(1S,4E,7E,10E,13R,15S)-5-(2-(tert-butyldimethylsilyloxy)ethyl)-11-methyl-15-((E)-3-methyl-5-phenylpent-3-enyl)-2,14-dioxabicyclo[11.3.1]heptadeca-4,7,10-trien-3-one

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Chemical Name:(1S,4E,7E,10E,13R,15S)-5-(2-(tert-butyldimethylsilyloxy)ethyl)-11-methyl-15-((E)-3-methyl-5-phenylpent-3-enyl)-2,14-dioxabicyclo[11.3.1]heptadeca-4,7,10-trien-3-one
CAS No.:1375950-88-1
Molecular Formula:C₃₆H₅₄O₄Si
Molecular Weight:578.908
Hs Code.:

(1S,4E,7E,10E,13R,15S)-5-(2-(tert-butyldimethylsilyloxy)ethyl)-11-methyl-15-((E)-3-methyl-5-phenylpent-3-enyl)-2,14-dioxabicyclo[11.3.1]heptadeca-4,7,10-trien-3-one

Synonyms:(1S,4E,7E,10E,13R,15S)-5-(2-(tert-butyldimethylsilyloxy)ethyl)-11-methyl-15-((E)-3-methyl-5-phenylpent-3-enyl)-2,14-dioxabicyclo[11.3.1]heptadeca-4,7,10-trien-3-one

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Chemical Property of (1S,4E,7E,10E,13R,15S)-5-(2-(tert-butyldimethylsilyloxy)ethyl)-11-methyl-15-((E)-3-methyl-5-phenylpent-3-enyl)-2,14-dioxabicyclo[11.3.1]heptadeca-4,7,10-trien-3-one

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Technology Process of (1S,4E,7E,10E,13R,15S)-5-(2-(tert-butyldimethylsilyloxy)ethyl)-11-methyl-15-((E)-3-methyl-5-phenylpent-3-enyl)-2,14-dioxabicyclo[11.3.1]heptadeca-4,7,10-trien-3-one

There total 21 articles about (1S,4E,7E,10E,13R,15S)-5-(2-(tert-butyldimethylsilyloxy)ethyl)-11-methyl-15-((E)-3-methyl-5-phenylpent-3-enyl)-2,14-dioxabicyclo[11.3.1]heptadeca-4,7,10-trien-3-one 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: 84.0%

: 1375951-01-1
(2S,4S,6R)-2-((E)-3-methyl-5-phenylpent-3-en-1-yl)-6-((E)-2-methylhexa-2,5-dien-1-yl)tetrahydro-2H-pyran-4-yl-(E)-3-(2-((tert-butyldimethylsilyl)oxy)ethyl)hexa-2,5-dienoate

: 1375950-88-1
(1S,4E,7E,10E,13R,15S)-5-(2-(tert-butyldimethylsilyloxy)ethyl)-11-methyl-15-((E)-3-methyl-5-phenylpent-3-enyl)-2,14-dioxabicyclo[11.3.1]heptadeca-4,7,10-trien-3-one

Guidance literature:: With tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; In dichloromethane; at 20 ℃; for 48h;
DOI:10.1002/anie.201108749

Reference yield: 84.0%

: (2S,4S,6R)-2-((E)-3-methyl-5-phenylpent-3-en-1-yl)-6-((E)-2-methylhexa-2,5-dien-1-yl)tetrahydro-2H-pyran-4-yl-(E)-5-((tert-butyldimethylsilyl)oxy)-3-methylpent-2-enoate

: 1375950-88-1
(1S,4E,7E,10E,13R,15S)-5-(2-(tert-butyldimethylsilyloxy)ethyl)-11-methyl-15-((E)-3-methyl-5-phenylpent-3-enyl)-2,14-dioxabicyclo[11.3.1]heptadeca-4,7,10-trien-3-one

Guidance literature:: (2S,4S,6R)-2-((E)-3-methyl-5-phenylpent-3-en-1-yl)-6-((E)-2-methylhexa-2,5-dien-1-yl)tetrahydro-2H-pyran-4-yl-(E)-5-((tert-butyldimethylsilyl)oxy)-3-methylpent-2-enoate; With tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; In dichloromethane; at 20 ℃; for 48h; Inert atmosphere;

With dimethyl sulfoxide; In dichloromethane; for 1h; Inert atmosphere;
DOI:10.1002/chem.201403176

Reference yield:

: 1375950-84-7
(3-((2R,4R,6S)-6-(but-3-ynyl)-4-(tert-butyldimethylsilyloxy)tetrahydro-2H-pyran-2-yl)prop-1-ynyl)trimethylsilane

: 1375950-88-1
(1S,4E,7E,10E,13R,15S)-5-(2-(tert-butyldimethylsilyloxy)ethyl)-11-methyl-15-((E)-3-methyl-5-phenylpent-3-enyl)-2,14-dioxabicyclo[11.3.1]heptadeca-4,7,10-trien-3-one

Guidance literature:: Multi-step reaction with 8 steps

1.1: zirconocene dichloride; tert-butyl alcohol / dichloromethane; toluene / 24 h / 0 - 20 °C / Inert atmosphere

1.2: 5 h / 0 °C / Inert atmosphere

2.1: tetrakis(triphenylphosphine) palladium⁽⁰⁾ / tetrahydrofuran; 1-methyl-pyrrolidin-2-one / 60 h / 20 °C / Inert atmosphere

3.1: potassium carbonate / tetrahydrofuran; methanol / 3 h / 0 - 20 °C

4.1: zirconocene dichloride; tert-butyl alcohol / dichloromethane; toluene / 0 - 20 °C / Inert atmosphere

4.2: -20 - 20 °C / Inert atmosphere

5.1: camphor-10-sulfonic acid / tetrahydrofuran; methanol / 2 h / 20 °C

6.1: di-isopropyl azodicarboxylate; triphenylphosphine / benzene / 1.5 h / 20 °C

7.1: tetrakis(triphenylphosphine) palladium⁽⁰⁾ / N,N-dimethyl-formamide; benzene / 1.5 h / 60 °C

8.1: tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride / dichloromethane / 48 h / 20 °C

With tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; tetrakis(triphenylphosphine) palladium⁽⁰⁾; zirconocene dichloride; di-isopropyl azodicarboxylate; camphor-10-sulfonic acid; potassium carbonate; triphenylphosphine; tert-butyl alcohol; In tetrahydrofuran; 1-methyl-pyrrolidin-2-one; methanol; dichloromethane; N,N-dimethyl-formamide; toluene; benzene; 2.1: Negishi coupling reaction / 6.1: Mitsunobu reaction / 7.1: Stille cross-coupling;
DOI:10.1002/anie.201108749