(1S)-1-[(4R,5S)-2,2-dimethyl-5-phenyl-1,3-dioxolan-4-yl]but-3-enyl acrylate

Base Information

• Chemical Name: (1S)-1-[(4R,5S)-2,2-dimethyl-5-phenyl-1,3-dioxolan-4-yl]but-3-enyl acrylate
• CAS No.: 936210-32-1
• Molecular Formula: C₁₈H₂₂O₄
• Molecular Weight: 302.37
• Mol file: 936210-32-1.mol

Synonyms:(1S)-1-[(4R,5S)-2,2-dimethyl-5-phenyl-1,3-dioxolan-4-yl]but-3-enyl acrylate

Chemical Property of (1S)-1-[(4R,5S)-2,2-dimethyl-5-phenyl-1,3-dioxolan-4-yl]but-3-enyl acrylate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (1S)-1-[(4R,5S)-2,2-dimethyl-5-phenyl-1,3-dioxolan-4-yl]but-3-enyl acrylate

There total 4 articles about (1S)-1-[(4R,5S)-2,2-dimethyl-5-phenyl-1,3-dioxolan-4-yl]but-3-enyl acrylate 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:

(2E)-3-phenyl-2-propen-1-ol (4407-36-7) → (1S)-1-[(4R,5S)-2,2-dimethyl-5-phenyl-1,3-dioxolan-4-yl]but-3-enyl acrylate (936210-32-1)

Guidance literature:

Multi-step reaction with 3 steps

1: LiBEt₃H / tetrahydrofuran / 1 h / -78 °C

2: ethyldiisopropylamine; 4-(dimethylamino)pyridine / CH₂Cl₂ / 5 h / 0 °C

With dmap; lithium triethylborohydride; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; dichloromethane;

DOI:10.1246/bcsj.80.387

Reference yield:

B-allyldiisopinocampheylborane (106356-53-0) + 2,2-dimethoxy-propane (77-76-9) + acryloyl chloride (814-68-6,25189-84-8) + (2E)-3-phenyl-2-propen-1-ol (4407-36-7) → (1S)-1-[(4R,5S)-2,2-dimethyl-5-phenyl-1,3-dioxolan-4-yl]but-3-enyl acrylate (936210-32-1) + (1R)-1-[(4R,5S)-2,2-dimethyl-5-phenyl-1,3-dioxolan-4-yl]but-3-enyl acrylate (936210-33-2) + (1S)-1-[(4S,5R)-2,2-dimethyl-5-phenyl-1,3-dioxolan-4-yl]but-3-enyl acrylate (473543-40-7) + (1R)-1-[(4S,5R)-2,2-dimethyl-5-phenyl-1,3-dioxolan-4-yl]but-3-enyl acrylate (473543-41-8)

Guidance literature:

Multistep reaction.;

DOI:10.1246/bcsj.80.387

Reference yield:

C15H20O3 + acryloyl chloride (814-68-6,25189-84-8) → (1S)-1-[(4R,5S)-2,2-dimethyl-5-phenyl-1,3-dioxolan-4-yl]but-3-enyl acrylate (936210-32-1) + (1R)-1-[(4R,5S)-2,2-dimethyl-5-phenyl-1,3-dioxolan-4-yl]but-3-enyl acrylate (936210-33-2)

Guidance literature:

With dmap; N-ethyl-N,N-diisopropylamine; In dichloromethane; at 0 ℃; for 5h;

DOI:10.1246/bcsj.80.387

upstream raw materials:

acryloyl chloride

B-allyldiisopinocampheylborane

2,2-dimethoxy-propane

(2E)-3-phenyl-2-propen-1-ol

Downstream raw materials:

(6S)-6-[(4R,5S)-2,2-dimethyl-5-phenyl-1,3-dioxolan-4-yl]-5,6-dihydro-2H-pyran-2-one

(6S,7S,8S)-(-)-goniodiol