4-{(5aR,6R,7R,8aS)-7-hydroxy-6-[(1E,3R)-3-hydroxy-4-phenoxy-1-buten-1-yl]-5,5a,6,7,8,8a-hexahydro-2H-cyclopenta[b]oxepin-3-yl}butanoic acid

Base Information

Chemical Name:4-{(5aR,6R,7R,8aS)-7-hydroxy-6-[(1E,3R)-3-hydroxy-4-phenoxy-1-buten-1-yl]-5,5a,6,7,8,8a-hexahydro-2H-cyclopenta[b]oxepin-3-yl}butanoic acid
CAS No.:1262874-46-3
Molecular Formula:C₂₃H₃₀O₆
Molecular Weight:402.488
Hs Code.:

Synonyms:4-{(5aR,6R,7R,8aS)-7-hydroxy-6-[(1E,3R)-3-hydroxy-4-phenoxy-1-buten-1-yl]-5,5a,6,7,8,8a-hexahydro-2H-cyclopenta[b]oxepin-3-yl}butanoic acid

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Chemical Property of 4-{(5aR,6R,7R,8aS)-7-hydroxy-6-[(1E,3R)-3-hydroxy-4-phenoxy-1-buten-1-yl]-5,5a,6,7,8,8a-hexahydro-2H-cyclopenta[b]oxepin-3-yl}butanoic acid

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Technology Process of 4-{(5aR,6R,7R,8aS)-7-hydroxy-6-[(1E,3R)-3-hydroxy-4-phenoxy-1-buten-1-yl]-5,5a,6,7,8,8a-hexahydro-2H-cyclopenta[b]oxepin-3-yl}butanoic acid

There total 13 articles about 4-{(5aR,6R,7R,8aS)-7-hydroxy-6-[(1E,3R)-3-hydroxy-4-phenoxy-1-buten-1-yl]-5,5a,6,7,8,8a-hexahydro-2H-cyclopenta[b]oxepin-3-yl}butanoic acid 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%

: e-[(5aR,6R,7R,8aS)-7-hydroxy-6-[(E,3R)-3-hydroxy-4-phenoxy-but-1-enyl]-5,5a,6,7,8,8a-hexahydro-2H-cyclopenta[b]oxepin-3-yl]butanoate

: 1262874-46-3
4-{(5aR,6R,7R,8aS)-7-hydroxy-6-[(1E,3R)-3-hydroxy-4-phenoxy-1-buten-1-yl]-5,5a,6,7,8,8a-hexahydro-2H-cyclopenta[b]oxepin-3-yl}butanoic acid

Guidance literature:: With sodium hydroxide; In methanol; water; at 20 ℃; for 8h;
DOI:10.1021/acsmedchemlett.6b00415

Reference yield:

: 1262872-69-4
{[(1S,2R,3S,5R)-2-allyl-3-[(2-bromo-2-propen-1-yl)oxy]-5-(tetrahydro-2H-pyran-2-yloxy)cyclopentyl]methoxy}(dimethyl)(2-methyl-2-propanyl)silane

: 1262874-46-3
4-{(5aR,6R,7R,8aS)-7-hydroxy-6-[(1E,3R)-3-hydroxy-4-phenoxy-1-buten-1-yl]-5,5a,6,7,8,8a-hexahydro-2H-cyclopenta[b]oxepin-3-yl}butanoic acid

Guidance literature:: Multi-step reaction with 8 steps

1: bis(tri-t-butylphosphine)palladium⁽⁰⁾ / toluene; tetrahydrofuran / 3 h / 80 °C

2: [1,3-bis(2,4,6-trimethylphenyl)-2-imidazolidinylidene]dichloro-(3-phenyl-1H-inden-1-ylidene)(tricyclohexylphosphine)ruthenium(II) / toluene / 3 h / 80 °C

3: tetrabutyl ammonium fluoride / tetrahydrofuran / 3 h / 20 °C

4: pyridine-SO₃ complex; N-ethyl-N,N-diisopropylamine / ethyl acetate / 1 h / 0 °C

5: potassium phosphate / tetrahydrofuran / 20 °C

6: (3aR)-1-methyl-3,3-diphenyl-tetrahydro-pyrrolo[1,2-c][1,3,2]oxazaborole; dimethylsulfide borane complex / tetrahydrofuran; dichloromethane / 1 h / 20 °C

7: acetic acid / tetrahydrofuran; water / 5 h / 60 °C

8: sodium hydroxide / water; methanol / 8 h / 20 °C

With potassium phosphate; bis(tri-t-butylphosphine)palladium⁽⁰⁾; pyridine-SO₃ complex; [1,3-bis(2,4,6-trimethylphenyl)-2-imidazolidinylidene]dichloro-(3-phenyl-1H-inden-1-ylidene)(tricyclohexylphosphine)ruthenium(II); dimethylsulfide borane complex; tetrabutyl ammonium fluoride; acetic acid; N-ethyl-N,N-diisopropylamine; sodium hydroxide; (3aR)-1-methyl-3,3-diphenyl-tetrahydro-pyrrolo[1,2-c][1,3,2]oxazaborole; In tetrahydrofuran; methanol; dichloromethane; water; ethyl acetate; toluene; 1: |Negishi Coupling / 5: |Horner-Wadsworth-Emmons Olefination;
DOI:10.1021/acsmedchemlett.6b00415

Reference yield:

: ethyl 5-[[(1S,2R,3S,4R)-2-allyl-3-[[tert-butyl(dimethyl)silyl]oxymethyl]-4-tetrahydropyran-2-yloxy-cyclopentoxy]methyl]hex-5-enoate

: 1262874-46-3
4-{(5aR,6R,7R,8aS)-7-hydroxy-6-[(1E,3R)-3-hydroxy-4-phenoxy-1-buten-1-yl]-5,5a,6,7,8,8a-hexahydro-2H-cyclopenta[b]oxepin-3-yl}butanoic acid

Guidance literature:: Multi-step reaction with 7 steps

1: [1,3-bis(2,4,6-trimethylphenyl)-2-imidazolidinylidene]dichloro-(3-phenyl-1H-inden-1-ylidene)(tricyclohexylphosphine)ruthenium(II) / toluene / 3 h / 80 °C

2: tetrabutyl ammonium fluoride / tetrahydrofuran / 3 h / 20 °C

3: pyridine-SO₃ complex; N-ethyl-N,N-diisopropylamine / ethyl acetate / 1 h / 0 °C

4: potassium phosphate / tetrahydrofuran / 20 °C

5: (3aR)-1-methyl-3,3-diphenyl-tetrahydro-pyrrolo[1,2-c][1,3,2]oxazaborole; dimethylsulfide borane complex / tetrahydrofuran; dichloromethane / 1 h / 20 °C

6: acetic acid / tetrahydrofuran; water / 5 h / 60 °C

7: sodium hydroxide / water; methanol / 8 h / 20 °C

With potassium phosphate; pyridine-SO₃ complex; [1,3-bis(2,4,6-trimethylphenyl)-2-imidazolidinylidene]dichloro-(3-phenyl-1H-inden-1-ylidene)(tricyclohexylphosphine)ruthenium(II); dimethylsulfide borane complex; tetrabutyl ammonium fluoride; acetic acid; N-ethyl-N,N-diisopropylamine; sodium hydroxide; (3aR)-1-methyl-3,3-diphenyl-tetrahydro-pyrrolo[1,2-c][1,3,2]oxazaborole; In tetrahydrofuran; methanol; dichloromethane; water; ethyl acetate; toluene; 4: |Horner-Wadsworth-Emmons Olefination;
DOI:10.1021/acsmedchemlett.6b00415