tert-butyl (2R,5R,3E)-5-[N-(tert-butoxycarbonyl)amino]-2-[3-(tert-butyldimethylsiloxy)propyl]-6-(4-methoxyphenyl)hex-3-enoate

Base Information

Chemical Name:tert-butyl (2R,5R,3E)-5-[N-(tert-butoxycarbonyl)amino]-2-[3-(tert-butyldimethylsiloxy)propyl]-6-(4-methoxyphenyl)hex-3-enoate
CAS No.:1361407-57-9
Molecular Formula:C₃₁H₅₃NO₆Si
Molecular Weight:563.85
Hs Code.:

Synonyms:tert-butyl (2R,5R,3E)-5-[N-(tert-butoxycarbonyl)amino]-2-[3-(tert-butyldimethylsiloxy)propyl]-6-(4-methoxyphenyl)hex-3-enoate

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Chemical Property of tert-butyl (2R,5R,3E)-5-[N-(tert-butoxycarbonyl)amino]-2-[3-(tert-butyldimethylsiloxy)propyl]-6-(4-methoxyphenyl)hex-3-enoate

Chemical Property:

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Technology Process of tert-butyl (2R,5R,3E)-5-[N-(tert-butoxycarbonyl)amino]-2-[3-(tert-butyldimethylsiloxy)propyl]-6-(4-methoxyphenyl)hex-3-enoate

There total 7 articles about tert-butyl (2R,5R,3E)-5-[N-(tert-butoxycarbonyl)amino]-2-[3-(tert-butyldimethylsiloxy)propyl]-6-(4-methoxyphenyl)hex-3-enoate 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: 94.0%

: 1361407-56-8
tert-butyl (4R,5R,2E)-5-[N-(tert-butoxycarbonyl)amino]-4-[(methylsulfonyl)oxy]-6-(4-methoxyphenyl)hex-2-enoate

: 3-(tert-butyldimethylsilyloxy)-1-propyllithium

: 1361407-57-9
tert-butyl (2R,5R,3E)-5-[N-(tert-butoxycarbonyl)amino]-2-[3-(tert-butyldimethylsiloxy)propyl]-6-(4-methoxyphenyl)hex-3-enoate

Guidance literature:: With copper(l) cyanide; lithium chloride; In tetrahydrofuran; diethyl ether; pentane; at -78 - 0 ℃; for 1h; Inert atmosphere;
DOI:10.1021/jm2016914

Reference yield:

: 1361407-53-5
(3R,4R)-4-[N-(tert-butoxycarbonyl)amino]-5-(4-methoxyphenyl)pent-1-en-3-ol

: 1361407-57-9
tert-butyl (2R,5R,3E)-5-[N-(tert-butoxycarbonyl)amino]-2-[3-(tert-butyldimethylsiloxy)propyl]-6-(4-methoxyphenyl)hex-3-enoate

Guidance literature:: Multi-step reaction with 6 steps

1.1: pyridine; dmap / chloroform / 2 h / 0 °C

2.1: dimethylsulfide; ozone / ethyl acetate / 0.5 h / -78 - 0 °C

3.1: N-ethyl-N,N-diisopropylamine; lithium chloride / acetonitrile / 0.33 h / 0 °C / Inert atmosphere

3.2: 3 h / 0 °C / Inert atmosphere

4.1: methanol; potassium carbonate / 2 h / 0 - 20 °C

5.1: triethylamine / dichloromethane / 2 h / 0 °C

6.1: copper(l) cyanide; lithium chloride / tetrahydrofuran; diethyl ether; pentane / 1 h / -78 - 0 °C / Inert atmosphere

With pyridine; methanol; dmap; dimethylsulfide; copper(l) cyanide; potassium carbonate; ozone; triethylamine; N-ethyl-N,N-diisopropylamine; lithium chloride; In tetrahydrofuran; diethyl ether; dichloromethane; chloroform; ethyl acetate; acetonitrile; pentane; 3.1: Horner-Wadsworth-Emmons olefination / 3.2: Horner-Wadsworth-Emmons olefination;
DOI:10.1021/jm2016914

Reference yield:

: C₁₈H₂₅NO₆

: 1361407-57-9
tert-butyl (2R,5R,3E)-5-[N-(tert-butoxycarbonyl)amino]-2-[3-(tert-butyldimethylsiloxy)propyl]-6-(4-methoxyphenyl)hex-3-enoate

Guidance literature:: Multi-step reaction with 4 steps

1.1: N-ethyl-N,N-diisopropylamine; lithium chloride / acetonitrile / 0.33 h / 0 °C / Inert atmosphere

1.2: 3 h / 0 °C / Inert atmosphere

2.1: methanol; potassium carbonate / 2 h / 0 - 20 °C

3.1: triethylamine / dichloromethane / 2 h / 0 °C

4.1: copper(l) cyanide; lithium chloride / tetrahydrofuran; diethyl ether; pentane / 1 h / -78 - 0 °C / Inert atmosphere

With methanol; copper(l) cyanide; potassium carbonate; triethylamine; N-ethyl-N,N-diisopropylamine; lithium chloride; In tetrahydrofuran; diethyl ether; dichloromethane; acetonitrile; pentane; 1.1: Horner-Wadsworth-Emmons olefination / 1.2: Horner-Wadsworth-Emmons olefination;
DOI:10.1021/jm2016914