3-((4R,5R)-5-Benzyl-2,2-dimethyl-[1,3]dioxolan-4-yl)-propionic acid

Base Information

• Chemical Name: 3-((4R,5R)-5-Benzyl-2,2-dimethyl-[1,3]dioxolan-4-yl)-propionic acid
• CAS No.: 151692-01-2
• Molecular Formula: C₁₅H₂₀O₄
• Molecular Weight: 264.321
• Mol file: 151692-01-2.mol

Synonyms:3-((4R,5R)-5-Benzyl-2,2-dimethyl-[1,3]dioxolan-4-yl)-propionic acid

Chemical Property of 3-((4R,5R)-5-Benzyl-2,2-dimethyl-[1,3]dioxolan-4-yl)-propionic acid

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 3-((4R,5R)-5-Benzyl-2,2-dimethyl-[1,3]dioxolan-4-yl)-propionic acid

There total 17 articles about 3-((4R,5R)-5-Benzyl-2,2-dimethyl-[1,3]dioxolan-4-yl)-propionic acid 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:

3-((4R,5R)-5-Benzyl-2,2-dimethyl-[1,3]dioxolan-4-yl)-propionaldehyde (140844-93-5) → 3-((4R,5R)-5-Benzyl-2,2-dimethyl-[1,3]dioxolan-4-yl)-propionic acid (151692-01-2)

Guidance literature:

With potassium hydroxide; silver nitrate; In methanol; water; at 0 ℃; for 0.5h;

DOI:10.1246/bcsj.64.721

Reference yield:

phenylethynylmagnesium bromide (6738-06-3) → 3-((4R,5R)-5-Benzyl-2,2-dimethyl-[1,3]dioxolan-4-yl)-propionic acid (151692-01-2)

Guidance literature:

Multi-step reaction with 11 steps

1: 1.) ethyl chloroformate, triethylamine / 1.) toluene, -20 deg C, 2 h, 2.) THF, -40 deg C, 1 h

2: 86 percent / sodium borohydride / methanol / 1 h / Ambient temperature

3: diethyl ether / 48 h / 20 °C / pig pancreatic lipase

4: lithium aluminum hydride / tetrahydrofuran / 20 h / Heating

5: imidazole / dimethylformamide / 1 h / 0 °C

6: 93 percent / monoperphthalic acid monomagnesium salt, 2 N sodium hydroxide / propan-2-ol; H₂O / 2 h / Ambient temperature

7: hydrogen / 10 percent palladium on carbon / ethanol / 1 h / Ambient temperature

8: p-toluenesulfonic acid / 2 h / Ambient temperature

9: tetrabutylammonium fluoride / tetrahydrofuran / 1 h / Ambient temperature

10: 1.) oxalyl chloride, dimethyl sulfoxide, 2.) triethylamine / 1.) dichloromethane, -70 deg C, 1 h, 2.) dichloromethane, -> -10 deg C

11: AgNO₃, KOH, H₂O / methanol

With 1H-imidazole; potassium hydroxide; sodium hydroxide; sodium tetrahydroborate; lithium aluminium tetrahydride; oxalyl dichloride; tetrabutyl ammonium fluoride; water; hydrogen; chloroformic acid ethyl ester; toluene-4-sulfonic acid; magnesium monoperoxyphthalate hexahydrate; silver nitrate; dimethyl sulfoxide; triethylamine; palladium on activated charcoal; In tetrahydrofuran; methanol; diethyl ether; ethanol; water; N,N-dimethyl-formamide; isopropyl alcohol;

Reference yield:

4-oxo-6-phenyl-5-hexynoic acid methyl ester (59700-84-4) → 3-((4R,5R)-5-Benzyl-2,2-dimethyl-[1,3]dioxolan-4-yl)-propionic acid (151692-01-2)

Guidance literature:

Multi-step reaction with 10 steps

1: 86 percent / sodium borohydride / methanol / 1 h / Ambient temperature

2: diethyl ether / 48 h / 20 °C / pig pancreatic lipase

3: lithium aluminum hydride / tetrahydrofuran / 20 h / Heating

4: imidazole / dimethylformamide / 1 h / 0 °C

5: 93 percent / monoperphthalic acid monomagnesium salt, 2 N sodium hydroxide / propan-2-ol; H₂O / 2 h / Ambient temperature

6: hydrogen / 10 percent palladium on carbon / ethanol / 1 h / Ambient temperature

7: p-toluenesulfonic acid / 2 h / Ambient temperature

8: tetrabutylammonium fluoride / tetrahydrofuran / 1 h / Ambient temperature

9: 1.) oxalyl chloride, dimethyl sulfoxide, 2.) triethylamine / 1.) dichloromethane, -70 deg C, 1 h, 2.) dichloromethane, -> -10 deg C

10: AgNO₃, KOH, H₂O / methanol

With 1H-imidazole; potassium hydroxide; sodium hydroxide; sodium tetrahydroborate; lithium aluminium tetrahydride; oxalyl dichloride; tetrabutyl ammonium fluoride; water; hydrogen; toluene-4-sulfonic acid; magnesium monoperoxyphthalate hexahydrate; silver nitrate; dimethyl sulfoxide; triethylamine; palladium on activated charcoal; In tetrahydrofuran; methanol; diethyl ether; ethanol; water; N,N-dimethyl-formamide; isopropyl alcohol;

upstream raw materials:

3-((4R,5R)-5-Benzyl-2,2-dimethyl-[1,3]dioxolan-4-yl)-propionaldehyde

phenylethynylmagnesium bromide

4-oxo-6-phenyl-5-hexynoic acid methyl ester

(3R)-6-t-butyldimethylsilyloxy-1,2-epoxy-1-phenylhexane-3-ol

Downstream raw materials:

(4R,5R)-5-hydroxy-6-phenyl-4-hexanolide

(R)-5-((S)-1-Hydroxy-2-phenyl-ethyl)-dihydro-furan-2-one

Acetic acid (S)-1-((R)-5-oxo-tetrahydro-furan-2-yl)-2-phenyl-ethyl ester

Methanesulfonic acid (R)-1-((R)-5-oxo-tetrahydro-furan-2-yl)-2-phenyl-ethyl ester