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

Base Information

Chemical Name:tert-butyl (2S,5R,3Z)-5-[N-(tert-butoxycarbonyl)amino]-2-[3-(tert-butyldimethylsiloxy)-propyl]-6-(4-methoxyphenyl)-3,4-dimethylhex-3-enoate
CAS No.:1361407-76-2
Molecular Formula:C₃₃H₅₇NO₆Si
Molecular Weight:591.904
Hs Code.:

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

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

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

There total 6 articles about tert-butyl (2S,5R,3Z)-5-[N-(tert-butoxycarbonyl)amino]-2-[3-(tert-butyldimethylsiloxy)-propyl]-6-(4-methoxyphenyl)-3,4-dimethylhex-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: 79.0%

: 1361407-66-0
tert-butyl (E)-3-[(4R,5R)-N-(tert-butoxycarbonyl)-4-(4-methoxybenzyl)-5-methyl-1,3-oxazolidin-2-on-5-yl]but-2-enoate

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

: 1361407-76-2
tert-butyl (2S,5R,3Z)-5-[N-(tert-butoxycarbonyl)amino]-2-[3-(tert-butyldimethylsiloxy)-propyl]-6-(4-methoxyphenyl)-3,4-dimethylhex-3-enoate

: 1361407-68-2
tert-butyl (2R,5R,3E)-5-[N-(tert-butoxycarbonyl)amino]-2-[3-(tert-butyldimethylsiloxy)-propyl]-6-(4-methoxyphenyl)-3,4-dimethylhex-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:

: 1275576-22-1
(R)-N-(tert-butoxycarbonyl)-2-amino-3-(p-methyloxyphenyl)-N-methoxy-N-methylpropionamide

: 1361407-76-2
tert-butyl (2S,5R,3Z)-5-[N-(tert-butoxycarbonyl)amino]-2-[3-(tert-butyldimethylsiloxy)-propyl]-6-(4-methoxyphenyl)-3,4-dimethylhex-3-enoate

: 1361407-68-2
tert-butyl (2R,5R,3E)-5-[N-(tert-butoxycarbonyl)amino]-2-[3-(tert-butyldimethylsiloxy)-propyl]-6-(4-methoxyphenyl)-3,4-dimethylhex-3-enoate

Guidance literature:: Multi-step reaction with 6 steps

1.1: tetrahydrofuran / 1.5 h / -78 °C / Inert atmosphere

2.1: cerium(III) chloride / tetrahydrofuran / 3 h / 0 °C / Inert atmosphere

3.1: sodium hydride / tetrahydrofuran; mineral oil / 1.5 h / 0 °C / Inert atmosphere; Reflux

3.2: 2 h / 0 °C / Inert atmosphere

4.1: dimethylsulfide; ozone / ethyl acetate / 0.25 h / -78 - 0 °C

5.1: toluene / 10 h / Reflux

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

With cerium(III) chloride; dimethylsulfide; copper(l) cyanide; sodium hydride; ozone; lithium chloride; In tetrahydrofuran; diethyl ether; ethyl acetate; toluene; mineral oil; pentane; 5.1: Wittig reaction;
DOI:10.1021/jm2016914

Reference yield:

: 1361407-61-5
(3R,4R)-4-[N-(tert-butoxycarbonyl)amino]-5-(4-methoxyphenyl)-2,3-dimethylpent-1-en-3-ol

: 1361407-76-2
tert-butyl (2S,5R,3Z)-5-[N-(tert-butoxycarbonyl)amino]-2-[3-(tert-butyldimethylsiloxy)-propyl]-6-(4-methoxyphenyl)-3,4-dimethylhex-3-enoate

: 1361407-68-2
tert-butyl (2R,5R,3E)-5-[N-(tert-butoxycarbonyl)amino]-2-[3-(tert-butyldimethylsiloxy)-propyl]-6-(4-methoxyphenyl)-3,4-dimethylhex-3-enoate

Guidance literature:: Multi-step reaction with 4 steps

1.1: sodium hydride / tetrahydrofuran; mineral oil / 1.5 h / 0 °C / Inert atmosphere; Reflux

1.2: 2 h / 0 °C / Inert atmosphere

2.1: dimethylsulfide; ozone / ethyl acetate / 0.25 h / -78 - 0 °C

3.1: toluene / 10 h / Reflux

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

With dimethylsulfide; copper(l) cyanide; sodium hydride; ozone; lithium chloride; In tetrahydrofuran; diethyl ether; ethyl acetate; toluene; mineral oil; pentane; 3.1: Wittig reaction;
DOI:10.1021/jm2016914