4-[(4R,5S)-5-(3-Benzyloxy-propyl)-2,2,5-trimethyl-[1,3]dioxolan-4-yl]-butan-2-one

Base Information

• Chemical Name: 4-[(4R,5S)-5-(3-Benzyloxy-propyl)-2,2,5-trimethyl-[1,3]dioxolan-4-yl]-butan-2-one
• CAS No.: 148455-94-1
• Molecular Formula: C₂₀H₃₀O₄
• Molecular Weight: 334.456
• Mol file: 148455-94-1.mol

Synonyms:4-[(4R,5S)-5-(3-Benzyloxy-propyl)-2,2,5-trimethyl-[1,3]dioxolan-4-yl]-butan-2-one

Chemical Property of 4-[(4R,5S)-5-(3-Benzyloxy-propyl)-2,2,5-trimethyl-[1,3]dioxolan-4-yl]-butan-2-one

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 4-[(4R,5S)-5-(3-Benzyloxy-propyl)-2,2,5-trimethyl-[1,3]dioxolan-4-yl]-butan-2-one

There total 13 articles about 4-[(4R,5S)-5-(3-Benzyloxy-propyl)-2,2,5-trimethyl-[1,3]dioxolan-4-yl]-butan-2-one 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-(2-methyl-[1,3]dioxolan-2-yl)-propan-1-ol (29021-98-5) → 4-[(4R,5S)-5-(3-Benzyloxy-propyl)-2,2,5-trimethyl-[1,3]dioxolan-4-yl]-butan-2-one (148455-94-1)

Guidance literature:

Multi-step reaction with 12 steps

1: NaH / tetrahydrofuran / 3 h

2: PTSA / methanol / 3 h

3: 70 percent / NaH / benzene / 6 h / 60 °C

4: DIBAL-H / CH₂Cl₂ / 1 h / -15 °C

5: TBHP, Ti(OiPr)4, (+)-DIPT / CH₂Cl₂ / 6 h / -20 °C

6: 50 percent / 0.3N aq. KOH / dimethylsulfoxide / 12 h

7: imidazole / CH₂Cl₂ / 3 h

8: PTSA / CH₂Cl₂ / 0.17 h

9: Bu₄NF / tetrahydrofuran / 3 h

10: 1) (COCl)2, DMSO, 2) Et₃N / 1) CH₂Cl₂, -78 deg C, 1 h

11: CH₂Cl₂ / 3 h

12: H₂, NaHCO₃ / Pd-C / methanol / 3 h

With 1H-imidazole; titanium(IV) isopropylate; tert.-butylhydroperoxide; potassium hydroxide; oxalyl dichloride; L-(+)-diisopropyl tartrate; tetrabutyl ammonium fluoride; hydrogen; sodium hydride; diisobutylaluminium hydride; sodium hydrogencarbonate; toluene-4-sulfonic acid; dimethyl sulfoxide; triethylamine; palladium on activated charcoal; In tetrahydrofuran; methanol; dichloromethane; dimethyl sulfoxide; benzene;

DOI:10.1016/S0040-4039(00)60792-X

Reference yield:

(E)-4-[(4R,5S)-5-(3-Benzyloxy-propyl)-2,2,5-trimethyl-[1,3]dioxolan-4-yl]-but-3-en-2-one → 4-[(4R,5S)-5-(3-Benzyloxy-propyl)-2,2,5-trimethyl-[1,3]dioxolan-4-yl]-butan-2-one (148455-94-1)

Guidance literature:

With hydrogen; sodium hydrogencarbonate; palladium on activated charcoal; In methanol; for 3h;

DOI:10.1016/S0040-4039(00)60792-X

Reference yield:

benzyl bromide (100-39-0) → 4-[(4R,5S)-5-(3-Benzyloxy-propyl)-2,2,5-trimethyl-[1,3]dioxolan-4-yl]-butan-2-one (148455-94-1)

Guidance literature:

Multi-step reaction with 12 steps

1: NaH / tetrahydrofuran / 3 h

2: PTSA / methanol / 3 h

3: 70 percent / NaH / benzene / 6 h / 60 °C

4: DIBAL-H / CH₂Cl₂ / 1 h / -15 °C

5: TBHP, Ti(OiPr)4, (+)-DIPT / CH₂Cl₂ / 6 h / -20 °C

6: 50 percent / 0.3N aq. KOH / dimethylsulfoxide / 12 h

7: imidazole / CH₂Cl₂ / 3 h

8: PTSA / CH₂Cl₂ / 0.17 h

9: Bu₄NF / tetrahydrofuran / 3 h

10: 1) (COCl)2, DMSO, 2) Et₃N / 1) CH₂Cl₂, -78 deg C, 1 h

11: CH₂Cl₂ / 3 h

12: H₂, NaHCO₃ / Pd-C / methanol / 3 h

With 1H-imidazole; titanium(IV) isopropylate; tert.-butylhydroperoxide; potassium hydroxide; oxalyl dichloride; L-(+)-diisopropyl tartrate; tetrabutyl ammonium fluoride; hydrogen; sodium hydride; diisobutylaluminium hydride; sodium hydrogencarbonate; toluene-4-sulfonic acid; dimethyl sulfoxide; triethylamine; palladium on activated charcoal; In tetrahydrofuran; methanol; dichloromethane; dimethyl sulfoxide; benzene;

DOI:10.1016/S0040-4039(00)60792-X

upstream raw materials:

3-(2-methyl-[1,3]dioxolan-2-yl)-propan-1-ol

benzyl bromide

5-(benzyloxy)pentan-2-one

4-oxopentanoic acid ethyl ester

Downstream raw materials:

(E)-5-[(4R,5S)-5-(3-Benzyloxy-propyl)-2,2,5-trimethyl-[1,3]dioxolan-4-yl]-3-methyl-pent-2-enoic acid ethyl ester