2-[(E)-(2S,3R)-2-((S)-4-Benzyl-2-oxo-oxazolidine-3-carbonyl)-6-((S)-2,2-dimethyl-[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

Base Information

Chemical Name:2-[(E)-(2S,3R)-2-((S)-4-Benzyl-2-oxo-oxazolidine-3-carbonyl)-6-((S)-2,2-dimethyl-[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
CAS No.:1027920-60-0
Molecular Formula:C₄₁H₅₇NO₁₀S
Molecular Weight:755.97
Hs Code.:

2-[(E)-(2S,3R)-2-((S)-4-Benzyl-2-oxo-oxazolidine-3-carbonyl)-6-((S)-2,2-dimethyl-[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

Synonyms:2-[(E)-(2S,3R)-2-((S)-4-Benzyl-2-oxo-oxazolidine-3-carbonyl)-6-((S)-2,2-dimethyl-[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

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Chemical Property of 2-[(E)-(2S,3R)-2-((S)-4-Benzyl-2-oxo-oxazolidine-3-carbonyl)-6-((S)-2,2-dimethyl-[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

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Technology Process of 2-[(E)-(2S,3R)-2-((S)-4-Benzyl-2-oxo-oxazolidine-3-carbonyl)-6-((S)-2,2-dimethyl-[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

There total 5 articles about 2-[(E)-(2S,3R)-2-((S)-4-Benzyl-2-oxo-oxazolidine-3-carbonyl)-6-((S)-2,2-dimethyl-[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 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: 71.0%

: 298195-01-4
2-[3-((S)-4-Benzyl-2-oxo-oxazolidin-3-yl)-3-oxo-propyl]-2-{(2E,9E)-1-[1-ethylsulfanyl-meth-(Z)-ylidene]-undeca-2,9-dienyl}-malonic acid dimethyl ester

: (E)-4-((S)-2,2-dimethyl-1,3-dioxolan-4-yl)but-2-enal

: 1027920-60-0
2-[(E)-(2S,3R)-2-((S)-4-Benzyl-2-oxo-oxazolidine-3-carbonyl)-6-((S)-2,2-dimethyl-[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

Guidance literature:: 2-[3-((S)-4-Benzyl-2-oxo-oxazolidin-3-yl)-3-oxo-propyl]-2-{(2E,9E)-1-[1-ethylsulfanyl-meth-(Z)-ylidene]-undeca-2,9-dienyl}-malonic acid dimethyl ester; With di-n-butylboryl trifluoromethanesulfonate; In dichloromethane; at -78 ℃; for 1h;

With triethylamine; In dichloromethane; at -78 - 0 ℃; for 1h;

(E)-4-((S)-2,2-dimethyl-1,3-dioxolan-4-yl)but-2-enal; In dichloromethane; at 0 ℃; for 1h;
DOI:10.1021/ol034471c

Reference yield:

: 32233-44-6
2-[(4S)-2,2-dimethyl-1,3-dioxolan-4-yl]acetaldehyde

: 1027920-60-0
2-[(E)-(2S,3R)-2-((S)-4-Benzyl-2-oxo-oxazolidine-3-carbonyl)-6-((S)-2,2-dimethyl-[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

Guidance literature:: Multi-step reaction with 3 steps

1.1: tetrahydrofuran; diethyl ether / 1 h / 0 °C

2.1: acetic anhydride; 4-(N,N-dimethylamino)pyridine / pyridine / 1 h / 20 °C

2.2: O₃ / CH₂Cl₂; methanol / 2.5 h / -78 °C

2.3: 14 g / dimethyl sulfide; triethylamine / CH₂Cl₂; methanol / 1.5 h / 0 °C

3.1: dibutylboron trifluoromethanesulfonate / CH₂Cl₂ / 1 h / -78 °C

3.2: triethylamine / CH₂Cl₂ / 1 h / -78 - 0 °C

3.3: 71 percent / CH₂Cl₂ / 1 h / 0 °C

With dmap; di-n-butylboryl trifluoromethanesulfonate; acetic anhydride; In tetrahydrofuran; pyridine; diethyl ether; dichloromethane; 3.3: Evans' aldol reaction;
DOI:10.1021/ol034471c

Reference yield:

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

: 1027920-60-0
2-[(E)-(2S,3R)-2-((S)-4-Benzyl-2-oxo-oxazolidine-3-carbonyl)-6-((S)-2,2-dimethyl-[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

Guidance literature:: Multi-step reaction with 2 steps

1.1: 73 percent / Cs₂CO₃ / acetonitrile / 50 °C

2.1: dibutylboron trifluoromethanesulfonate / CH₂Cl₂ / 1 h / -78 °C

2.2: triethylamine / CH₂Cl₂ / 1 h / -78 - 0 °C

2.3: 71 percent / CH₂Cl₂ / 1 h / 0 °C

With di-n-butylboryl trifluoromethanesulfonate; caesium carbonate; In dichloromethane; acetonitrile; 1.1: Michael reaction / 2.3: Evans' aldol reaction;
DOI:10.1021/ol034471c