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

Base Information

• Chemical Name: 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
• CAS No.: 119582-26-2
• Molecular Formula: C₂₉H₄₆O₄SSi
• Molecular Weight: 518.833
• Mol file: 119582-26-2.mol

Synonyms: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

Chemical Property of 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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 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

There total 6 articles about 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 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: 42.0%

(1S,2S,3aS,6aS)-1-(tert-Butyl-dimethyl-silanyloxymethyl)-5,5-dimethyl-6a-[(E)-3-((R)-toluene-4-sulfinyl)-allyl]-octahydro-pentalen-2-ol (119582-25-1,119618-32-5) + acetyl chloride (75-36-5) → 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 (119582-27-3) + 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 (119582-26-2)

Guidance literature:

With pyridine; In dichloromethane; at 0 ℃; for 2h;

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

Reference yield:

4,4-dimethyl-hept-6-en-1-yne (102650-76-0) → 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 (119582-26-2)

Guidance literature:

Multi-step reaction with 6 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

5: 92 percent / NaBH₄ / methanol / 2 h / -10 °C

6: 42 percent / pyridine / CH₂Cl₂ / 2 h / 0 °C

With pyridine; N,N,N,N,N,N-hexamethylphosphoric triamide; dmap; sodium tetrahydroborate; n-butyllithium; triethylamine; lithium diisopropyl amide; In methanol; 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) → 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 (119582-26-2)

Guidance literature:

Multi-step reaction with 4 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

3: 92 percent / NaBH₄ / methanol / 2 h / -10 °C

4: 42 percent / pyridine / CH₂Cl₂ / 2 h / 0 °C

With pyridine; sodium tetrahydroborate; lithium diisopropyl amide; In methanol; n-heptane; dichloromethane;

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

upstream raw materials:

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

acetyl chloride

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