(1S,3aS,6aS)-1-(tert-Butyl-dimethyl-silanyloxymethyl)-5,5-dimethyl-6a-[(E)-3-((R)-toluene-4-sulfinyl)-allyl]-hexahydro-pentalen-2-one

Base Information

• Chemical Name: (1S,3aS,6aS)-1-(tert-Butyl-dimethyl-silanyloxymethyl)-5,5-dimethyl-6a-[(E)-3-((R)-toluene-4-sulfinyl)-allyl]-hexahydro-pentalen-2-one
• CAS No.: 119582-24-0
• Molecular Formula: C₂₇H₄₂O₃SSi
• Molecular Weight: 474.78
• Mol file: 119582-24-0.mol

Synonyms:

Chemical Property of (1S,3aS,6aS)-1-(tert-Butyl-dimethyl-silanyloxymethyl)-5,5-dimethyl-6a-[(E)-3-((R)-toluene-4-sulfinyl)-allyl]-hexahydro-pentalen-2-one

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (1S,3aS,6aS)-1-(tert-Butyl-dimethyl-silanyloxymethyl)-5,5-dimethyl-6a-[(E)-3-((R)-toluene-4-sulfinyl)-allyl]-hexahydro-pentalen-2-one

There total 4 articles about (1S,3aS,6aS)-1-(tert-Butyl-dimethyl-silanyloxymethyl)-5,5-dimethyl-6a-[(E)-3-((R)-toluene-4-sulfinyl)-allyl]-hexahydro-pentalen-2-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:

4,4-dimethyl-hept-6-en-1-yne (102650-76-0) → (1S,3aS,6aS)-1-(tert-Butyl-dimethyl-silanyloxymethyl)-5,5-dimethyl-6a-[(E)-3-((R)-toluene-4-sulfinyl)-allyl]-hexahydro-pentalen-2-one (119582-24-0)

Guidance literature:

Multi-step reaction with 4 steps

1: 1) n-BuLi, 2) HMPA / 1) THF, -78 deg C, 1 h, 2) THF, -20 deg C for 10 min and 25 deg C for 1 h

2: 89 percent / Et₃N, DMAP / CH₂Cl₂ / 12 h / 25 °C

3: 65 percent / heptane / sealed tube under CO atmosphere; 1) 25 deg C for 24 h, 2) 80 deg C for 48 h

4: 1) LDA / 1) THF, -78 deg C, 1 h, 2) THF, -78 deg C, 10 min

With N,N,N,N,N,N-hexamethylphosphoric triamide; dmap; n-butyllithium; triethylamine; lithium diisopropyl amide; In n-heptane; dichloromethane;

DOI:10.1016/S0040-4039(00)96755-8

Reference yield:

tert-Butyl-(5,5-dimethyl-oct-7-en-2-ynyloxy)-dimethyl-silane (119582-23-9) → (1S,3aS,6aS)-1-(tert-Butyl-dimethyl-silanyloxymethyl)-5,5-dimethyl-6a-[(E)-3-((R)-toluene-4-sulfinyl)-allyl]-hexahydro-pentalen-2-one (119582-24-0)

Guidance literature:

Multi-step reaction with 2 steps

1: 65 percent / heptane / sealed tube under CO atmosphere; 1) 25 deg C for 24 h, 2) 80 deg C for 48 h

2: 1) LDA / 1) THF, -78 deg C, 1 h, 2) THF, -78 deg C, 10 min

With lithium diisopropyl amide; In n-heptane;

DOI:10.1016/S0040-4039(00)96755-8

Reference yield:

5,5-Dimethyl-oct-7-en-2-yn-1-ol (116440-76-7) → (1S,3aS,6aS)-1-(tert-Butyl-dimethyl-silanyloxymethyl)-5,5-dimethyl-6a-[(E)-3-((R)-toluene-4-sulfinyl)-allyl]-hexahydro-pentalen-2-one (119582-24-0)

Guidance literature:

Multi-step reaction with 3 steps

1: 89 percent / Et₃N, DMAP / CH₂Cl₂ / 12 h / 25 °C

2: 65 percent / heptane / sealed tube under CO atmosphere; 1) 25 deg C for 24 h, 2) 80 deg C for 48 h

3: 1) LDA / 1) THF, -78 deg C, 1 h, 2) THF, -78 deg C, 10 min

With dmap; triethylamine; lithium diisopropyl amide; In n-heptane; dichloromethane;

DOI:10.1016/S0040-4039(00)96755-8

upstream raw materials:

p-tolyl allyl sulfoxide

2-<(t-butyldimethylsilyloxy)methyl>-7,7-dimethylbicyclo<3.3.0>oct-2-en-3-one

4,4-dimethyl-hept-6-en-1-yne

tert-Butyl-(5,5-dimethyl-oct-7-en-2-ynyloxy)-dimethyl-silane

Downstream raw materials:

Acetic acid (1S,2S,3aS,6aS)-1-(tert-butyl-dimethyl-silanyloxymethyl)-5,5-dimethyl-6a-[(E)-3-((R)-toluene-4-sulfinyl)-allyl]-octahydro-pentalen-2-yl ester

Acetic acid (1R,2R,3aR,6aR)-1-(tert-butyl-dimethyl-silanyloxymethyl)-5,5-dimethyl-6a-((E)-3-p-tolylsulfanyl-allyl)-octahydro-pentalen-2-yl ester

(1S,2S,3aS,6aS)-1-(tert-Butyl-dimethyl-silanyloxymethyl)-5,5-dimethyl-6a-[(E)-3-((R)-toluene-4-sulfinyl)-allyl]-octahydro-pentalen-2-ol

(1S,2R,3aS,6aS)-1-(tert-Butyl-dimethyl-silanyloxymethyl)-5,5-dimethyl-6a-[(E)-3-((R)-toluene-4-sulfinyl)-allyl]-octahydro-pentalen-2-ol