(-)-(2R,4S)-2-[(3R,E)-5-(tert-butyldiphenylsiloxy)penten-3-yl]-2,4-dimethyl-3-methylene-4-carbomethoxycyclohexanone

Base Information

• Chemical Name: (-)-(2R,4S)-2-[(3R,E)-5-(tert-butyldiphenylsiloxy)penten-3-yl]-2,4-dimethyl-3-methylene-4-carbomethoxycyclohexanone
• CAS No.: 397322-74-6
• Molecular Formula: C₃₂H₄₂O₄Si
• Molecular Weight: 518.769
• Mol file: 397322-74-6.mol

Synonyms:(-)-(2R,4S)-2-[(3R,E)-5-(tert-butyldiphenylsiloxy)penten-3-yl]-2,4-dimethyl-3-methylene-4-carbomethoxycyclohexanone

Chemical Property of (-)-(2R,4S)-2-[(3R,E)-5-(tert-butyldiphenylsiloxy)penten-3-yl]-2,4-dimethyl-3-methylene-4-carbomethoxycyclohexanone

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (-)-(2R,4S)-2-[(3R,E)-5-(tert-butyldiphenylsiloxy)penten-3-yl]-2,4-dimethyl-3-methylene-4-carbomethoxycyclohexanone

There total 15 articles about (-)-(2R,4S)-2-[(3R,E)-5-(tert-butyldiphenylsiloxy)penten-3-yl]-2,4-dimethyl-3-methylene-4-carbomethoxycyclohexanone 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: 75.0%

(S)-4-[(E)-5-(tert-Butyl-diphenyl-silanyloxy)-pent-2-enyloxy]-1,3-dimethyl-2-methylene-cyclohex-3-enecarboxylic acid methyl ester (397322-69-9) → (-)-(2R,4S)-2-[(3R,E)-5-(tert-butyldiphenylsiloxy)penten-3-yl]-2,4-dimethyl-3-methylene-4-carbomethoxycyclohexanone (397322-74-6)

Guidance literature:

With trimethylaluminum; titanium tetrachloride; In dichloromethane; toluene; at -65 ℃; for 0.416667h; diastereoselective reaction; Inert atmosphere; Molecular sieve;

DOI:10.1016/j.tet.2011.09.067

Reference yield: 65.0%

(S)-4-[(E)-5-(tert-Butyl-diphenyl-silanyloxy)-pent-2-enyloxy]-1,3-dimethyl-2-methylene-cyclohex-3-enecarboxylic acid methyl ester (397322-69-9) → (1S,3S)-3-{(S)-1-[2-(tert-Butyl-diphenyl-silanyloxy)-ethyl]-allyl}-1,3-dimethyl-2-methylene-4-oxo-cyclohexanecarboxylic acid methyl ester + (-)-(2R,4S)-2-[(3R,E)-5-(tert-butyldiphenylsiloxy)penten-3-yl]-2,4-dimethyl-3-methylene-4-carbomethoxycyclohexanone (397322-74-6)

Guidance literature:

With 4 A molecular sieve; trimethylaluminum; titanium tetrachloride; In dichloromethane; toluene; at -65 ℃; for 0.416667h;

DOI:10.1021/ja017194i

Reference yield:

4-(tert-butyldiphenylsilyloxy)-1-butyne (88158-68-3) → (-)-(2R,4S)-2-[(3R,E)-5-(tert-butyldiphenylsiloxy)penten-3-yl]-2,4-dimethyl-3-methylene-4-carbomethoxycyclohexanone (397322-74-6)

Guidance literature:

Multi-step reaction with 5 steps

1.1: n-butyllithium / tetrahydrofuran; hexane / 3.5 h / -78 - 20 °C

1.2: 85 percent / tetrahydrofuran; hexane / 16 h / -78 - 20 °C

2.1: 96 percent / LAH / methanol; tetrahydrofuran / 1 h / Heating

3.1: 1,10-phenantroline; n-BuLi / diethyl ether / 0.25 h / -78 °C

4.1: KHMDS; HMPA / tetrahydrofuran / -78 - 20 °C

4.2: 65 percent / tetrahydrofuran / 0.5 h / -78 °C

5.1: 65 percent / TiCl₄; Me₃Al; 4 angstroem molecular sieves / CH₂Cl₂; toluene / 0.42 h / -65 °C

With N,N,N,N,N,N-hexamethylphosphoric triamide; lithium aluminium tetrahydride; n-butyllithium; 1,10-Phenanthroline; 4 A molecular sieve; trimethylaluminum; titanium tetrachloride; potassium hexamethylsilazane; In tetrahydrofuran; methanol; diethyl ether; hexane; dichloromethane; toluene; 5.1: Claisen rearrangement;

DOI:10.1021/ja017194i

upstream raw materials:

(S)-4-[(E)-5-(tert-Butyl-diphenyl-silanyloxy)-pent-2-enyloxy]-1,3-dimethyl-2-methylene-cyclohex-3-enecarboxylic acid methyl ester

2-acetylpropanoic acid ethyl ester

4-(tert-butyldiphenylsilyloxy)-1-butyne

(E)-5-(2,2-dimethyl-1,1-diphenyl-1-silapropoxy)pent-2-en-1-ol