(E)-1-{(3R,3aS,6R)-6-Benzyloxy-3-[dimethyl-(1,1,2-trimethyl-propyl)-silanyloxy]-2,2-dimethyl-2,3,3a,4,5,6-hexahydro-pentalen-1-yl}-3-trimethylsilanyl-prop-2-en-1-ol

Base Information

• Chemical Name: (E)-1-{(3R,3aS,6R)-6-Benzyloxy-3-[dimethyl-(1,1,2-trimethyl-propyl)-silanyloxy]-2,2-dimethyl-2,3,3a,4,5,6-hexahydro-pentalen-1-yl}-3-trimethylsilanyl-prop-2-en-1-ol
• CAS No.: 125184-69-2
• Molecular Formula: C₃₁H₅₂O₃Si₂
• Molecular Weight: 528.923
• Mol file: 125184-69-2.mol

Synonyms:(E)-1-{(3R,3aS,6R)-6-Benzyloxy-3-[dimethyl-(1,1,2-trimethyl-propyl)-silanyloxy]-2,2-dimethyl-2,3,3a,4,5,6-hexahydro-pentalen-1-yl}-3-trimethylsilanyl-prop-2-en-1-ol

Chemical Property of (E)-1-{(3R,3aS,6R)-6-Benzyloxy-3-[dimethyl-(1,1,2-trimethyl-propyl)-silanyloxy]-2,2-dimethyl-2,3,3a,4,5,6-hexahydro-pentalen-1-yl}-3-trimethylsilanyl-prop-2-en-1-ol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (E)-1-{(3R,3aS,6R)-6-Benzyloxy-3-[dimethyl-(1,1,2-trimethyl-propyl)-silanyloxy]-2,2-dimethyl-2,3,3a,4,5,6-hexahydro-pentalen-1-yl}-3-trimethylsilanyl-prop-2-en-1-ol

There total 16 articles about (E)-1-{(3R,3aS,6R)-6-Benzyloxy-3-[dimethyl-(1,1,2-trimethyl-propyl)-silanyloxy]-2,2-dimethyl-2,3,3a,4,5,6-hexahydro-pentalen-1-yl}-3-trimethylsilanyl-prop-2-en-1-ol 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: 92.0%

<β-(Trimethylsilyl)vinyl>magnesium bromide (42201-74-1,78012-49-4) + (3R,3aS)-6-Benzyloxy-3-[dimethyl-(1,1,2-trimethyl-propyl)-silanyloxy]-2,2-dimethyl-2,3,3a,4,5,6-hexahydro-pentalene-1-carbaldehyde (125184-68-1,134747-97-0) → (E)-1-{(3R,3aS)-6-Benzyloxy-3-[dimethyl-(1,1,2-trimethyl-propyl)-silanyloxy]-2,2-dimethyl-2,3,3a,4,5,6-hexahydro-pentalen-1-yl}-3-trimethylsilanyl-prop-2-en-1-ol (125184-69-2)

Guidance literature:

In tetrahydrofuran; at -30 - 0 ℃;

DOI:10.1016/S0040-4039(00)99432-2

Reference yield: 85.0%

2-trimethylsilylethenylmagnesium bromide (42201-74-1,78012-49-4) + (3R,3aS,6R)-6-Benzyloxy-3-[dimethyl-(1,1,2-trimethyl-propyl)-silanyloxy]-2,2-dimethyl-2,3,3a,4,5,6-hexahydro-pentalene-1-carbaldehyde (125184-68-1,134747-97-0) → (E)-1-{(3R,3aS,6R)-6-Benzyloxy-3-[dimethyl-(1,1,2-trimethyl-propyl)-silanyloxy]-2,2-dimethyl-2,3,3a,4,5,6-hexahydro-pentalen-1-yl}-3-trimethylsilanyl-prop-2-en-1-ol (125184-69-2)

Guidance literature:

In tetrahydrofuran; at -30 ℃;

DOI:10.1016/S0040-4039(00)71256-1

Reference yield:

1-carbomethoxy-3,3-dimethylcyclopropene (21603-22-5) → (E)-1-{(3R,3aS)-6-Benzyloxy-3-[dimethyl-(1,1,2-trimethyl-propyl)-silanyloxy]-2,2-dimethyl-2,3,3a,4,5,6-hexahydro-pentalen-1-yl}-3-trimethylsilanyl-prop-2-en-1-ol (125184-69-2)

Guidance literature:

Multi-step reaction with 6 steps

1: diethyl ether / 36 h / 25 °C

2: 96 percent / H₂SO₄ / benzene / 12 h / Heating

3: NEt₃ / CH₂Cl₂ / 0.5 h / Heating

4: DIBAL / benzene / 0.5 h / 25 °C

5: PDC / CH₂Cl₂ / 7 h / 25 °C

6: 92 percent / tetrahydrofuran / -30 - 0 °C

With dipyridinium dichromate; sulfuric acid; diisobutylaluminium hydride; triethylamine; In tetrahydrofuran; diethyl ether; dichloromethane; benzene;

DOI:10.1016/S0040-4039(00)99432-2

upstream raw materials:

2-trimethylsilylethenylmagnesium bromide

(3R,3aS,6R)-6-Benzyloxy-3-[dimethyl-(1,1,2-trimethyl-propyl)-silanyloxy]-2,2-dimethyl-2,3,3a,4,5,6-hexahydro-pentalene-1-carbaldehyde

O-benzyl 2,2,2-trichloroacetimidate

(3R,3aS)-3-Hydroxy-2,2-dimethyl-2,3,3a,4,5,6-hexahydro-pentalene-1-carboxylic acid ethyl ester

Downstream raw materials:

(E)-1-{(3R,3aS,6R)-6-Benzyloxy-3-[dimethyl-(1,1,2-trimethyl-propyl)-silanyloxy]-2,2-dimethyl-2,3,3a,4,5,6-hexahydro-pentalen-1-yl}-3-trimethylsilanyl-propenone

(E)-1-{(3R,3aS)-6-Benzyloxy-3-[dimethyl-(1,1,2-trimethyl-propyl)-silanyloxy]-2,2-dimethyl-2,3,3a,4,5,6-hexahydro-pentalen-1-yl}-3-trimethylsilanyl-propenone