(R)-1-(3-[1,3]Dioxolan-2-ylmethyl-phenyl)-4-triisopropylsilanyloxy-butan-2-ol

Base Information

• Chemical Name: (R)-1-(3-[1,3]Dioxolan-2-ylmethyl-phenyl)-4-triisopropylsilanyloxy-butan-2-ol
• CAS No.: 479196-32-2
• Molecular Formula: C₂₃H₄₀O₄Si
• Molecular Weight: 408.654
• Mol file: 479196-32-2.mol

Synonyms:(R)-1-(3-[1,3]Dioxolan-2-ylmethyl-phenyl)-4-triisopropylsilanyloxy-butan-2-ol

Chemical Property of (R)-1-(3-[1,3]Dioxolan-2-ylmethyl-phenyl)-4-triisopropylsilanyloxy-butan-2-ol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (R)-1-(3-[1,3]Dioxolan-2-ylmethyl-phenyl)-4-triisopropylsilanyloxy-butan-2-ol

There total 8 articles about (R)-1-(3-[1,3]Dioxolan-2-ylmethyl-phenyl)-4-triisopropylsilanyloxy-butan-2-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:

(E)-4-[3-((E)-4-Hydroxy-but-2-enyl)-phenyl]-but-2-en-1-ol (479196-17-3) → (R)-1-(3-[1,3]Dioxolan-2-ylmethyl-phenyl)-4-triisopropylsilanyloxy-butan-2-ol (479196-32-2)

Guidance literature:

Multi-step reaction with 6 steps

1.1: NaH / tetrahydrofuran

1.2: 73 percent / tetrahydrofuran

2.1: 86 percent / t-BuO₂H; Ti(i-PrO)4; (-)-DIPT

3.1: 96 percent / Red-Al / tetrahydrofuran / -15 °C

4.1: 91 percent / imidazole / CH₂Cl₂

5.1: O₃ / CH₂Cl₂ / -78 °C

5.2: PPh₃ / CH₂Cl₂

6.1: TsOH / benzene / Heating

With 1H-imidazole; titanium(IV) isopropylate; tert.-butylhydroperoxide; sodium hydride; D-(-)-diisopropyl tartrate; toluene-4-sulfonic acid; ozone; sodium bis(2-methoxyethoxy)aluminium dihydride; In tetrahydrofuran; dichloromethane; benzene; 2.1: Sharpless asymmetric epoxidation;

DOI:10.1039/b207383h

Reference yield:

(E)-4-{3-[(E)-4-(tert-Butyl-dimethyl-silanyloxy)-but-2-enyl]-phenyl}-but-2-en-1-ol (479196-29-7) → (R)-1-(3-[1,3]Dioxolan-2-ylmethyl-phenyl)-4-triisopropylsilanyloxy-butan-2-ol (479196-32-2)

Guidance literature:

Multi-step reaction with 5 steps

1.1: 86 percent / t-BuO₂H; Ti(i-PrO)4; (-)-DIPT

2.1: 96 percent / Red-Al / tetrahydrofuran / -15 °C

3.1: 91 percent / imidazole / CH₂Cl₂

4.1: O₃ / CH₂Cl₂ / -78 °C

4.2: PPh₃ / CH₂Cl₂

5.1: TsOH / benzene / Heating

With 1H-imidazole; titanium(IV) isopropylate; tert.-butylhydroperoxide; D-(-)-diisopropyl tartrate; toluene-4-sulfonic acid; ozone; sodium bis(2-methoxyethoxy)aluminium dihydride; In tetrahydrofuran; dichloromethane; benzene; 1.1: Sharpless asymmetric epoxidation;

DOI:10.1039/b207383h

Reference yield:

C24H24N2S2 (479196-16-2) → (R)-1-(3-[1,3]Dioxolan-2-ylmethyl-phenyl)-4-triisopropylsilanyloxy-butan-2-ol (479196-32-2)

Guidance literature:

Multi-step reaction with 7 steps

1.1: m-CPBA / methanol

1.2: 81 percent / Et₂NH / methanol

2.1: NaH / tetrahydrofuran

2.2: 73 percent / tetrahydrofuran

3.1: 86 percent / t-BuO₂H; Ti(i-PrO)4; (-)-DIPT

4.1: 96 percent / Red-Al / tetrahydrofuran / -15 °C

5.1: 91 percent / imidazole / CH₂Cl₂

6.1: O₃ / CH₂Cl₂ / -78 °C

6.2: PPh₃ / CH₂Cl₂

7.1: TsOH / benzene / Heating

With 1H-imidazole; titanium(IV) isopropylate; tert.-butylhydroperoxide; sodium hydride; D-(-)-diisopropyl tartrate; toluene-4-sulfonic acid; ozone; 3-chloro-benzenecarboperoxoic acid; sodium bis(2-methoxyethoxy)aluminium dihydride; In tetrahydrofuran; methanol; dichloromethane; benzene; 1.2: Mislow-Evans rearrangement / 3.1: Sharpless asymmetric epoxidation;

DOI:10.1039/b207383h

upstream raw materials:

ethylene glycol

(E)-4-[3-((E)-4-Hydroxy-but-2-enyl)-phenyl]-but-2-en-1-ol

(E)-4-{3-[(E)-4-(tert-Butyl-dimethyl-silanyloxy)-but-2-enyl]-phenyl}-but-2-en-1-ol

C₂₄H₂₄N₂S₂

Downstream raw materials:

(R)-1-(5-[1,3]Dioxolan-2-ylmethyl-cyclohexa-1,4-dienyl)-4-triisopropylsilanyloxy-butan-2-ol