(5R,3Z)-ethyl 5-[(tert-butyldimethylsilyl)oxy]-4-chloro-2-methyl-5-phenylpent-3-enoate

Base Information

Chemical Name:(5R,3Z)-ethyl 5-[(tert-butyldimethylsilyl)oxy]-4-chloro-2-methyl-5-phenylpent-3-enoate
CAS No.:1394236-76-0
Molecular Formula:C₂₀H₃₁ClO₃Si
Molecular Weight:383.003
Hs Code.:

Synonyms:(5R,3Z)-ethyl 5-[(tert-butyldimethylsilyl)oxy]-4-chloro-2-methyl-5-phenylpent-3-enoate

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Chemical Property of (5R,3Z)-ethyl 5-[(tert-butyldimethylsilyl)oxy]-4-chloro-2-methyl-5-phenylpent-3-enoate

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Technology Process of (5R,3Z)-ethyl 5-[(tert-butyldimethylsilyl)oxy]-4-chloro-2-methyl-5-phenylpent-3-enoate

There total 11 articles about (5R,3Z)-ethyl 5-[(tert-butyldimethylsilyl)oxy]-4-chloro-2-methyl-5-phenylpent-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: 98.0%

: (5R,2Z)-ethyl 5-[(tert-butyldimethylsilyl)oxy]-4,4-dichloro-5-phenylpent-2-enoate

: 1394236-76-0
(5R,3Z)-ethyl 5-[(tert-butyldimethylsilyl)oxy]-4-chloro-2-methyl-5-phenylpent-3-enoate

: 1394236-80-6
(5R,3Z)-ethyl 5-[(tert-butyldimethylsilyl)oxy]-4-chloro-2-methyl-5-phenylpent-3-enoate

Guidance literature:: With methyllithium lithium bromide; copper(l) cyanide; lithium chloride; In tetrahydrofuran; diethyl ether; at -78 - 20 ℃; for 1.16667h; diastereoselective reaction; Inert atmosphere;
DOI:10.1021/ol301988d

Reference yield:

: 1394236-70-4
(2S,5R,3Z)-5-(tert-butyldimethylsilyl)oxy-4-chloro-2-methyl-5-phenylpent-3-enoyl-(S)-sultam

: 1394236-76-0
(5R,3Z)-ethyl 5-[(tert-butyldimethylsilyl)oxy]-4-chloro-2-methyl-5-phenylpent-3-enoate

Guidance literature:: Multi-step reaction with 2 steps

1.1: lithium hydroxide; dihydrogen peroxide / tetrahydrofuran; water / 2 h / 0 - 20 °C

2.1: potassium hydrogencarbonate / N,N-dimethyl-formamide / 0.17 h / 0 °C

2.2: 1 h / 0 - 20 °C

With dihydrogen peroxide; potassium hydrogencarbonate; lithium hydroxide; In tetrahydrofuran; water; N,N-dimethyl-formamide;
DOI:10.1021/ol301988d

Reference yield:

: (3R)-methyl 2,2-dichloro-3-hydroxy-3-phenylpropionate

: 1394236-76-0
(5R,3Z)-ethyl 5-[(tert-butyldimethylsilyl)oxy]-4-chloro-2-methyl-5-phenylpent-3-enoate

Guidance literature:: Multi-step reaction with 6 steps

1.1: 2,6-dimethylpyridine / dichloromethane / 12 h / 0 - 20 °C / Inert atmosphere

2.1: diisobutylaluminium hydride / dichloromethane; toluene / 2 h / -78 °C / Inert atmosphere

3.1: lithium chloride; N-ethyl-N,N-diisopropylamine / acetonitrile / 12.5 h / 0 - 20 °C / Inert atmosphere

4.1: methyllithium lithium bromide; copper(l) iodide / tetrahydrofuran; diethyl ether / 0.67 h / -78 - 0 °C / Inert atmosphere

4.2: 1 h / -78 - -40 °C / Inert atmosphere

4.3: 20.5 h / -40 - 20 °C / Inert atmosphere

5.1: lithium hydroxide; dihydrogen peroxide / tetrahydrofuran; water / 2 h / 0 - 20 °C

6.1: potassium hydrogencarbonate / N,N-dimethyl-formamide / 0.17 h / 0 °C

6.2: 1 h / 0 - 20 °C

With 2,6-dimethylpyridine; copper(l) iodide; methyllithium lithium bromide; dihydrogen peroxide; diisobutylaluminium hydride; potassium hydrogencarbonate; N-ethyl-N,N-diisopropylamine; lithium chloride; lithium hydroxide; In tetrahydrofuran; diethyl ether; dichloromethane; water; N,N-dimethyl-formamide; toluene; acetonitrile; 3.1: |Horner-Wadsworth-Emmons Olefination;
DOI:10.1021/ol301988d