anti-(2R,3R)-2-[E-2-(2-bromo-5-methoxyphenyl)-ethenyl]-1-[(2S,4R)-2-(tert-butyldiphenylsilyloxymethyl)-4-methoxymethyloxy-pyrrolidin-1-yl]-3-(3-tert-butyldiphenylsilyloxypropyl)-4-methyl-4-pentene-1-one

Base Information

• Chemical Name: anti-(2R,3R)-2-[E-2-(2-bromo-5-methoxyphenyl)-ethenyl]-1-[(2S,4R)-2-(tert-butyldiphenylsilyloxymethyl)-4-methoxymethyloxy-pyrrolidin-1-yl]-3-(3-tert-butyldiphenylsilyloxypropyl)-4-methyl-4-pentene-1-one
• CAS No.: 1380512-04-8
• Molecular Formula: C₅₇H₇₂BrNO₆Si₂
• Molecular Weight: 1003.28
• Mol file: 1380512-04-8.mol

Synonyms:

Chemical Property of anti-(2R,3R)-2-[E-2-(2-bromo-5-methoxyphenyl)-ethenyl]-1-[(2S,4R)-2-(tert-butyldiphenylsilyloxymethyl)-4-methoxymethyloxy-pyrrolidin-1-yl]-3-(3-tert-butyldiphenylsilyloxypropyl)-4-methyl-4-pentene-1-one

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of anti-(2R,3R)-2-[E-2-(2-bromo-5-methoxyphenyl)-ethenyl]-1-[(2S,4R)-2-(tert-butyldiphenylsilyloxymethyl)-4-methoxymethyloxy-pyrrolidin-1-yl]-3-(3-tert-butyldiphenylsilyloxypropyl)-4-methyl-4-pentene-1-one

There total 10 articles about anti-(2R,3R)-2-[E-2-(2-bromo-5-methoxyphenyl)-ethenyl]-1-[(2S,4R)-2-(tert-butyldiphenylsilyloxymethyl)-4-methoxymethyloxy-pyrrolidin-1-yl]-3-(3-tert-butyldiphenylsilyloxypropyl)-4-methyl-4-pentene-1-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:

(E)-4-(2-bromo-5-methoxyphenyl)-but-3-enoyl fluoride (1380511-98-7) + (2S,4R)-1-[(E)-6-(tert-butyldiphenylsilyloxy)-2-methyl-hex-2-enyl]-2-(tert-butyldiphenylsilyloxymethyl)-4-(methoxymethyloxy)pyrrolidine (1380511-85-2) → anti-(2R,3R)-2-[E-2-(2-bromo-5-methoxyphenyl)-ethenyl]-1-[(2S,4R)-2-(tert-butyldiphenylsilyloxymethyl)-4-methoxymethyloxy-pyrrolidin-1-yl]-3-(3-tert-butyldiphenylsilyloxypropyl)-4-methyl-4-pentene-1-one (1380512-04-8) + anti-(2S,3S)-2-[E-2-(2-bromo-5-methoxyphenyl)-ethenyl]-1-[(2S,4R)-2-(tert-butyldiphenylsilyloxymethyl)-4-methoxymethyloxy-pyrrolidin-1-yl]-3-(3-tert-butyldiphenylsilyloxypropyl)-4-methyl-4-pentene-1-one (1380512-05-9)

Guidance literature:

(E)-4-(2-bromo-5-methoxyphenyl)-but-3-enoyl fluoride; (2S,4R)-1-[(E)-6-(tert-butyldiphenylsilyloxy)-2-methyl-hex-2-enyl]-2-(tert-butyldiphenylsilyloxymethyl)-4-(methoxymethyloxy)pyrrolidine; With trimethylaluminum; sodium carbonate; In dichloromethane; toluene; at 0 ℃; for 6h; Inert atmosphere;

With water; In dichloromethane; toluene; at 20 ℃; for 0.25h; optical yield given as %de; diastereoselective reaction; Inert atmosphere;

DOI:10.1002/ejoc.201200073

Reference yield:

6-((tert-butyldiphenylsilyl)oxy)-2-methylhex-1-en-3-ol (906724-01-4) → anti-(2R,3R)-2-[E-2-(2-bromo-5-methoxyphenyl)-ethenyl]-1-[(2S,4R)-2-(tert-butyldiphenylsilyloxymethyl)-4-methoxymethyloxy-pyrrolidin-1-yl]-3-(3-tert-butyldiphenylsilyloxypropyl)-4-methyl-4-pentene-1-one (1380512-04-8) + anti-(2S,3S)-2-[E-2-(2-bromo-5-methoxyphenyl)-ethenyl]-1-[(2S,4R)-2-(tert-butyldiphenylsilyloxymethyl)-4-methoxymethyloxy-pyrrolidin-1-yl]-3-(3-tert-butyldiphenylsilyloxypropyl)-4-methyl-4-pentene-1-one (1380512-05-9)

Guidance literature:

Multi-step reaction with 6 steps

1.1: pyridine; N-ethyl-N,N-diisopropylamine / dichloromethane; acetonitrile / 3 h / -15 - 20 °C / Inert atmosphere

2.1: tris(dibenzylideneacetone)dipalladium⁽⁰⁾ chloroform complex; triethylamine; triphenylphosphine / tetrahydrofuran; acetonitrile / 24 h / 20 °C / Inert atmosphere

3.1: dmap; N-ethyl-N,N-diisopropylamine / dichloromethane / 168 h / 0 - 20 °C / Inert atmosphere; Reflux

3.2: 3 h / Inert atmosphere

4.1: diisobutylaluminium hydride / tetrahydrofuran; toluene / 0 - 20 °C / Inert atmosphere

4.2: Inert atmosphere

5.1: 1H-imidazole / dichloromethane / 3 h / 20 °C / Inert atmosphere

6.1: trimethylaluminum; sodium carbonate / dichloromethane; toluene / 6 h / 0 °C / Inert atmosphere

6.2: 0.25 h / 20 °C / Inert atmosphere

With pyridine; 1H-imidazole; dmap; tris(dibenzylideneacetone)dipalladium⁽⁰⁾ chloroform complex; trimethylaluminum; diisobutylaluminium hydride; sodium carbonate; triethylamine; N-ethyl-N,N-diisopropylamine; triphenylphosphine; In tetrahydrofuran; dichloromethane; toluene; acetonitrile; 6.2: Aza-Claisen rearrangement;

DOI:10.1002/ejoc.201200073

Reference yield:

tert-butylchlorodiphenylsilane (58479-61-1) → anti-(2R,3R)-2-[E-2-(2-bromo-5-methoxyphenyl)-ethenyl]-1-[(2S,4R)-2-(tert-butyldiphenylsilyloxymethyl)-4-methoxymethyloxy-pyrrolidin-1-yl]-3-(3-tert-butyldiphenylsilyloxypropyl)-4-methyl-4-pentene-1-one (1380512-04-8) + anti-(2S,3S)-2-[E-2-(2-bromo-5-methoxyphenyl)-ethenyl]-1-[(2S,4R)-2-(tert-butyldiphenylsilyloxymethyl)-4-methoxymethyloxy-pyrrolidin-1-yl]-3-(3-tert-butyldiphenylsilyloxypropyl)-4-methyl-4-pentene-1-one (1380512-05-9)

Guidance literature:

Multi-step reaction with 9 steps

1.1: N-ethyl-N,N-diisopropylamine / dichloromethane / 2 h / 20 °C / Inert atmosphere

2.1: sodium hypochlorite; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; sodium hydrogencarbonate; potassium bromide / dichloromethane; water / Inert atmosphere; Cooling with ice

3.1: bromine; magnesium / tetrahydrofuran / 1 h / 20 °C / Inert atmosphere

3.2: 20 °C / Inert atmosphere

3.3: 0 °C

4.1: pyridine; N-ethyl-N,N-diisopropylamine / dichloromethane; acetonitrile / 3 h / -15 - 20 °C / Inert atmosphere

5.1: tris(dibenzylideneacetone)dipalladium⁽⁰⁾ chloroform complex; triethylamine; triphenylphosphine / tetrahydrofuran; acetonitrile / 24 h / 20 °C / Inert atmosphere

6.1: dmap; N-ethyl-N,N-diisopropylamine / dichloromethane / 168 h / 0 - 20 °C / Inert atmosphere; Reflux

6.2: 3 h / Inert atmosphere

7.1: diisobutylaluminium hydride / tetrahydrofuran; toluene / 0 - 20 °C / Inert atmosphere

7.2: Inert atmosphere

8.1: 1H-imidazole / dichloromethane / 3 h / 20 °C / Inert atmosphere

9.1: trimethylaluminum; sodium carbonate / dichloromethane; toluene / 6 h / 0 °C / Inert atmosphere

9.2: 0.25 h / 20 °C / Inert atmosphere

With pyridine; 1H-imidazole; dmap; tris(dibenzylideneacetone)dipalladium⁽⁰⁾ chloroform complex; sodium hypochlorite; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; bromine; trimethylaluminum; diisobutylaluminium hydride; sodium hydrogencarbonate; sodium carbonate; magnesium; triethylamine; N-ethyl-N,N-diisopropylamine; triphenylphosphine; potassium bromide; In tetrahydrofuran; dichloromethane; water; toluene; acetonitrile; 9.2: Aza-Claisen rearrangement;

DOI:10.1002/ejoc.201200073

upstream raw materials:

methyl (2S,4R)-1-[(E)-6-tert-butyldiphenylsilyloxy-2-methylhex-2-enyl]-4-hydroxypyrrolidine-2-carboxylate

methyl (2S,4R)-1-[(E)-6-tert-butyldiphenylsilyloxy-2-methylhex-2-enyl]-4-(methoxymethyloxy)-pyrrolidine-2-carboxylate

(2S,4R)-1-[(E)-6-[(tert-butyldiphenylsilyl)oxy]-2-methylhex-2-en-1-yl]-2-hydroxymethyl-4-(methoxymethoxy)pyrrolidine

(E)-4-(2-bromo-5-methoxyphenyl)-but-3-enoyl fluoride