(4S,5R)-5-allyl-4-(tert-butyldimethylsiloxy)cyclohex-2-enone

Base Information

• Chemical Name: (4S,5R)-5-allyl-4-(tert-butyldimethylsiloxy)cyclohex-2-enone
• CAS No.: 157035-24-0
• Molecular Formula: C₁₅H₂₆O₂Si
• Molecular Weight: 266.456
• Mol file: 157035-24-0.mol

Synonyms:(4S,5R)-5-allyl-4-(tert-butyldimethylsiloxy)cyclohex-2-enone

Chemical Property of (4S,5R)-5-allyl-4-(tert-butyldimethylsiloxy)cyclohex-2-enone

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (4S,5R)-5-allyl-4-(tert-butyldimethylsiloxy)cyclohex-2-enone

There total 10 articles about (4S,5R)-5-allyl-4-(tert-butyldimethylsiloxy)cyclohex-2-enone 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: 85.0%

(1S,4R,4aS,7R,8S,8aR)-7-Allyl-8-(tert-butyl-dimethyl-silanyloxy)-4,4a,6,7,8,8a-hexahydro-1H-1,4-methano-naphthalen-5-one (864155-60-2) → (4S,5R)-5-allyl-4-(tert-butyldimethylsiloxy)cyclohex-2-enone (157035-24-0)

Guidance literature:

With diphenylether; at 210 ℃; for 0.25h;

DOI:10.1039/b505264e

Reference yield: 84.0%

tert-butyldimethylsilyl chloride (18162-48-6) + (3R,4S,5R)-5-allyl-3,4-(isopropylidenedioxy)cyclohexanone (157035-23-9) → (4S,5R)-5-allyl-4-(tert-butyldimethylsiloxy)cyclohex-2-enone (157035-24-0)

Guidance literature:

With 1,8-diazabicyclo[5.4.0]undec-7-ene; In benzene; Heating;

DOI:10.1016/S0040-4039(00)73333-8

Reference yield:

(1S,4R,4aS,5R,8S,8aR)-5-Allyl-8-(tert-butyl-dimethyl-silanyloxy)-1,4,4a,5,8,8a-hexahydro-1,4-methano-naphthalen-5-ol (864155-59-9) → (4S,5R)-5-allyl-4-(tert-butyldimethylsiloxy)cyclohex-2-enone (157035-24-0)

Guidance literature:

Multi-step reaction with 2 steps

1: 81 percent / KH / dioxane / 0.5 h / 85 °C

2: 85 percent / diphenyl ether / 0.25 h / 210 °C

With diphenylether; potassium hydride; In 1,4-dioxane; 1: oxy-Cope rearrangement / 2: retro-Diels-Alder;

DOI:10.1039/b505264e

upstream raw materials:

tert-butyldimethylsilyl chloride

(3R,4S,5R)-5-allyl-3,4-(isopropylidenedioxy)cyclohexanone

(1S,4R,4aS,7R,8S,8aR)-7-Allyl-8-(tert-butyl-dimethyl-silanyloxy)-4,4a,6,7,8,8a-hexahydro-1H-1,4-methano-naphthalen-5-one

(1S,4R,4aS,5R,8S,8aR)-5-Allyl-8-(tert-butyl-dimethyl-silanyloxy)-1,4,4a,5,8,8a-hexahydro-1,4-methano-naphthalen-5-ol

Downstream raw materials:

2-[(1R,2R,3R)-2-Allyl-3-(tert-butyl-dimethyl-silanyloxy)-6-oxo-cyclohexyl]-N-benzyl-N-(4-methoxy-benzyl)-acetamide

(3R,4R)-4-tert-butyldimethylsiloxy-3-(2-propenyl)cyclohexanone

[(1R,5R,6R)-6-Allyl-5-(tert-butyl-dimethyl-silanyloxy)-2-oxo-cyclohex-3-enyl]-acetic acid ethyl ester

(4S,8aR,12S,12aR)-12-[[(1,1-dimethylethyl)diphenylsilyl]oxy]-4,5,6,7,8,8a,12,12a-octahydro-4-methyl-2H-3-benzoxecin-2,9(1H)-dione