(E)-3-[(4R,5R)-2,2-dimethyl-5-phenyl-1,3-dioxolan-4-yl]prop-2-en-1-ol

Base Information

• Chemical Name: (E)-3-[(4R,5R)-2,2-dimethyl-5-phenyl-1,3-dioxolan-4-yl]prop-2-en-1-ol
• CAS No.: 371978-06-2
• Molecular Formula: C₁₄H₁₈O₃
• Molecular Weight: 234.295
• Mol file: 371978-06-2.mol

Synonyms:(E)-3-[(4R,5R)-2,2-dimethyl-5-phenyl-1,3-dioxolan-4-yl]prop-2-en-1-ol

Chemical Property of (E)-3-[(4R,5R)-2,2-dimethyl-5-phenyl-1,3-dioxolan-4-yl]prop-2-en-1-ol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (E)-3-[(4R,5R)-2,2-dimethyl-5-phenyl-1,3-dioxolan-4-yl]prop-2-en-1-ol

There total 7 articles about (E)-3-[(4R,5R)-2,2-dimethyl-5-phenyl-1,3-dioxolan-4-yl]prop-2-en-1-ol 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: 91.0%

acetone (67-64-1) + (1R,2R,3E)-1-phenyl-pent-3-en-1,2,5-triol (371978-05-1) → (E)-3-[(4R,5R)-2,2-dimethyl-5-phenyl-1,3-dioxolan-4-yl]prop-2-en-1-ol (371978-06-2)

Guidance literature:

With toluene-4-sulfonic acid; copper(II) sulfate; at 20 ℃; for 48h;

DOI:10.1016/S0040-4020(01)00689-5

Reference yield: 84.0%

ethyl (E)-3-[(4R,5R)-2,2-dimethyl-5-phenyl-1,3-dioxolan-4-yl]prop-2-enoate (326603-41-2) → (E)-3-[(4R,5R)-2,2-dimethyl-5-phenyl-1,3-dioxolan-4-yl]prop-2-en-1-ol (371978-06-2)

Guidance literature:

With diisobutylaluminium hydride; In hexane; dichloromethane; at 0 ℃; for 2h;

DOI:10.1055/s-2007-965879

Reference yield:

ethyl (2E,4E)-5-phenyl-penta-2,4-dienoate (39806-16-1) → (E)-3-[(4R,5R)-2,2-dimethyl-5-phenyl-1,3-dioxolan-4-yl]prop-2-en-1-ol (371978-06-2)

Guidance literature:

Multi-step reaction with 3 steps

1: 78 percent / AD-mix-β; H2O / MsNH2 / 2-methyl-propan-2-ol / 18 h / 0 °C

2: 95 percent / PPTS / acetone / 12 h / 20 °C

3: 84 percent / DIBAL-H / CH₂Cl₂; hexane / 2 h / 0 °C

With AD-mix-β; water; pyridinium p-toluenesulfonate; diisobutylaluminium hydride; methanesulfonamide; In hexane; dichloromethane; acetone; tert-butyl alcohol;

DOI:10.1055/s-2007-965879

upstream raw materials:

acetone

(1R,2R,3E)-1-phenyl-pent-3-en-1,2,5-triol

ethyl (E)-3-[(4R,5R)-2,2-dimethyl-5-phenyl-1,3-dioxolan-4-yl]prop-2-enoate

ethyl (2E,4E)-5-phenyl-penta-2,4-dienoate

Downstream raw materials:

(3S,4R)-3-(tert-Butyl-dimethyl-silanyloxy)-4-((4R,5R)-2,2-dimethyl-5-phenyl-[1,3]dioxolan-4-yl)-pentanenitrile

(3S,4S,5R,6R)-3-tert-butyldimethylsilyloxy-5,6-di-O-isopropylidenedioxy-4-methyl-6-phenyl-hexanal

(3S,4S)-4-((4R,5R)-2,2-Dimethyl-5-phenyl-[1,3]dioxolan-4-yl)-3-hydroxy-pentanenitrile

(1R,2R,3S,4R)-1,2-di-O-isopropylidene-3-methyl-1-phenyl-pentan-1,2,4,5-tetrol