2-{(E)-(S)-2-((S)-4-Benzyl-2-oxo-oxazolidine-3-carbonyl)-6-[(4S,5S)-2,2-dimethyl-5-((E)-pent-3-enyl)-[1,3]dioxolan-4-yl]-3-oxo-hex-4-enyl}-2-{(2E,9E)-1-[1-ethylsulfanyl-meth-(Z)-ylidene]-undeca-2,9-dienyl}-malonic acid dimethyl ester

Base Information

Chemical Name:2-{(E)-(S)-2-((S)-4-Benzyl-2-oxo-oxazolidine-3-carbonyl)-6-[(4S,5S)-2,2-dimethyl-5-((E)-pent-3-enyl)-[1,3]dioxolan-4-yl]-3-oxo-hex-4-enyl}-2-{(2E,9E)-1-[1-ethylsulfanyl-meth-(Z)-ylidene]-undeca-2,9-dienyl}-malonic acid dimethyl ester
CAS No.:298195-03-6
Molecular Formula:C₄₆H₆₃NO₁₀S
Molecular Weight:822.073
Hs Code.:

2-{(E)-(S)-2-((S)-4-Benzyl-2-oxo-oxazolidine-3-carbonyl)-6-[(4S,5S)-2,2-dimethyl-5-((E)-pent-3-enyl)-[1,3]dioxolan-4-yl]-3-oxo-hex-4-enyl}-2-{(2E,9E)-1-[1-ethylsulfanyl-meth-(Z)-ylidene]-undeca-2,9-dienyl}-malonic acid dimethyl ester

Synonyms:2-{(E)-(S)-2-((S)-4-Benzyl-2-oxo-oxazolidine-3-carbonyl)-6-[(4S,5S)-2,2-dimethyl-5-((E)-pent-3-enyl)-[1,3]dioxolan-4-yl]-3-oxo-hex-4-enyl}-2-{(2E,9E)-1-[1-ethylsulfanyl-meth-(Z)-ylidene]-undeca-2,9-dienyl}-malonic acid dimethyl ester

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Chemical Property of 2-{(E)-(S)-2-((S)-4-Benzyl-2-oxo-oxazolidine-3-carbonyl)-6-[(4S,5S)-2,2-dimethyl-5-((E)-pent-3-enyl)-[1,3]dioxolan-4-yl]-3-oxo-hex-4-enyl}-2-{(2E,9E)-1-[1-ethylsulfanyl-meth-(Z)-ylidene]-undeca-2,9-dienyl}-malonic acid dimethyl ester

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Technology Process of 2-{(E)-(S)-2-((S)-4-Benzyl-2-oxo-oxazolidine-3-carbonyl)-6-[(4S,5S)-2,2-dimethyl-5-((E)-pent-3-enyl)-[1,3]dioxolan-4-yl]-3-oxo-hex-4-enyl}-2-{(2E,9E)-1-[1-ethylsulfanyl-meth-(Z)-ylidene]-undeca-2,9-dienyl}-malonic acid dimethyl ester

There total 7 articles about 2-{(E)-(S)-2-((S)-4-Benzyl-2-oxo-oxazolidine-3-carbonyl)-6-[(4S,5S)-2,2-dimethyl-5-((E)-pent-3-enyl)-[1,3]dioxolan-4-yl]-3-oxo-hex-4-enyl}-2-{(2E,9E)-1-[1-ethylsulfanyl-meth-(Z)-ylidene]-undeca-2,9-dienyl}-malonic acid dimethyl 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: 75.0%

: 2-{(E)-(S)-2-((S)-4-Benzyl-2-oxo-oxazolidine-3-carbonyl)-6-[(4S,5S)-2,2-dimethyl-5-((E)-pent-3-enyl)-[1,3]dioxolan-4-yl]-3-hydroxy-hex-4-enyl}-2-{(2E,9E)-1-[1-ethylsulfanyl-meth-(Z)-ylidene]-undeca-2,9-dienyl}-malonic acid dimethyl ester

: 298195-03-6
2-{(E)-(S)-2-((S)-4-Benzyl-2-oxo-oxazolidine-3-carbonyl)-6-[(4S,5S)-2,2-dimethyl-5-((E)-pent-3-enyl)-[1,3]dioxolan-4-yl]-3-oxo-hex-4-enyl}-2-{(2E,9E)-1-[1-ethylsulfanyl-meth-(Z)-ylidene]-undeca-2,9-dienyl}-malonic acid dimethyl ester

Guidance literature:: With pyridine-SO₃ complex; N-ethyl-N,N-diisopropylamine; In dimethyl sulfoxide; for 1h;
DOI:10.1021/ja001664b

Reference yield:

: 90719-27-0
(S)-3-acryloyl-4-benzyloxazolidin-2-one

: 298195-03-6
2-{(E)-(S)-2-((S)-4-Benzyl-2-oxo-oxazolidine-3-carbonyl)-6-[(4S,5S)-2,2-dimethyl-5-((E)-pent-3-enyl)-[1,3]dioxolan-4-yl]-3-oxo-hex-4-enyl}-2-{(2E,9E)-1-[1-ethylsulfanyl-meth-(Z)-ylidene]-undeca-2,9-dienyl}-malonic acid dimethyl ester

Guidance literature:: Multi-step reaction with 3 steps

1: 82 percent / Cs₂CO₃ / acetonitrile / 50 °C

2: 80 percent / Bu₂BOTf; Et₃N / CH₂Cl₂ / 1 h / 0 °C

3: 75 percent / SO₃*Py; i-Pr₂NEt / dimethylsulfoxide / 1 h

With pyridine-SO₃ complex; di-n-butylboryl trifluoromethanesulfonate; caesium carbonate; triethylamine; N-ethyl-N,N-diisopropylamine; In dichloromethane; dimethyl sulfoxide; acetonitrile; 1: Michael addition / 3: Parikh-Doering oxidation;
DOI:10.1021/ja001664b

Reference yield:

: 4-Ethylsulfanyl-but-2-ynoic acid methyl ester

: 298195-03-6
2-{(E)-(S)-2-((S)-4-Benzyl-2-oxo-oxazolidine-3-carbonyl)-6-[(4S,5S)-2,2-dimethyl-5-((E)-pent-3-enyl)-[1,3]dioxolan-4-yl]-3-oxo-hex-4-enyl}-2-{(2E,9E)-1-[1-ethylsulfanyl-meth-(Z)-ylidene]-undeca-2,9-dienyl}-malonic acid dimethyl ester

Guidance literature:: Multi-step reaction with 5 steps

1.1: DBU / tetrahydrofuran / 0 °C

1.2: 80 percent / TMSCl; HMPA; Me₂S*THF / -78 - 20 °C

2.1: 84 percent / LHMDS / tetrahydrofuran / -78 °C

3.1: 82 percent / Cs₂CO₃ / acetonitrile / 50 °C

4.1: 80 percent / Bu₂BOTf; Et₃N / CH₂Cl₂ / 1 h / 0 °C

5.1: 75 percent / SO₃*Py; i-Pr₂NEt / dimethylsulfoxide / 1 h

With pyridine-SO₃ complex; di-n-butylboryl trifluoromethanesulfonate; caesium carbonate; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; N-ethyl-N,N-diisopropylamine; lithium hexamethyldisilazane; In tetrahydrofuran; dichloromethane; dimethyl sulfoxide; acetonitrile; 3.1: Michael addition / 5.1: Parikh-Doering oxidation;
DOI:10.1021/ja001664b