(3aR,4R,5R,6aS)-4-((E)-3-Hydroxy-oct-1-enyl)-hexahydro-cyclopenta[b]furan-2,5-diol

Base Information

• Chemical Name: (3aR,4R,5R,6aS)-4-((E)-3-Hydroxy-oct-1-enyl)-hexahydro-cyclopenta[b]furan-2,5-diol
• CAS No.: 136235-23-9
• Molecular Formula: C₁₅H₂₆O₄
• Molecular Weight: 270.369
• Mol file: 136235-23-9.mol

Synonyms:

Chemical Property of (3aR,4R,5R,6aS)-4-((E)-3-Hydroxy-oct-1-enyl)-hexahydro-cyclopenta[b]furan-2,5-diol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (3aR,4R,5R,6aS)-4-((E)-3-Hydroxy-oct-1-enyl)-hexahydro-cyclopenta[b]furan-2,5-diol

There total 64 articles about (3aR,4R,5R,6aS)-4-((E)-3-Hydroxy-oct-1-enyl)-hexahydro-cyclopenta[b]furan-2,5-diol 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%

7-endo-hydroxy-6-exo-(3'-hydroxyoct-1'-enyl)-3-methoxy-2-oxabicyclo<3.3.0>octane (26114-74-9,50409-26-2,54483-46-4,59829-47-9,59829-48-0,70774-01-5,70774-02-6,92077-40-2,92077-41-3,92077-42-4,92077-43-5,92077-49-1,92077-50-4,114182-97-7,114183-07-2) → (3aR,4R,5R,6aS)-4-((E)-3-Hydroxy-oct-1-enyl)-hexahydro-cyclopenta[b]furan-2,5-diol (51388-75-1,59829-49-1,59829-50-4,59829-51-5,59829-52-6,85550-76-1,85550-82-9,136235-23-9,136235-24-0)

Guidance literature:

With hydrogenchloride; In water; acetonitrile; for 3h;

Reference yield: 98.0%

(E)-(S)-1-[(3aR,4R,5R,6aS)-5-(tert-Butyl-dimethyl-silanyloxy)-2-ethoxy-hexahydro-cyclopenta[b]furan-4-yl]-oct-1-en-3-ol (104015-26-1,136235-22-8) → (3aR,4R,5R,6a5)-4-[(E,3S)-3-Hydroxy-1-octenyl]perhydrocyclopenta[b]fura n-2,5-diol (51388-75-1,59829-49-1,59829-50-4,59829-51-5,59829-52-6,85550-76-1,85550-82-9,136235-23-9,136235-24-0)

Guidance literature:

With hydrogenchloride; In tetrahydrofuran; Ambient temperature;

DOI:10.1021/ja00280a043

Reference yield:

(-)-(1S,5R)-2-oxabicyclo[3.3.0]oct-6-en-3-one (26054-46-6) → (3aR,4R,5R,6a5)-4-[(E,3S)-3-Hydroxy-1-octenyl]perhydrocyclopenta[b]fura n-2,5-diol (51388-75-1,59829-49-1,59829-50-4,59829-51-5,59829-52-6,85550-76-1,85550-82-9,136235-23-9,136235-24-0)

Guidance literature:

Multi-step reaction with 5 steps

1.1: formic acid; sulfuric acid / 24 h / 80 °C

1.2: 2 h / 0 - 20 °C

2.1: [bis(acetoxy)iodo]benzene; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical / dichloromethane; N,N-dimethyl acetamide / 6 h / 20 °C

3.1: sodium hydride / tetrahydrofuran / 1 h / 0 °C / Inert atmosphere

3.2: 6 h / 0 - 20 °C / Inert atmosphere

4.1: (3aR)-1-methyl-3,3-diphenyl-tetrahydro-pyrrolo[1,2-c][1,3,2]oxazaborole; dimethylsulfide borane complex / tetrahydrofuran; toluene / 1 h / -30 °C

5.1: diisobutylaluminium hydride / dichloromethane / 2 h / -78 °C

With formic acid; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; [bis(acetoxy)iodo]benzene; dimethylsulfide borane complex; sulfuric acid; sodium hydride; diisobutylaluminium hydride; (3aR)-1-methyl-3,3-diphenyl-tetrahydro-pyrrolo[1,2-c][1,3,2]oxazaborole; In tetrahydrofuran; dichloromethane; N,N-dimethyl acetamide; toluene; 3.1: |Horner-Wadsworth-Emmons Olefination / 3.2: |Horner-Wadsworth-Emmons Olefination / 4.1: |Corey-Bakshi-Shibata Reduction;

DOI:10.1002/anie.201902371

upstream raw materials:

Acetic acid (3aR,4R,5R,6aS)-4-((E)-(S)-3-acetoxy-oct-1-enyl)-2-oxo-hexahydro-cyclopenta[b]furan-5-yl ester

(1R,2R,3R,5S)-3-Hydroxy-2-((E)-(S)-3-hydroxy-oct-1-enyl)-bicyclo[3.2.0]heptan-6-one

(E)-(S)-1-[(3aR,4R,5R,6aS)-5-(tert-Butyl-dimethyl-silanyloxy)-2-ethoxy-hexahydro-cyclopenta[b]furan-4-yl]-oct-1-en-3-ol

(1S,4R)-4-hydroxy-2-cyclopentenyl acetate

Downstream raw materials:

2-[(3aR,4R,5R,6aS)-5-Hydroxy-4-((E)-(S)-3-hydroxy-oct-1-enyl)-hexahydro-cyclopenta[b]furan-(2E)-ylidene]-1-phenyl-ethanone

2-[(3aR,4R,5R,6aS)-5-Hydroxy-4-((E)-(S)-3-hydroxy-oct-1-enyl)-hexahydro-cyclopenta[b]furan-2-yl]-1-phenyl-2-phenylsulfanyl-ethanone

1-[(3aR,4R,5R,6aS)-5-Hydroxy-4-((E)-(S)-3-hydroxy-oct-1-enyl)-hexahydro-cyclopenta[b]furan-2-yl]-1-phenylsulfanyl-propan-2-one

prostaglandin F_2α