(3S,4R,E)-methyl 3-(tert-butyldimethylsilyloxy)-4-methyl-6-phenylhex-5-enoate

Base Information

• Chemical Name: (3S,4R,E)-methyl 3-(tert-butyldimethylsilyloxy)-4-methyl-6-phenylhex-5-enoate
• CAS No.: 1609178-45-1
• Molecular Formula: C₂₀H₃₂O₃Si
• Molecular Weight: 348.558
• Mol file: 1609178-45-1.mol

Synonyms:(3S,4R,E)-methyl 3-(tert-butyldimethylsilyloxy)-4-methyl-6-phenylhex-5-enoate

Chemical Property of (3S,4R,E)-methyl 3-(tert-butyldimethylsilyloxy)-4-methyl-6-phenylhex-5-enoate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (3S,4R,E)-methyl 3-(tert-butyldimethylsilyloxy)-4-methyl-6-phenylhex-5-enoate

There total 3 articles about (3S,4R,E)-methyl 3-(tert-butyldimethylsilyloxy)-4-methyl-6-phenylhex-5-enoate 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: 93.0%

(3S,4R,E)-methyl 3-hydroxy-4-methyl-6-phenylhex-5-enoate (1609178-44-0) + tert-butyldimethylsilyl chloride (18162-48-6) → (3S,4R,E)-methyl 3-(tert-butyldimethylsilyloxy)-4-methyl-6-phenylhex-5-enoate (1609178-45-1)

Guidance literature:

With 1H-imidazole; In N,N-dimethyl-formamide; at 0 - 20 ℃; for 2.25h;

DOI:10.1016/j.tetasy.2014.03.011

Reference yield:

(S)-2-((S)-5,5-dimethyl-4,6-dioxaspiro[2.5]octan-7-yl)propanal (1609178-42-8) → (3S,4R,E)-methyl 3-(tert-butyldimethylsilyloxy)-4-methyl-6-phenylhex-5-enoate (1609178-45-1)

Guidance literature:

Multi-step reaction with 3 steps

1.1: n-butyllithium / tetrahydrofuran / 3 h / -78 °C / Inert atmosphere

2.1: pyridinium p-toluenesulfonate / 0.33 h / Reflux

2.2: 0.5 h / 20 °C

3.1: 1H-imidazole / N,N-dimethyl-formamide / 2.25 h / 0 - 20 °C

With 1H-imidazole; n-butyllithium; pyridinium p-toluenesulfonate; In tetrahydrofuran; N,N-dimethyl-formamide; 1.1: |Horner-Wadsworth-Emmons Olefination;

DOI:10.1016/j.tetasy.2014.03.011

Reference yield:

(S)-5,5-dimethyl-7-((R,E)-4-phenylbut-3-en-2-yl)-4,6-dioxaspiro[2.5]octane (1609178-43-9) → (3S,4R,E)-methyl 3-(tert-butyldimethylsilyloxy)-4-methyl-6-phenylhex-5-enoate (1609178-45-1)

Guidance literature:

Multi-step reaction with 2 steps

1.1: pyridinium p-toluenesulfonate / 0.33 h / Reflux

1.2: 0.5 h / 20 °C

2.1: 1H-imidazole / N,N-dimethyl-formamide / 2.25 h / 0 - 20 °C

With 1H-imidazole; pyridinium p-toluenesulfonate; In N,N-dimethyl-formamide;

DOI:10.1016/j.tetasy.2014.03.011

upstream raw materials:

(S)-2-((S)-5,5-dimethyl-4,6-dioxaspiro[2.5]octan-7-yl)propanal

(S)-5,5-dimethyl-7-((R,E)-4-phenylbut-3-en-2-yl)-4,6-dioxaspiro[2.5]octane

(3S,4R,E)-methyl 3-hydroxy-4-methyl-6-phenylhex-5-enoate

tert-butyldimethylsilyl chloride

Downstream raw materials:

(3S,4R,5E)-3-[(tert-butyldimethylsilyl)oxy]-4-methyl-6-phenyl-5-hexenal

(2E,5S,6R,7E)-ethyl 5-hydroxy-6-methyl-8-phenylocta-2,7-dienoate