(2R,3S,E)-tert-butyldimethyl[(3-methyl-5-phenylpent-4-en-2-yl)oxy]silane

Base Information

• Chemical Name: (2R,3S,E)-tert-butyldimethyl[(3-methyl-5-phenylpent-4-en-2-yl)oxy]silane
• CAS No.: 1351354-78-3
• Molecular Formula: C₁₈H₃₀OSi
• Molecular Weight: 290.521
• Mol file: 1351354-78-3.mol

Synonyms:(2R,3S,E)-tert-butyldimethyl[(3-methyl-5-phenylpent-4-en-2-yl)oxy]silane

Chemical Property of (2R,3S,E)-tert-butyldimethyl[(3-methyl-5-phenylpent-4-en-2-yl)oxy]silane

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2R,3S,E)-tert-butyldimethyl[(3-methyl-5-phenylpent-4-en-2-yl)oxy]silane

There total 5 articles about (2R,3S,E)-tert-butyldimethyl[(3-methyl-5-phenylpent-4-en-2-yl)oxy]silane 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: 37.0%

5-phenylsulfonyl-2-phenyl-2H-tetrazole + (2S,3R)-3-(tert-butyldimethylsilanyloxy)-2-methylbutyraldehyde (140223-32-1) → (2R,3S,Z)-tert-butyldimethyl[(3-methyl-5-phenylpent-4-en-2-yl)oxy]silane (1351354-77-2) + (2R,3S,E)-tert-butyldimethyl[(3-methyl-5-phenylpent-4-en-2-yl)oxy]silane (1351354-78-3)

Guidance literature:

5-phenylsulfonyl-2-phenyl-2H-tetrazole; With potassium hexamethylsilazane; In tetrahydrofuran; toluene; at -78 ℃; for 0.5h; Inert atmosphere;

(2S,3R)-3-(tert-butyldimethylsilanyloxy)-2-methylbutyraldehyde; In tetrahydrofuran; toluene; at -78 - 20 ℃; Inert atmosphere;

DOI:10.1021/ol202829u

Reference yield:

tert-butyldimethylsilyl chloride (18162-48-6) → (2R,3S,Z)-tert-butyldimethyl[(3-methyl-5-phenylpent-4-en-2-yl)oxy]silane (1351354-77-2) + (2R,3S,E)-tert-butyldimethyl[(3-methyl-5-phenylpent-4-en-2-yl)oxy]silane (1351354-78-3)

Guidance literature:

Multi-step reaction with 4 steps

1.1: 1H-imidazole / dichloromethane / 20 °C / Inert atmosphere

2.1: diisobutylaluminium hydride / dichloromethane; toluene / 1.5 h / -10 - 20 °C / Inert atmosphere

3.1: oxalyl dichloride; dimethyl sulfoxide / dichloromethane / 1 h / -78 °C / Inert atmosphere

3.2: 0.5 h / -78 °C / Inert atmosphere

4.1: potassium hexamethylsilazane / tetrahydrofuran; toluene / 0.5 h / -78 °C / Inert atmosphere

4.2: -78 - 20 °C / Inert atmosphere

With 1H-imidazole; oxalyl dichloride; potassium hexamethylsilazane; diisobutylaluminium hydride; dimethyl sulfoxide; In tetrahydrofuran; dichloromethane; toluene;

DOI:10.1021/ol202829u

Reference yield:

(2R,3R)-3-<(tert-Butyl)dimethylsilyloxy>-2-methylbuttersaeure-methylester (96597-33-0,155897-72-6) → (2R,3S,Z)-tert-butyldimethyl[(3-methyl-5-phenylpent-4-en-2-yl)oxy]silane (1351354-77-2) + (2R,3S,E)-tert-butyldimethyl[(3-methyl-5-phenylpent-4-en-2-yl)oxy]silane (1351354-78-3)

Guidance literature:

Multi-step reaction with 3 steps

1.1: diisobutylaluminium hydride / dichloromethane; toluene / 1.5 h / -10 - 20 °C / Inert atmosphere

2.1: oxalyl dichloride; dimethyl sulfoxide / dichloromethane / 1 h / -78 °C / Inert atmosphere

2.2: 0.5 h / -78 °C / Inert atmosphere

3.1: potassium hexamethylsilazane / tetrahydrofuran; toluene / 0.5 h / -78 °C / Inert atmosphere

3.2: -78 - 20 °C / Inert atmosphere

With oxalyl dichloride; potassium hexamethylsilazane; diisobutylaluminium hydride; dimethyl sulfoxide; In tetrahydrofuran; dichloromethane; toluene;

DOI:10.1021/ol202829u

upstream raw materials:

(2S,3R)-3-(tert-butyldimethylsilanyloxy)-2-methylbutyraldehyde

methyl 2R,3R-nilate

tert-butyldimethylsilyl chloride

(2R,3R)-3-<(tert-Butyl)dimethylsilyloxy>-2-methylbuttersaeure-methylester