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

Base Information

Chemical Name:anti-(2R,3R)-1-[(2S)-2-(tert-butyldimethylsilyloxymethyl)-pyrrolidin-1-yl]-3-(3-tert-butyldiphenylsilyloxypropyl)-2-[E-2-(3-methoxyphenyl)-ethyl]-4-methyl-4-pentene-1-one
CAS No.:1380512-53-7
Molecular Formula:C₄₅H₆₇NO₄Si₂
Molecular Weight:742.202
Hs Code.:

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

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

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

There total 5 articles about anti-(2R,3R)-1-[(2S)-2-(tert-butyldimethylsilyloxymethyl)-pyrrolidin-1-yl]-3-(3-tert-butyldiphenylsilyloxypropyl)-2-[E-2-(3-methoxyphenyl)-ethyl]-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: 63.2%

: 1380512-03-7
anti-(2R,3R)-1-[(2S)-2-(tert-butyldimethylsilyloxymethyl)pyrrolidin-1-yl]-3-(3-tert-butyldiphenylsilyloxypropyl)-2-[E-2-(3-methoxyphenyl)ethenyl]-4-methyl-4-pentene-1-one

: 1380512-53-7
anti-(2R,3R)-1-[(2S)-2-(tert-butyldimethylsilyloxymethyl)-pyrrolidin-1-yl]-3-(3-tert-butyldiphenylsilyloxypropyl)-2-[E-2-(3-methoxyphenyl)-ethyl]-4-methyl-4-pentene-1-one

Guidance literature:: With palladium on activated charcoal; hydrogen; In ethyl acetate; for 24h;
DOI:10.1002/ejoc.201200073

Reference yield:

: 1380511-82-9
(2S)-1-[(E)-6-(tert-butyldiphenylsilyloxy)-2-methylhex-2-enyl]-2-(hydroxymethyl)pyrrolidine

: 1380512-53-7
anti-(2R,3R)-1-[(2S)-2-(tert-butyldimethylsilyloxymethyl)-pyrrolidin-1-yl]-3-(3-tert-butyldiphenylsilyloxypropyl)-2-[E-2-(3-methoxyphenyl)-ethyl]-4-methyl-4-pentene-1-one

Guidance literature:: Multi-step reaction with 3 steps

1.1: triethylamine / N,N-dimethyl-formamide / 0 - 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

3.1: palladium on activated charcoal; hydrogen / ethyl acetate / 24 h

With palladium on activated charcoal; hydrogen; trimethylaluminum; sodium carbonate; triethylamine; In dichloromethane; ethyl acetate; N,N-dimethyl-formamide; toluene; 2.2: Aza-Claisen rearrangement;
DOI:10.1002/ejoc.201200073

Reference yield:

: 1380511-83-0
(2S)-1-[(E)-6-(tert-butyldiphenylsilyloxy)-2-methylhex-2-enyl]-2-(tert-butyldimethylsilyloxymethyl)pyrrolidine

: 1380512-53-7
anti-(2R,3R)-1-[(2S)-2-(tert-butyldimethylsilyloxymethyl)-pyrrolidin-1-yl]-3-(3-tert-butyldiphenylsilyloxypropyl)-2-[E-2-(3-methoxyphenyl)-ethyl]-4-methyl-4-pentene-1-one

Guidance literature:: Multi-step reaction with 2 steps

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

1.2: 0.25 h / 20 °C / Inert atmosphere

2.1: palladium on activated charcoal; hydrogen / ethyl acetate / 24 h

With palladium on activated charcoal; hydrogen; trimethylaluminum; sodium carbonate; In dichloromethane; ethyl acetate; toluene; 1.2: Aza-Claisen rearrangement;
DOI:10.1002/ejoc.201200073