethoxy)bicyclo[5.3.1]undec-7-ene-3,9-dione (685077-57-0)

Guidance literature:

Multi-step reaction with 3 steps

1: 97 percent / 4-methylmorpholine N-oxide; tetrapropylammonium perruthenate; molecular sieves 4 Angstroem / CH₂Cl₂ / 3 h / 18 °C

2: 93 percent / tetrabutylammonium fluoride / tetrahydrofuran / 1 h / 18 °C

3: 96 percent / Ph₃P*Br₂ / CH₂Cl₂ / 1 h / 18 °C

With tetrapropylammonium perruthennate; 4 A molecular sieve; tetrabutyl ammonium fluoride; 4-methylmorpholine N-oxide; triphenylphosphine dibromide 1:1 addition complex; In tetrahydrofuran; dichloromethane;

DOI:10.1071/CH03161

upstream raw materials:

(1R,3aR,7S,8S,8aR)-1-[4-(tert-butyldiphenylsilyloxy)butyl]-2,3,7,8-tetrahydro-1,4,9,9-tetramethyl-8-(phenylmethoxy)-1H-3a,7-methanoazulen-8a(6H)-ol

Downstream raw materials:

(1S,2S,4R)-4-(4-bromobutyl)-4,8,11,11-tetramethyl-2-(phenylmethoxy)bicyclo[5.3.1]undec-7-ene-3,9-dione

(1S,2S,4R)-4-(4-hydroxybutyl)-4,8,11,11-tetramethyl-2-(phenylmethoxy)bicyclo[5.3.1]undec-7-ene-3,9-dione