2-Propenoic acid, (1R,2R)-1-[(1S)-2-[[(1,1-dimethylethyl)diphenylsilyl]oxy]-1-methylethyl]-2 -methyl-3-buten-1-yl ester

Base Information

• Chemical Name: 2-Propenoic acid, (1R,2R)-1-[(1S)-2-[[(1,1-dimethylethyl)diphenylsilyl]oxy]-1-methylethyl]-2 -methyl-3-buten-1-yl ester
• CAS No.: 924286-81-7
• Molecular Formula: C27H36O3Si
• Molecular Weight: 436.667
• Mol file: 924286-81-7.mol

Synonyms:

Chemical Property of 2-Propenoic acid, (1R,2R)-1-[(1S)-2-[[(1,1-dimethylethyl)diphenylsilyl]oxy]-1-methylethyl]-2 -methyl-3-buten-1-yl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 2-Propenoic acid, (1R,2R)-1-[(1S)-2-[[(1,1-dimethylethyl)diphenylsilyl]oxy]-1-methylethyl]-2 -methyl-3-buten-1-yl ester

There total 5 articles about 2-Propenoic acid, (1R,2R)-1-[(1S)-2-[[(1,1-dimethylethyl)diphenylsilyl]oxy]-1-methylethyl]-2 -methyl-3-buten-1-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: 75.0%

(3R,4R,5S)-6-(tert-butyldiphenylsiloxy)-4-hydroxy-3,5-dimethylhexan-1-ene (91751-27-8,91797-99-8,91798-00-4,91798-01-5,106357-24-8,106357-26-0,106357-27-1,106357-25-9) + acryloyl chloride (814-68-6,25189-84-8) → (2S,3R,4R)-3-acryloxy-1-(tert-butyldiphenylsilyloxy)-2,4-dimethylhex-5-ene (924286-81-7)

Guidance literature:

With N-ethyl-N,N-diisopropylamine; In dichloromethane; at 25 ℃; for 2h;

DOI:10.1021/ja066477d

Reference yield:

(2S)-3-{[tert-butyl(diphenyl)silyl]oxy}-2-methylpropanal (92817-88-4) → (2S,3R,4R)-3-acryloxy-1-(tert-butyldiphenylsilyloxy)-2,4-dimethylhex-5-ene (924286-81-7)

Guidance literature:

Multi-step reaction with 2 steps

1: 75 percent / iPr₂NEt / CH₂Cl₂ / 2 h / 25 °C

With N-ethyl-N,N-diisopropylamine; In dichloromethane;

DOI:10.1021/ja066477d

Reference yield:

(S)-3-(tert-butyl-diphenyl-silanyloxy)-2-methyl-propionic acid methyl ester (95514-03-7) → (2S,3R,4R)-3-acryloxy-1-(tert-butyldiphenylsilyloxy)-2,4-dimethylhex-5-ene (924286-81-7)

Guidance literature:

Multi-step reaction with 4 steps

1: 87 percent / DIBAL-H / toluene / 1 h / -78 °C

2: 95 percent / NMO; TPAP; molecular sieves 4 Angstroem / CH₂Cl₂ / 0.5 h / 0 °C

3: 75 percent / iPr₂NEt / CH₂Cl₂ / 2 h / 25 °C

With N-methyl-2-indolinone; tetrapropylammonium perruthennate; 4 A molecular sieve; diisobutylaluminium hydride; N-ethyl-N,N-diisopropylamine; In dichloromethane; toluene;

DOI:10.1021/ja066477d

upstream raw materials:

(3R,4R,5S)-6-(tert-butyldiphenylsiloxy)-4-hydroxy-3,5-dimethylhexan-1-ene

acryloyl chloride

(2S)-3-{[tert-butyl(diphenyl)silyl]oxy}-2-methylpropanal

(R)-3-(tert-butyldiphenylsilyloxy)-2-methylpropan-1-ol