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

Base Information

Chemical Name:(5R,3Z)-ethyl 5-[(tert-butyldimethylsilyl)oxy]-4-chloro-2-isobutyl-5-phenylpent-3-enoate
CAS No.:1394236-79-3
Molecular Formula:C₂₃H₃₇ClO₃Si
Molecular Weight:425.083
Hs Code.:

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

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

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

There total 4 articles about (5R,3Z)-ethyl 5-[(tert-butyldimethylsilyl)oxy]-4-chloro-2-isobutyl-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: 95.0%

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

: 1394236-79-3
(5R,3Z)-ethyl 5-[(tert-butyldimethylsilyl)oxy]-4-chloro-2-isobutyl-5-phenylpent-3-enoate

: 1394236-83-9
(5R,3Z)-ethyl 5-[(tert-butyldimethylsilyl)oxy]-4-chloro-2-isobutyl-5-phenylpent-3-enoate

Guidance literature:: With 2-methylpropylmagnesium chloride; copper(l) cyanide; In tetrahydrofuran; diethyl ether; at -78 - 20 ℃; for 1.16667h; diastereoselective reaction; Inert atmosphere;
DOI:10.1021/ol301988d

Reference yield:

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

: 1394236-79-3
(5R,3Z)-ethyl 5-[(tert-butyldimethylsilyl)oxy]-4-chloro-2-isobutyl-5-phenylpent-3-enoate

: 1394236-83-9
(5R,3Z)-ethyl 5-[(tert-butyldimethylsilyl)oxy]-4-chloro-2-isobutyl-5-phenylpent-3-enoate

Guidance literature:: Multi-step reaction with 4 steps

1: 2,6-dimethylpyridine / dichloromethane / 12 h / 0 - 20 °C / Inert atmosphere

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

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

4: copper(l) cyanide; 2-methylpropylmagnesium chloride / tetrahydrofuran; diethyl ether / 1.17 h / -78 - 20 °C / Inert atmosphere

With 2,6-dimethylpyridine; 2-methylpropylmagnesium chloride; copper(l) cyanide; diisobutylaluminium hydride; N-ethyl-N,N-diisopropylamine; lithium chloride; In tetrahydrofuran; diethyl ether; dichloromethane; toluene; acetonitrile; 3: |Horner-Wadsworth-Emmons Olefination;
DOI:10.1021/ol301988d

Reference yield:

: 100-52-7
benzaldehyde

: 1394236-79-3
(5R,3Z)-ethyl 5-[(tert-butyldimethylsilyl)oxy]-4-chloro-2-isobutyl-5-phenylpent-3-enoate

: 1394236-83-9
(5R,3Z)-ethyl 5-[(tert-butyldimethylsilyl)oxy]-4-chloro-2-isobutyl-5-phenylpent-3-enoate

Guidance literature:: Multi-step reaction with 5 steps

1: (S)-4-Isopropyl-3-tosyl-[1,3,2]oxazaborolidin-5-one / dichloromethane / -78 °C / Inert atmosphere

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

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

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

5: copper(l) cyanide; 2-methylpropylmagnesium chloride / tetrahydrofuran; diethyl ether / 1.17 h / -78 - 20 °C / Inert atmosphere

With 2,6-dimethylpyridine; 2-methylpropylmagnesium chloride; copper(l) cyanide; diisobutylaluminium hydride; N-ethyl-N,N-diisopropylamine; lithium chloride; (S)-4-Isopropyl-3-tosyl-[1,3,2]oxazaborolidin-5-one; In tetrahydrofuran; diethyl ether; dichloromethane; toluene; acetonitrile; 1: |Mukaiyama Aldol Addition / 4: |Horner-Wadsworth-Emmons Olefination;
DOI:10.1021/ol301988d