anti-(2R,3S)-1-[(2S,4R)-4-tert-butoxy-2-phenoxymethyl-pyrrolidin-1-yl]-3-(3-tert-butyldiphenylsilyloxypropyl)-2-[E-2-(3-methoxyphenyl)-ethenyl]-4-methyl-4-pentene-1-one

Base Information

• Chemical Name: anti-(2R,3S)-1-[(2S,4R)-4-tert-butoxy-2-phenoxymethyl-pyrrolidin-1-yl]-3-(3-tert-butyldiphenylsilyloxypropyl)-2-[E-2-(3-methoxyphenyl)-ethenyl]-4-methyl-4-pentene-1-one
• CAS No.: 1380512-39-9
• Molecular Formula: C₄₉H₆₃NO₅Si
• Molecular Weight: 774.128

Synonyms:

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
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MSDS Files:

Useful:

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

There total 10 articles about anti-(2R,3S)-1-[(2S,4R)-4-tert-butoxy-2-phenoxymethyl-pyrrolidin-1-yl]-3-(3-tert-butyldiphenylsilyloxypropyl)-2-[E-2-(3-methoxyphenyl)-ethenyl]-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:

(2S,4R)-1-[(E)-6-(tert-butyldiphenylsilyloxy)-2-methyl-hex-2-enyl]-4-(tert-butoxy)-2-(phenoxymethyl)pyrrolidine (1380511-91-0) + E-4-(3-methoxyphenyl)-3-butenoyl fluoride → anti-(2S,3S)-1-[(2S,4R)-4-tert-butoxy-2-phenoxymethyl-pyrrolidin-1-yl]-3-(3-tert-butyldiphenylsilyloxypropyl)-2-[E-2-(3-methoxyphenyl)-ethenyl]-4-methyl-4-pentene-1-one (1380512-37-7) + anti-(2R,3S)-1-[(2S,4R)-4-tert-butoxy-2-phenoxymethyl-pyrrolidin-1-yl]-3-(3-tert-butyldiphenylsilyloxypropyl)-2-[E-2-(3-methoxyphenyl)-ethenyl]-4-methyl-4-pentene-1-one (1380512-39-9) + anti-(2S,3R)-1-[(2S,4R)-4-tert-butoxy-2-phenoxymethyl-pyrrolidin-1-yl]-3-(3-tert-butyldiphenylsilyloxypropyl)-2-[E-2-(3-methoxyphenyl)-ethenyl]-4-methyl-4-pentene-1-one (1380512-41-3) + anti-(2R,3R)-1-[(2S,4R)-4-tert-butoxy-2-phenoxymethyl-pyrrolidin-1-yl]-3-(3-tert-butyldiphenylsilyloxypropyl)-2-[E-2-(3-methoxyphenyl)-ethenyl]-4-methyl-4-pentene-1-one (1380512-35-5)

Guidance literature:

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

With water; In dichloromethane; toluene; at 20 ℃; for 0.25h; diastereoselective reaction; Inert atmosphere;

DOI:10.1002/ejoc.201200073

Reference yield:

(2S,4R)-N-(benzyloxycarbonyl)-4-tert-butoxy-2-(phenoxymethyl)pyrrolidine (1380511-76-1) → anti-(2S,3S)-1-[(2S,4R)-4-tert-butoxy-2-phenoxymethyl-pyrrolidin-1-yl]-3-(3-tert-butyldiphenylsilyloxypropyl)-2-[E-2-(3-methoxyphenyl)-ethenyl]-4-methyl-4-pentene-1-one (1380512-37-7) + anti-(2R,3S)-1-[(2S,4R)-4-tert-butoxy-2-phenoxymethyl-pyrrolidin-1-yl]-3-(3-tert-butyldiphenylsilyloxypropyl)-2-[E-2-(3-methoxyphenyl)-ethenyl]-4-methyl-4-pentene-1-one (1380512-39-9) + anti-(2S,3R)-1-[(2S,4R)-4-tert-butoxy-2-phenoxymethyl-pyrrolidin-1-yl]-3-(3-tert-butyldiphenylsilyloxypropyl)-2-[E-2-(3-methoxyphenyl)-ethenyl]-4-methyl-4-pentene-1-one (1380512-41-3)

Guidance literature:

Multi-step reaction with 3 steps

1.1: palladium 10% on activated carbon; hydrogen / ethyl acetate / 264 h

2.1: tris(dibenzylideneacetone)dipalladium⁽⁰⁾ chloroform complex; N-ethyl-N,N-diisopropylamine; triphenylphosphine / acetonitrile / 20 h / 20 °C / Inert atmosphere

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

3.2: 0.25 h / 20 °C / Inert atmosphere

With tris(dibenzylideneacetone)dipalladium⁽⁰⁾ chloroform complex; palladium 10% on activated carbon; hydrogen; trimethylaluminum; sodium carbonate; N-ethyl-N,N-diisopropylamine; triphenylphosphine; In dichloromethane; ethyl acetate; toluene; acetonitrile; 3.2: Aza-Claisen rearrangement;

DOI:10.1002/ejoc.201200073

Reference yield:

(2S,4R)-4-tert-butoxy-2-(phenoxymethyl)pyrrolidine (1380511-77-2) → anti-(2S,3S)-1-[(2S,4R)-4-tert-butoxy-2-phenoxymethyl-pyrrolidin-1-yl]-3-(3-tert-butyldiphenylsilyloxypropyl)-2-[E-2-(3-methoxyphenyl)-ethenyl]-4-methyl-4-pentene-1-one (1380512-37-7) + anti-(2R,3S)-1-[(2S,4R)-4-tert-butoxy-2-phenoxymethyl-pyrrolidin-1-yl]-3-(3-tert-butyldiphenylsilyloxypropyl)-2-[E-2-(3-methoxyphenyl)-ethenyl]-4-methyl-4-pentene-1-one (1380512-39-9) + anti-(2S,3R)-1-[(2S,4R)-4-tert-butoxy-2-phenoxymethyl-pyrrolidin-1-yl]-3-(3-tert-butyldiphenylsilyloxypropyl)-2-[E-2-(3-methoxyphenyl)-ethenyl]-4-methyl-4-pentene-1-one (1380512-41-3)

Guidance literature:

Multi-step reaction with 2 steps

1.1: tris(dibenzylideneacetone)dipalladium⁽⁰⁾ chloroform complex; N-ethyl-N,N-diisopropylamine; triphenylphosphine / acetonitrile / 20 h / 20 °C / Inert atmosphere

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

2.2: 0.25 h / 20 °C / Inert atmosphere

With tris(dibenzylideneacetone)dipalladium⁽⁰⁾ chloroform complex; trimethylaluminum; sodium carbonate; N-ethyl-N,N-diisopropylamine; triphenylphosphine; In dichloromethane; toluene; acetonitrile; 2.2: Aza-Claisen rearrangement;

DOI:10.1002/ejoc.201200073

upstream raw materials:

(2S,4R)-N-(benzyloxycarbonyl)-4-tert-butoxy-2-(hydroxymethyl)pyrrolidine

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

(2S,4R)-N-(benzyloxycarbonyl)-4-tert-butoxy-2-(phenoxymethyl)pyrrolidine

(2S,4R)-4-tert-butoxy-2-(phenoxymethyl)pyrrolidine

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