3-[(2S,5aR,6R,7R,8aS)-7-hydroxy-6-[(E,3R)-3-hydroxy-4-phenoxy-but-1-enyl]-3,4,5,5a,6,7,8,8a-octahydro-2H-cyclopenta[b]oxepin-2-yl]propanoic acid

Base Information

• Chemical Name: 3-[(2S,5aR,6R,7R,8aS)-7-hydroxy-6-[(E,3R)-3-hydroxy-4-phenoxy-but-1-enyl]-3,4,5,5a,6,7,8,8a-octahydro-2H-cyclopenta[b]oxepin-2-yl]propanoic acid
• CAS No.: 1262874-81-6
• Molecular Formula: C₂₂H₃₀O₆
• Molecular Weight: 390.477

Synonyms:3-[(2S,5aR,6R,7R,8aS)-7-hydroxy-6-[(E,3R)-3-hydroxy-4-phenoxy-but-1-enyl]-3,4,5,5a,6,7,8,8a-octahydro-2H-cyclopenta[b]oxepin-2-yl]propanoic acid

Chemical Property of 3-[(2S,5aR,6R,7R,8aS)-7-hydroxy-6-[(E,3R)-3-hydroxy-4-phenoxy-but-1-enyl]-3,4,5,5a,6,7,8,8a-octahydro-2H-cyclopenta[b]oxepin-2-yl]propanoic acid

Chemical Property:

Purity/Quality:

Safty Information:

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Technology Process of 3-[(2S,5aR,6R,7R,8aS)-7-hydroxy-6-[(E,3R)-3-hydroxy-4-phenoxy-but-1-enyl]-3,4,5,5a,6,7,8,8a-octahydro-2H-cyclopenta[b]oxepin-2-yl]propanoic acid

There total 20 articles about 3-[(2S,5aR,6R,7R,8aS)-7-hydroxy-6-[(E,3R)-3-hydroxy-4-phenoxy-but-1-enyl]-3,4,5,5a,6,7,8,8a-octahydro-2H-cyclopenta[b]oxepin-2-yl]propanoic 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: 100.0%

isopropyl 3-[(2S,5aR,6R,7R,8aS)-7-hydroxy-6-[(E,3R)-3-hydroxy-4-phenoxy-but-1-enyl]-3,4,5,5a,6,7,8,8a-octahydro-2H-cyclopenta[b]oxepin-2-yl]propanoate (1262874-75-8) → 3-[(2S,5aR,6R,7R,8aS)-7-hydroxy-6-[(E,3R)-3-hydroxy-4-phenoxy-but-1-enyl]-3,4,5,5a,6,7,8,8a-octahydro-2H-cyclopenta[b]oxepin-2-yl]propanoic acid (1262874-81-6)

Guidance literature:

With sodium hydroxide; In methanol; water; at 20 ℃; for 8h;

DOI:10.1021/acsmedchemlett.6b00415

Reference yield:

(1S,2R,3S,4R)-3-({[dimethyl(2-methyl-2-propanyl)silyl]oxy}methyl)-2-(1-propen-1-yl)-4-(tetrahydro-2H-pyran-2-yloxy)cyclopentanol (1262874-63-4) → 3-[(2S,5aR,6R,7R,8aS)-7-hydroxy-6-[(E,3R)-3-hydroxy-4-phenoxy-but-1-enyl]-3,4,5,5a,6,7,8,8a-octahydro-2H-cyclopenta[b]oxepin-2-yl]propanoic acid (1262874-81-6)

Guidance literature:

Multi-step reaction with 15 steps

1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 0 - 20 °C

2: sodium hydroxide / tetrahydrofuran; methanol; dihydrogen peroxide / 2 h / 20 °C

3: potassium carbonate / N,N-dimethyl-formamide / 20 °C

4: lithium diisopropyl amide; chloro-trimethyl-silane / tetrahydrofuran; hexane / 1.5 h / -78 - 20 °C

5: ethyl acetate; methanol / 1 h / 20 °C

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

7: lithium aluminium tetrahydride / tetrahydrofuran / 0.25 h / 0 °C

8: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / dimethyl sulfoxide / 5 h

9: sodium hydrogencarbonate; hydrogen; palladium 10% on activated carbon / isopropyl alcohol / 1 h / 20 °C / 760.05 Torr

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

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

12: potassium phosphate / tetrahydrofuran / 20 °C

13: (3aR)-1-methyl-3,3-diphenyl-tetrahydro-pyrrolo[1,2-c][1,3,2]oxazaborole; dimethylsulfide borane complex / tetrahydrofuran; dichloromethane / 1 h / 20 °C

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

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

With potassium phosphate; lithium aluminium tetrahydride; chloro-trimethyl-silane; 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; palladium 10% on activated carbon; tetrabutyl ammonium fluoride; hydrogen; sodium hydride; sodium hydrogencarbonate; potassium carbonate; acetic acid; N-ethyl-N,N-diisopropylamine; sodium hydroxide; (3aR)-1-methyl-3,3-diphenyl-tetrahydro-pyrrolo[1,2-c][1,3,2]oxazaborole; lithium diisopropyl amide; 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione; In tetrahydrofuran; methanol; hexane; dichloromethane; water; dihydrogen peroxide; dimethyl sulfoxide; ethyl acetate; N,N-dimethyl-formamide; isopropyl alcohol; toluene; mineral oil; 4: |Claisen-Ireland Rearrangement / 12: |Horner-Wadsworth-Emmons Olefination;

DOI:10.1021/acsmedchemlett.6b00415

Reference yield:

allyl {[(1S,2R,3S,4R)-3-({[dimethyl(2-methyl-2-propanyl)silyl]oxy}methyl)-2-(1-propen-1-yl)-4-(tetrahydro-2H-pyran-2-yloxy)cyclopentyl]oxy}acetate (1262874-65-6) → 3-[(2S,5aR,6R,7R,8aS)-7-hydroxy-6-[(E,3R)-3-hydroxy-4-phenoxy-but-1-enyl]-3,4,5,5a,6,7,8,8a-octahydro-2H-cyclopenta[b]oxepin-2-yl]propanoic acid (1262874-81-6)

Guidance literature:

Multi-step reaction with 12 steps

1: lithium diisopropyl amide; chloro-trimethyl-silane / tetrahydrofuran; hexane / 1.5 h / -78 - 20 °C

2: ethyl acetate; methanol / 1 h / 20 °C

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

4: lithium aluminium tetrahydride / tetrahydrofuran / 0.25 h / 0 °C

5: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / dimethyl sulfoxide / 5 h

6: sodium hydrogencarbonate; hydrogen; palladium 10% on activated carbon / isopropyl alcohol / 1 h / 20 °C / 760.05 Torr

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

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

9: potassium phosphate / tetrahydrofuran / 20 °C

10: (3aR)-1-methyl-3,3-diphenyl-tetrahydro-pyrrolo[1,2-c][1,3,2]oxazaborole; dimethylsulfide borane complex / tetrahydrofuran; dichloromethane / 1 h / 20 °C

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

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

With potassium phosphate; lithium aluminium tetrahydride; chloro-trimethyl-silane; 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; palladium 10% on activated carbon; tetrabutyl ammonium fluoride; hydrogen; sodium hydrogencarbonate; acetic acid; N-ethyl-N,N-diisopropylamine; sodium hydroxide; (3aR)-1-methyl-3,3-diphenyl-tetrahydro-pyrrolo[1,2-c][1,3,2]oxazaborole; lithium diisopropyl amide; 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione; In tetrahydrofuran; methanol; hexane; dichloromethane; water; dimethyl sulfoxide; ethyl acetate; isopropyl alcohol; toluene; 1: |Claisen-Ireland Rearrangement / 9: |Horner-Wadsworth-Emmons Olefination;

DOI:10.1021/acsmedchemlett.6b00415

upstream raw materials:

(1S,2R,3S,4R)-3-({[dimethyl(2-methyl-2-propanyl)silyl]oxy}methyl)-2-(1-propen-1-yl)-4-(tetrahydro-2H-pyran-2-yloxy)cyclopentanol

2-methyl-2-propanyl {[(1S,2R,3S,4R)-3-({[dimethyl(2-methyl-2-propanyl)silyl]oxy}methyl)-2-(1-propen-1-yl)-4-(tetrahydro-2H-pyran-2-yloxy)cyclopentyl]oxy}acetate

allyl {[(1S,2R,3S,4R)-3-({[dimethyl(2-methyl-2-propanyl)silyl]oxy}methyl)-2-(1-propen-1-yl)-4-(tetrahydro-2H-pyran-2-yloxy)cyclopentyl]oxy}acetate

C₂₂H₄₀O₆Si

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