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

Base Information

Chemical Name:anti-(2R,3R)-1-3-(3-tert-butyldiphenylsilyloxypropyl)-1-[(2S,5S)-2,5-di(methoxymethyl)-pyrrolidin-1-yl]-2-[E-2-(3-methoxyphenyl)ethenyl]-4-methyl-4-pentene-1-one
CAS No.:1380512-43-5
Molecular Formula:C₄₂H₅₇NO₅Si
Molecular Weight:684.004
Hs Code.:

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

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

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

There total 6 articles about anti-(2R,3R)-1-3-(3-tert-butyldiphenylsilyloxypropyl)-1-[(2S,5S)-2,5-di(methoxymethyl)-pyrrolidin-1-yl]-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:

: 1380511-92-1
(2S,5S)-1-[(E)-6-(tert-butyldiphenylsilyloxy)-2-methyl-hex-2-enyl]-2,5-bis(methoxymethyl)pyrrolidine

: E-4-(3-methoxyphenyl)-3-butenoyl fluoride

: 1380512-45-7
anti-(2S,3S)-1-3-(3-tert-butyldiphenylsilyloxypropyl)-1-[(2S,5S)-2,5-di(methoxymethyl)-pyrrolidin-1-yl]-2-[E-2-(3-methoxyphenyl)ethenyl]-4-methyl-4-pentene-1-one

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

: 1380512-43-5
anti-(2R,3R)-1-3-(3-tert-butyldiphenylsilyloxypropyl)-1-[(2S,5S)-2,5-di(methoxymethyl)-pyrrolidin-1-yl]-2-[E-2-(3-methoxyphenyl)ethenyl]-4-methyl-4-pentene-1-one

Guidance literature:: (2S,5S)-1-[(E)-6-(tert-butyldiphenylsilyloxy)-2-methyl-hex-2-enyl]-2,5-bis(methoxymethyl)pyrrolidine; E-4-(3-methoxyphenyl)-3-butenoyl fluoride; With trimethylaluminum; sodium carbonate; In dichloromethane; toluene; at -20 ℃; 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:

: C₂₄H₃₄O₄SSi

: 1380512-43-5
anti-(2R,3R)-1-3-(3-tert-butyldiphenylsilyloxypropyl)-1-[(2S,5S)-2,5-di(methoxymethyl)-pyrrolidin-1-yl]-2-[E-2-(3-methoxyphenyl)ethenyl]-4-methyl-4-pentene-1-one

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 / -20 °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

Reference yield:

: 127793-62-8
4-((tert-butyldiphenylsilyl)oxy)butanal

: 1380512-43-5
anti-(2R,3R)-1-3-(3-tert-butyldiphenylsilyloxypropyl)-1-[(2S,5S)-2,5-di(methoxymethyl)-pyrrolidin-1-yl]-2-[E-2-(3-methoxyphenyl)ethenyl]-4-methyl-4-pentene-1-one

Guidance literature:: Multi-step reaction with 4 steps

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

1.2: 20 °C / Inert atmosphere

1.3: 0 °C

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

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

4.1: trimethylaluminum; sodium carbonate / dichloromethane; toluene / 6 h / -20 °C / Inert atmosphere

4.2: 0.25 h / 20 °C / Inert atmosphere

With pyridine; tris(dibenzylideneacetone)dipalladium⁽⁰⁾ chloroform complex; bromine; trimethylaluminum; sodium carbonate; magnesium; N-ethyl-N,N-diisopropylamine; triphenylphosphine; In tetrahydrofuran; dichloromethane; toluene; acetonitrile; 4.2: Aza-Claisen rearrangement;
DOI:10.1002/ejoc.201200073