<(5E,Z),(13E)>-15-(1-Fluorocyclohexyl)-11α,(15R)-dihydroxy-ω-pentanor-9a-carbaprostacyclin

Base Information

• Chemical Name: <(5E,Z),(13E)>-15-(1-Fluorocyclohexyl)-11α,(15R)-dihydroxy-ω-pentanor-9a-carbaprostacyclin
• CAS No.: 117169-36-5
• Molecular Formula: C₂₂H₃₃FO₄
• Molecular Weight: 380.5
• Mol file: 117169-36-5.mol

Synonyms:

Chemical Property of <(5E,Z),(13E)>-15-(1-Fluorocyclohexyl)-11α,(15R)-dihydroxy-ω-pentanor-9a-carbaprostacyclin

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of <(5E,Z),(13E)>-15-(1-Fluorocyclohexyl)-11α,(15R)-dihydroxy-ω-pentanor-9a-carbaprostacyclin

There total 20 articles about <(5E,Z),(13E)>-15-(1-Fluorocyclohexyl)-11α,(15R)-dihydroxy-ω-pentanor-9a-carbaprostacyclin 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:

1-oxaspiro<2,5>octane-2-carboxylic acid nitrile (36929-66-5,500899-63-8,500899-64-9) → <(5E,Z),(13E)>-15-(1-Fluorocyclohexyl)-11α,(15S)-dihydroxy-ω-pentanor-9a-carbaprostacyclin (117169-36-5,117248-68-7,117248-69-8,117248-70-1)

Guidance literature:

Multi-step reaction with 9 steps

1: 86 percent / 70percent HF / CH₂Cl₂; pyridine / 1.) 0 deg C, 1 h, 2.) room temp., 1 h

2: 74 percent / NaBH₄ / propan-2-ol; H₂O / 1 h / 0 °C

3: 59 percent / Jones reagent / acetone / 0 °C

4: 79 percent / diethyl ether / 5 °C

5: 1.) BuLi / 1.) hexane, THF, -70 deg C, 15 min, 2.) -70 deg C, 1 h; room temp., 1 h

6: 1.) NaH / 1.) THF, 30 min, 2.) -40 deg C, 1 h; room temp., 1 h

7: NaBH₄ / methanol / 0.17 h / Ambient temperature

8: aq. (CO₂H)2 / acetone / 40 °C

9: 1.) t-BuOK / 1.) DMSO, 15 min, 2.) 20 deg C, 2 h

With sodium tetrahydroborate; n-butyllithium; jones reagent; hydrogen fluoride; potassium tert-butylate; oxalic acid; sodium hydride; In pyridine; methanol; diethyl ether; dichloromethane; water; isopropyl alcohol; acetone;

DOI:10.1055/s-1988-27551

Reference yield:

1-oxaspiro<2,5>octane-2-carboxylic acid nitrile (36929-66-5,500899-63-8,500899-64-9) → <(5E,Z),(13E)>-15-(1-Fluorocyclohexyl)-11α,(15R)-dihydroxy-ω-pentanor-9a-carbaprostacyclin (117169-36-5,117248-68-7,117248-69-8,117248-70-1)

Guidance literature:

Multi-step reaction with 9 steps

1: 86 percent / 70percent HF / CH₂Cl₂; pyridine / 1.) 0 deg C, 1 h, 2.) room temp., 1 h

2: 74 percent / NaBH₄ / propan-2-ol; H₂O / 1 h / 0 °C

3: 59 percent / Jones reagent / acetone / 0 °C

4: 79 percent / diethyl ether / 5 °C

5: 1.) BuLi / 1.) hexane, THF, -70 deg C, 15 min, 2.) -70 deg C, 1 h; room temp., 1 h

6: 1.) NaH / 1.) THF, 30 min, 2.) -40 deg C, 1 h; room temp., 1 h

7: NaBH₄ / methanol / 0.17 h / Ambient temperature

8: aq. (CO₂H)2 / acetone / 40 °C

9: 1.) t-BuOK / 1.) DMSO, 15 min, 2.) 20 degC, 2 h

With sodium tetrahydroborate; n-butyllithium; jones reagent; hydrogen fluoride; potassium tert-butylate; oxalic acid; sodium hydride; In pyridine; methanol; diethyl ether; dichloromethane; water; isopropyl alcohol; acetone;

DOI:10.1055/s-1988-27551

Reference yield:

α-(1-Fluorocyclohexyl)-α-hydroxyacetonitrile (699-43-4) → <(5E,Z),(13E)>-15-(1-Fluorocyclohexyl)-11α,(15S)-dihydroxy-ω-pentanor-9a-carbaprostacyclin (117169-36-5,117248-68-7,117248-69-8,117248-70-1)

Guidance literature:

Multi-step reaction with 8 steps

1: 74 percent / NaBH₄ / propan-2-ol; H₂O / 1 h / 0 °C

2: 59 percent / Jones reagent / acetone / 0 °C

3: 79 percent / diethyl ether / 5 °C

4: 1.) BuLi / 1.) hexane, THF, -70 deg C, 15 min, 2.) -70 deg C, 1 h; room temp., 1 h

5: 1.) NaH / 1.) THF, 30 min, 2.) -40 deg C, 1 h; room temp., 1 h

6: NaBH₄ / methanol / 0.17 h / Ambient temperature

7: aq. (CO₂H)2 / acetone / 40 °C

8: 1.) t-BuOK / 1.) DMSO, 15 min, 2.) 20 deg C, 2 h

With sodium tetrahydroborate; n-butyllithium; jones reagent; potassium tert-butylate; oxalic acid; sodium hydride; In methanol; diethyl ether; water; isopropyl alcohol; acetone;

DOI:10.1055/s-1988-27551

upstream raw materials:

(4-carboxybutyl)triphenylphosphonium bromide

1-exo-<3-(1-Fluorocyclohexyl)-3(S)-hydroxy-(E)-1-propenyl>-2-endo-hydroxy-5-oxooctahydropentalene

1-oxaspiro<2,5>octane-2-carboxylic acid nitrile

α-(1-Fluorocyclohexyl)-α-hydroxyacetonitrile

Refernces