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

Base Information

• Chemical Name: (2S,4R)-1-[(E)-6-(tert-butyldiphenylsilyloxy)-2-methyl-hex-2-enyl]-4-(methoxymethyloxy)-2-(methoxymethoxymethyl)pyrrolidine
• CAS No.: 1380511-86-3
• Molecular Formula: C₃₂H₄₉NO₅Si
• Molecular Weight: 555.83

Synonyms:(2S,4R)-1-[(E)-6-(tert-butyldiphenylsilyloxy)-2-methyl-hex-2-enyl]-4-(methoxymethyloxy)-2-(methoxymethoxymethyl)pyrrolidine

Chemical Property of (2S,4R)-1-[(E)-6-(tert-butyldiphenylsilyloxy)-2-methyl-hex-2-enyl]-4-(methoxymethyloxy)-2-(methoxymethoxymethyl)pyrrolidine

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2S,4R)-1-[(E)-6-(tert-butyldiphenylsilyloxy)-2-methyl-hex-2-enyl]-4-(methoxymethyloxy)-2-(methoxymethoxymethyl)pyrrolidine

There total 8 articles about (2S,4R)-1-[(E)-6-(tert-butyldiphenylsilyloxy)-2-methyl-hex-2-enyl]-4-(methoxymethyloxy)-2-(methoxymethoxymethyl)pyrrolidine 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: 46.0%

(2S,4R)-1-[(E)-6-[(tert-butyldiphenylsilyl)oxy]-2-methylhex-2-en-1-yl]-2-hydroxymethyl-4-(methoxymethoxy)pyrrolidine (1380511-84-1) + chloromethyl methyl ether (107-30-2) → (2S,4R)-1-[(E)-6-(tert-butyldiphenylsilyloxy)-2-methyl-hex-2-enyl]-4-(methoxymethyloxy)-2-(methoxymethoxymethyl)pyrrolidine (1380511-86-3)

Guidance literature:

(2S,4R)-1-[(E)-6-[(tert-butyldiphenylsilyl)oxy]-2-methylhex-2-en-1-yl]-2-hydroxymethyl-4-(methoxymethoxy)pyrrolidine; chloromethyl methyl ether; With dmap; N-ethyl-N,N-diisopropylamine; In dichloromethane; at 0 - 20 ℃; for 96h; Inert atmosphere;

With sodium carbonate; In dichloromethane; water; for 9h; Inert atmosphere;

DOI:10.1002/ejoc.201200073

Reference yield:

methyl (2S,4R)-1-[(E)-6-tert-butyldiphenylsilyloxy-2-methylhex-2-enyl]-4-hydroxypyrrolidine-2-carboxylate (1380511-79-4) → (2S,4R)-1-[(E)-6-(tert-butyldiphenylsilyloxy)-2-methyl-hex-2-enyl]-4-(methoxymethyloxy)-2-(methoxymethoxymethyl)pyrrolidine (1380511-86-3)

Guidance literature:

Multi-step reaction with 3 steps

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

1.2: 3 h / Inert atmosphere

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

2.2: Inert atmosphere

3.1: dmap; N-ethyl-N,N-diisopropylamine / dichloromethane / 96 h / 0 - 20 °C / Inert atmosphere

3.2: 9 h / Inert atmosphere

With dmap; diisobutylaluminium hydride; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; dichloromethane; toluene;

DOI:10.1002/ejoc.201200073

Reference yield:

C24H34O4SSi → (2S,4R)-1-[(E)-6-(tert-butyldiphenylsilyloxy)-2-methyl-hex-2-enyl]-4-(methoxymethyloxy)-2-(methoxymethoxymethyl)pyrrolidine (1380511-86-3)

Guidance literature:

Multi-step reaction with 4 steps

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

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

2.2: 3 h / Inert atmosphere

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

3.2: Inert atmosphere

4.1: dmap; N-ethyl-N,N-diisopropylamine / dichloromethane / 96 h / 0 - 20 °C / Inert atmosphere

4.2: 9 h / Inert atmosphere

With dmap; tris(dibenzylideneacetone)dipalladium⁽⁰⁾ chloroform complex; diisobutylaluminium hydride; triethylamine; N-ethyl-N,N-diisopropylamine; triphenylphosphine; In tetrahydrofuran; dichloromethane; toluene; acetonitrile;

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

chloromethyl methyl ether

Downstream raw materials:

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

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

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