(4R)-Z-3-(3,4-methylenedioxyphenyl)-4,5-(N-triphenylmethylepimino)-2-pentenoic acid ethyl ester

Base Information

Chemical Name:(4R)-Z-3-(3,4-methylenedioxyphenyl)-4,5-(N-triphenylmethylepimino)-2-pentenoic acid ethyl ester
CAS No.:236742-92-0
Molecular Formula:C₃₃H₂₉NO₄
Molecular Weight:503.598
Hs Code.:

Synonyms:(4R)-Z-3-(3,4-methylenedioxyphenyl)-4,5-(N-triphenylmethylepimino)-2-pentenoic acid ethyl ester

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Chemical Property of (4R)-Z-3-(3,4-methylenedioxyphenyl)-4,5-(N-triphenylmethylepimino)-2-pentenoic acid ethyl ester

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Technology Process of (4R)-Z-3-(3,4-methylenedioxyphenyl)-4,5-(N-triphenylmethylepimino)-2-pentenoic acid ethyl ester

There total 4 articles about (4R)-Z-3-(3,4-methylenedioxyphenyl)-4,5-(N-triphenylmethylepimino)-2-pentenoic acid ethyl ester 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: 41.0%

: 867-13-0
diethoxyphosphoryl-acetic acid ethyl ester

: 3,4-methylenedioxyphenyl (1S)-N-triphenylmethylaziridinyl ketone

: 236742-92-0
(4R)-Z-3-(3,4-methylenedioxyphenyl)-4,5-(N-triphenylmethylepimino)-2-pentenoic acid ethyl ester

: 236742-93-1
(4R)-E-3-(3,4-methylenedioxyphenyl)-4,5-(N-triphenylmethylepimino)-2-pentenoic acid ethyl ester

Guidance literature:: diethoxyphosphoryl-acetic acid ethyl ester; With sodium hydride; In tetrahydrofuran; at 0 - 20 ℃; for 2h;

3,4-methylenedioxyphenyl (1S)-N-triphenylmethylaziridinyl ketone; In tetrahydrofuran; at 20 ℃; for 48h;
DOI:10.1016/S0040-4020(99)00345-2

Reference yield:

: 152706-54-2
1-triphenylmethyl-2-aziridinecarboxaldehyde

: 236742-92-0
(4R)-Z-3-(3,4-methylenedioxyphenyl)-4,5-(N-triphenylmethylepimino)-2-pentenoic acid ethyl ester

Guidance literature:: Multi-step reaction with 3 steps

1.1: nBuLi / tetrahydrofuran; hexane / 1.5 h / -78 °C

1.2: 64 percent / tetrahydrofuran; hexane / -78 - 20 °C

2.1: oxalyl chloride; DMSO; Et₃N / CH₂Cl₂ / 3.8 h / -65 - 20 °C

3.1: NaH / tetrahydrofuran / 2 h / 0 - 20 °C

3.2: 17 percent / tetrahydrofuran / 48 h / 20 °C

With n-butyllithium; oxalyl dichloride; sodium hydride; dimethyl sulfoxide; triethylamine; In tetrahydrofuran; hexane; dichloromethane; 1.1: Metallation / 1.2: Grignard reaction / 2.1: Swern oxidation / 3.1: Metallation / 3.2: Horner-Wadsworth-Emmons olefination;
DOI:10.1016/S0040-4020(99)00345-2

Reference yield:

: 152706-23-5
(S)-N-triphenylmethyl-aziridinylmethanol

: 236742-92-0
(4R)-Z-3-(3,4-methylenedioxyphenyl)-4,5-(N-triphenylmethylepimino)-2-pentenoic acid ethyl ester

Guidance literature:: Multi-step reaction with 4 steps

1.1: oxalyl chloride; DMSO; Et₃N / CH₂Cl₂ / 3.8 h / -65 - 20 °C

2.1: nBuLi / tetrahydrofuran; hexane / 1.5 h / -78 °C

2.2: 64 percent / tetrahydrofuran; hexane / -78 - 20 °C

3.1: oxalyl chloride; DMSO; Et₃N / CH₂Cl₂ / 3.8 h / -65 - 20 °C

4.1: NaH / tetrahydrofuran / 2 h / 0 - 20 °C

4.2: 17 percent / tetrahydrofuran / 48 h / 20 °C

With n-butyllithium; oxalyl dichloride; sodium hydride; dimethyl sulfoxide; triethylamine; In tetrahydrofuran; hexane; dichloromethane; 1.1: Swern oxidation / 2.1: Metallation / 2.2: Grignard reaction / 3.1: Swern oxidation / 4.1: Metallation / 4.2: Horner-Wadsworth-Emmons olefination;
DOI:10.1016/S0040-4020(99)00345-2