(1'''E)-5-{3'-p-Bromobenzoyloxy-3'-[furan-2''(5''H)-on-4''-yl]propyl}-5-(buta-1''',3'''-dienyl)-2,2-dimethyl-1,3-dioxane

Base Information

• Chemical Name: (1'''E)-5-{3'-p-Bromobenzoyloxy-3'-[furan-2''(5''H)-on-4''-yl]propyl}-5-(buta-1''',3'''-dienyl)-2,2-dimethyl-1,3-dioxane
• CAS No.: 171201-08-4
• Molecular Formula: C₂₄H₂₇BrO₆
• Molecular Weight: 491.379

Synonyms:

Chemical Property of (1'''E)-5-{3'-p-Bromobenzoyloxy-3'-[furan-2''(5''H)-on-4''-yl]propyl}-5-(buta-1''',3'''-dienyl)-2,2-dimethyl-1,3-dioxane

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (1'''E)-5-{3'-p-Bromobenzoyloxy-3'-[furan-2''(5''H)-on-4''-yl]propyl}-5-(buta-1''',3'''-dienyl)-2,2-dimethyl-1,3-dioxane

There total 16 articles about (1'''E)-5-{3'-p-Bromobenzoyloxy-3'-[furan-2''(5''H)-on-4''-yl]propyl}-5-(buta-1''',3'''-dienyl)-2,2-dimethyl-1,3-dioxane 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:

Ethyl 2-ethoxycarbonyl-4-(1',3'-dioxolan-2'-yl)butanoate (23985-06-0) → (1'''E)-5-{3'-p-Bromobenzoyloxy-3'-[furan-2''(5''H)-on-4''-yl]propyl}-5-(buta-1''',3'''-dienyl)-2,2-dimethyl-1,3-dioxane (171201-08-4)

Guidance literature:

Multi-step reaction with 17 steps

1.1: NaOEt / ethanol / 0.5 h

1.2: 95 percent / ethanol / 0.33 h / 20 °C

2.1: 24.03 g / LAH / diethyl ether / 1.67 h / 20 °C

3.1: 6.18 g / Et₃N; DMAP / CH₂Cl₂ / 0.58 h / 20 °C

4.1: 98 percent / TiCl₄ / CH₂Cl₂ / 0.37 h / 0 °C

5.1: 7.17 g / LAH / diethyl ether / 1.5 h / 0 °C

6.1: 7.22 g / PPTS / CH₂Cl₂ / 4.5 h / 25 °C

7.1: 71 percent / MeI; H₂O; CaCO₃ / acetonitrile / 18 h / 20 - 40 °C

8.1: BuLi / diethyl ether; hexane / 1 h / -78 °C

8.2: 2.11 g / diethyl ether; hexane / 1 h / -78 °C

9.1: 551 mg / TBAF / tetrahydrofuran / 0.25 h / 0 °C

10.1: 76 percent / imidazole / dimethylformamide / 10 h / 25 °C

11.1: 244.5 mg / NMO; OsO₄; H₂O / tetrahydrofuran; 2-methyl-propan-2-ol / 13 h / 25 °C

12.1: 184.6 mg / aq. NaIO₄ / methanol / 0.33 h / 0 °C

13.1: 10.27 g / tetrahydrofuran / 0.23 h / -78 °C

14.1: 70 percent / pyridine / 1.83 h / 0 - 20 °C

15.1: 77 percent / Et₃N / Pd(PPh₃)4 / tetrahydrofuran / 0.67 h / 55 °C

16.1: 98 percent / TBAF / tetrahydrofuran / 0.2 h / 0 °C

17.1: 91 percent

With pyridine; 1H-imidazole; dmap; sodium periodate; osmium(VIII) oxide; lithium aluminium tetrahydride; n-butyllithium; N-methyl-2-indolinone; tetrabutyl ammonium fluoride; water; sodium ethanolate; pyridinium p-toluenesulfonate; titanium tetrachloride; triethylamine; calcium carbonate; methyl iodide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In tetrahydrofuran; methanol; diethyl ether; ethanol; hexane; dichloromethane; N,N-dimethyl-formamide; acetonitrile; tert-butyl alcohol; 1.1: Metallation / 1.2: Alkylation / 2.1: Reduction / 3.1: Acetylation / 4.1: Substitution / 5.1: Reduction / 6.1: Cyclization / 7.1: Methylation / 8.1: Metallation / 8.2: Alkylation / 9.1: Silyl ether cleavage / 10.1: Etherification / 11.1: Addition / 12.1: Oxidation / 13.1: Grignard reaction / 14.1: Acylation / 15.1: Elimination / 16.1: Silyl ether cleavage / 17.1: Esterification;

DOI:10.1055/s-2000-8223

Reference yield:

3-[2',2'-Dimethyl-1',3'-dioxa-5'-(prop-2''-enyl)]propanal (171201-17-5) → (1'''E)-5-{3'-p-Bromobenzoyloxy-3'-[furan-2''(5''H)-on-4''-yl]propyl}-5-(buta-1''',3'''-dienyl)-2,2-dimethyl-1,3-dioxane (171201-08-4)

Guidance literature:

Multi-step reaction with 10 steps

1.1: BuLi / diethyl ether; hexane / 1 h / -78 °C

1.2: 2.11 g / diethyl ether; hexane / 1 h / -78 °C

2.1: 551 mg / TBAF / tetrahydrofuran / 0.25 h / 0 °C

3.1: 76 percent / imidazole / dimethylformamide / 10 h / 25 °C

4.1: 244.5 mg / NMO; OsO₄; H₂O / tetrahydrofuran; 2-methyl-propan-2-ol / 13 h / 25 °C

5.1: 184.6 mg / aq. NaIO₄ / methanol / 0.33 h / 0 °C

6.1: 10.27 g / tetrahydrofuran / 0.23 h / -78 °C

7.1: 70 percent / pyridine / 1.83 h / 0 - 20 °C

8.1: 77 percent / Et₃N / Pd(PPh₃)4 / tetrahydrofuran / 0.67 h / 55 °C

9.1: 98 percent / TBAF / tetrahydrofuran / 0.2 h / 0 °C

10.1: 91 percent

With pyridine; 1H-imidazole; sodium periodate; osmium(VIII) oxide; n-butyllithium; N-methyl-2-indolinone; tetrabutyl ammonium fluoride; water; triethylamine; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In tetrahydrofuran; methanol; diethyl ether; hexane; N,N-dimethyl-formamide; tert-butyl alcohol; 1.1: Metallation / 1.2: Alkylation / 2.1: Silyl ether cleavage / 3.1: Etherification / 4.1: Addition / 5.1: Oxidation / 6.1: Grignard reaction / 7.1: Acylation / 8.1: Elimination / 9.1: Silyl ether cleavage / 10.1: Esterification;

DOI:10.1055/s-2000-8223

Reference yield:

4,4-Dihydroxymethyl-6-(1',3'-dioxolan-2'-yl)hex-1-ene (171201-01-7) → (1'''E)-5-{3'-p-Bromobenzoyloxy-3'-[furan-2''(5''H)-on-4''-yl]propyl}-5-(buta-1''',3'''-dienyl)-2,2-dimethyl-1,3-dioxane (171201-08-4)

Guidance literature:

Multi-step reaction with 15 steps

1.1: 6.18 g / Et₃N; DMAP / CH₂Cl₂ / 0.58 h / 20 °C

2.1: 98 percent / TiCl₄ / CH₂Cl₂ / 0.37 h / 0 °C

3.1: 7.17 g / LAH / diethyl ether / 1.5 h / 0 °C

4.1: 7.22 g / PPTS / CH₂Cl₂ / 4.5 h / 25 °C

5.1: 71 percent / MeI; H₂O; CaCO₃ / acetonitrile / 18 h / 20 - 40 °C

6.1: BuLi / diethyl ether; hexane / 1 h / -78 °C

6.2: 2.11 g / diethyl ether; hexane / 1 h / -78 °C

7.1: 551 mg / TBAF / tetrahydrofuran / 0.25 h / 0 °C

8.1: 76 percent / imidazole / dimethylformamide / 10 h / 25 °C

9.1: 244.5 mg / NMO; OsO₄; H₂O / tetrahydrofuran; 2-methyl-propan-2-ol / 13 h / 25 °C

10.1: 184.6 mg / aq. NaIO₄ / methanol / 0.33 h / 0 °C

11.1: 10.27 g / tetrahydrofuran / 0.23 h / -78 °C

12.1: 70 percent / pyridine / 1.83 h / 0 - 20 °C

13.1: 77 percent / Et₃N / Pd(PPh₃)4 / tetrahydrofuran / 0.67 h / 55 °C

14.1: 98 percent / TBAF / tetrahydrofuran / 0.2 h / 0 °C

15.1: 91 percent

With pyridine; 1H-imidazole; dmap; sodium periodate; osmium(VIII) oxide; lithium aluminium tetrahydride; n-butyllithium; N-methyl-2-indolinone; tetrabutyl ammonium fluoride; water; pyridinium p-toluenesulfonate; titanium tetrachloride; triethylamine; calcium carbonate; methyl iodide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In tetrahydrofuran; methanol; diethyl ether; hexane; dichloromethane; N,N-dimethyl-formamide; acetonitrile; tert-butyl alcohol; 1.1: Acetylation / 2.1: Substitution / 3.1: Reduction / 4.1: Cyclization / 5.1: Methylation / 6.1: Metallation / 6.2: Alkylation / 7.1: Silyl ether cleavage / 8.1: Etherification / 9.1: Addition / 10.1: Oxidation / 11.1: Grignard reaction / 12.1: Acylation / 13.1: Elimination / 14.1: Silyl ether cleavage / 15.1: Esterification;

DOI:10.1055/s-2000-8223

upstream raw materials:

Ethyl 2-ethoxycarbonyl-4-(1',3'-dioxolan-2'-yl)butanoate

3-[2',2'-Dimethyl-1',3'-dioxa-5'-(prop-2''-enyl)]propanal

4,4-Dihydroxymethyl-6-(1',3'-dioxolan-2'-yl)hex-1-ene

4,4-Dihydroxymethyl-6-(1',3'-diothian-2'-yl)hex-1-ene

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