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

Base Information

• Chemical Name: (1R)-1-[(4S,5R)-2,2-dimethyl-5-phenyl-1,3-dioxolan-4-yl]but-3-enyl acrylate
• CAS No.: 473543-41-8
• Molecular Formula: C₁₈H₂₂O₄
• Molecular Weight: 302.37
• Mol file: 473543-41-8.mol

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

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

There total 8 articles about (1R)-1-[(4S,5R)-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: 47.0%

acrylic acid anhydride (2051-76-5) + (1R)-1-((4S,5R)-2,2-dimethyl-5-phenyl-[1,3]-dioxolan-4-yl)-3-buten-1-ol (473543-39-4) → (1R)-1-[(4S,5R)-2,2-dimethyl-5-phenyl-1,3-dioxolan-4-yl]but-3-enyl acrylate (473543-41-8)

Guidance literature:

With dmap; In tetrahydrofuran; at -20 - 18 ℃;

DOI:10.1071/CH02242

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:

(4S-cis)-5-[2'-(hydroxymethyl)phenyl]-2,2-dimethyl-1,3-dioxolane-4-methanol (160707-67-5) → (1R)-1-[(4S,5R)-2,2-dimethyl-5-phenyl-1,3-dioxolan-4-yl]but-3-enyl acrylate (473543-41-8)

Guidance literature:

Multi-step reaction with 7 steps

1: 70 percent / 'precipitated active' manganese dioxide / 1,2-dimethoxy-ethane / 16 h / 18 °C

2: 55 percent / pyridine; DMAP / CH₂Cl₂ / 17 h / 18 °C

3: 92 percent / [Rh(dppp)2]⁺*BF₄^- / xylene / 22 h / Heating

4: 96 percent / potassium carbonate / methanol / 0.5 h

5: 62 percent / NMO; tetrapropylammonium perruthenate(VII); molecular sieves 4 Angstroem / CH₂Cl₂ / 1 h / 0 °C

6: lithium perchlorate / diethyl ether / 4 h / 18 °C

7: 47 percent / DMAP / tetrahydrofuran / -20 - 18 °C

With pyridine; dmap; manganese(IV) oxide; N-methyl-2-indolinone; tetrapropylammonium perruthennate; 4 A molecular sieve; lithium perchlorate; potassium carbonate; [Rh(1,3-bis(diphenylphosphino)propane)2]BF₄; In tetrahydrofuran; methanol; 1,2-dimethoxyethane; diethyl ether; dichloromethane; xylene;

DOI:10.1071/CH02242

upstream raw materials:

acrylic acid anhydride

(1R)-1-((4S,5R)-2,2-dimethyl-5-phenyl-[1,3]-dioxolan-4-yl)-3-buten-1-ol

B-allyldiisopinocampheylborane

2,2-dimethoxy-propane

Downstream raw materials:

(+)-goniodiol

(6R,4'S,5'R)-6-(2',2'-dimethyl-5'-phenyl-[1',3']dioxolan-4'-yl)-5,6-dihydropyran-2-one