(3R,4S)-5-(tert-Butyl-diphenyl-silanyloxy)-4-methoxymethoxy-3-phenyl-pentanoic acid ethyl ester

Base Information

• Chemical Name: (3R,4S)-5-(tert-Butyl-diphenyl-silanyloxy)-4-methoxymethoxy-3-phenyl-pentanoic acid ethyl ester
• CAS No.: 861222-41-5
• Molecular Formula: C₃₁H₄₀O₅Si
• Molecular Weight: 520.741
• Mol file: 861222-41-5.mol

Synonyms:(3R,4S)-5-(tert-Butyl-diphenyl-silanyloxy)-4-methoxymethoxy-3-phenyl-pentanoic acid ethyl ester

Chemical Property of (3R,4S)-5-(tert-Butyl-diphenyl-silanyloxy)-4-methoxymethoxy-3-phenyl-pentanoic acid ethyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (3R,4S)-5-(tert-Butyl-diphenyl-silanyloxy)-4-methoxymethoxy-3-phenyl-pentanoic acid ethyl ester

There total 4 articles about (3R,4S)-5-(tert-Butyl-diphenyl-silanyloxy)-4-methoxymethoxy-3-phenyl-pentanoic acid ethyl ester 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: 80.0%

ethyl (2E,4S)-5-(tert-butyldiphenylsilanyloxy)-4-(methoxymethyloxy)-2-pentenoate (861222-40-4) + bromobenzene (108-86-1,52753-63-6) → (3R,4S)-5-(tert-Butyl-diphenyl-silanyloxy)-4-methoxymethoxy-3-phenyl-pentanoic acid ethyl ester (861222-41-5)

Guidance literature:

bromobenzene; With copper(l) iodide; magnesium; In tetrahydrofuran; at -78 ℃; for 0.666667h;

ethyl (2E,4S)-5-(tert-butyldiphenylsilanyloxy)-4-(methoxymethyloxy)-2-pentenoate; With chloro-trimethyl-silane; In tetrahydrofuran; at -78 - 20 ℃;

DOI:10.1016/j.tetlet.2005.05.006

Reference yield:

ethyl (2E,4S)-5-(tert-butyldiphenylsilanyloxy)-4-hydroxy-2-pentenoate (885051-17-2) → (3R,4S)-5-(tert-Butyl-diphenyl-silanyloxy)-4-methoxymethoxy-3-phenyl-pentanoic acid ethyl ester (861222-41-5)

Guidance literature:

Multi-step reaction with 2 steps

1.1: 85 percent / i-Pr₂NEt / CH₂Cl₂ / 0 - 20 °C

2.1: Mg / tetrahydrofuran / Heating

2.2: CuI / tetrahydrofuran / 0.67 h / -78 °C

2.3: 80 percent / Me₃SiCl / tetrahydrofuran / -78 - 20 °C

With magnesium; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; dichloromethane;

DOI:10.1021/jo052383v

Reference yield:

ethyl (E)-3-((S)-2,2-dimethyl-1,3-dioxolan-4-yl)acrylate (64520-58-7,917877-01-1) → (3R,4S)-5-(tert-Butyl-diphenyl-silanyloxy)-4-methoxymethoxy-3-phenyl-pentanoic acid ethyl ester (861222-41-5)

Guidance literature:

Multi-step reaction with 4 steps

1.1: acetic acid / H₂O / 20 h / 20 °C

2.1: 7.0 g / DMAP; imidazole / dimethylformamide / 20 °C

3.1: 85 percent / i-Pr₂NEt / CH₂Cl₂ / 0 - 20 °C

4.1: Mg / tetrahydrofuran / Heating

4.2: CuI / tetrahydrofuran / 0.67 h / -78 °C

4.3: 80 percent / Me₃SiCl / tetrahydrofuran / -78 - 20 °C

With 1H-imidazole; dmap; magnesium; acetic acid; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; dichloromethane; water; N,N-dimethyl-formamide;

DOI:10.1021/jo052383v

upstream raw materials:

ethyl (2E,4S)-5-(tert-butyldiphenylsilanyloxy)-4-(methoxymethyloxy)-2-pentenoate

bromobenzene

ethyl (2E,4S)-5-(tert-butyldiphenylsilanyloxy)-4-hydroxy-2-pentenoate

ethyl (E)-3-((S)-2,2-dimethyl-1,3-dioxolan-4-yl)acrylate

Downstream raw materials:

(4S,5R)-5-(hydroxymethyl)-4-phenyldihydrofuran-2(3H)-one

(4R,5S)-5-((tert-butyldiphenylsilyloxy)methyl)-4-benzyldihydrofuran-2(3H)-one