6,9a-methanoprostaglandin I₃

Base Information

• Chemical Name: 6,9a-methanoprostaglandin I₃
• CAS No.: 96244-05-2
• Molecular Formula: C₂₁H₃₂O₄
• Molecular Weight: 348.483
• Mol file: 96244-05-2.mol

Synonyms:

Chemical Property of 6,9a-methanoprostaglandin I₃

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 6,9a-methanoprostaglandin I₃

There total 21 articles about 6,9a-methanoprostaglandin I₃ 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:

(Z)-3-Hexen-1-ol (928-96-1) → (+/-)-6,9α-methanoprostaglandin I3 (71846-42-9,71884-27-0,89461-40-5,96244-05-2,96244-71-2,96244-85-8)

Guidance literature:

Multi-step reaction with 9 steps

1: 51.9 g / pyridine / 14 h / -10 °C

2: 36.8 g / NaI / acetone / 1 h / Heating

3: 52.7 g / acetonitrile / 17 h / Heating

4: 1.)sodium methyl sulfinylmethide / 1.) DMSO, 10 min, 2.) THF, -78 deg C, 30 min, then room temperature, 1 h

5: 1.) m-CPBA, 2.) (MeO)3P / 1.) methanol, -30 deg C, 1 h, 2.) -30 deg C to room temperature, then room temperature, over night

6: 78 mg / AcOH, water / 4 h / 40 °C

7: 176 mg / p-TsOH / CH₂Cl₂ / 0.5 h

8: 1.) sodium methyl sulfinylmethide / 1.) DMSO, 15 - 20 deg C, 30 min, 2.) DMSO, room temperature, overnight

9: 21 mg / AcOH, water / Ambient temperature

With pyridine; dimsylsodium; water; acetic acid; 3-chloro-benzenecarboperoxoic acid; sodium iodide; phosphorous acid trimethyl ester; toluene-4-sulfonic acid; In dichloromethane; acetone; acetonitrile;

DOI:10.1016/S0040-4020(01)82339-5

Reference yield:

(Z)-3-hexenyl iodide (21676-03-9) → (+/-)-6,9α-methanoprostaglandin I3 (71846-42-9,71884-27-0,89461-40-5,96244-05-2,96244-71-2,96244-85-8)

Guidance literature:

Multi-step reaction with 7 steps

1: 52.7 g / acetonitrile / 17 h / Heating

2: 1.)sodium methyl sulfinylmethide / 1.) DMSO, 10 min, 2.) THF, -78 deg C, 30 min, then room temperature, 1 h

3: 1.) m-CPBA, 2.) (MeO)3P / 1.) methanol, -30 deg C, 1 h, 2.) -30 deg C to room temperature, then room temperature, over night

4: 78 mg / AcOH, water / 4 h / 40 °C

5: 176 mg / p-TsOH / CH₂Cl₂ / 0.5 h

6: 1.) sodium methyl sulfinylmethide / 1.) DMSO, 15 - 20 deg C, 30 min, 2.) DMSO, room temperature, overnight

7: 21 mg / AcOH, water / Ambient temperature

With dimsylsodium; water; acetic acid; 3-chloro-benzenecarboperoxoic acid; phosphorous acid trimethyl ester; toluene-4-sulfonic acid; In dichloromethane; acetonitrile;

DOI:10.1016/S0040-4020(01)82339-5

Reference yield:

(Z)-3-hexenyl-1-tosylate (34019-85-7) → (+/-)-6,9α-methanoprostaglandin I3 (71846-42-9,71884-27-0,89461-40-5,96244-05-2,96244-71-2,96244-85-8)

Guidance literature:

Multi-step reaction with 8 steps

1: 36.8 g / NaI / acetone / 1 h / Heating

2: 52.7 g / acetonitrile / 17 h / Heating

3: 1.)sodium methyl sulfinylmethide / 1.) DMSO, 10 min, 2.) THF, -78 deg C, 30 min, then room temperature, 1 h

4: 1.) m-CPBA, 2.) (MeO)3P / 1.) methanol, -30 deg C, 1 h, 2.) -30 deg C to room temperature, then room temperature, over night

5: 78 mg / AcOH, water / 4 h / 40 °C

6: 176 mg / p-TsOH / CH₂Cl₂ / 0.5 h

7: 1.) sodium methyl sulfinylmethide / 1.) DMSO, 15 - 20 deg C, 30 min, 2.) DMSO, room temperature, overnight

8: 21 mg / AcOH, water / Ambient temperature

With dimsylsodium; water; acetic acid; 3-chloro-benzenecarboperoxoic acid; sodium iodide; phosphorous acid trimethyl ester; toluene-4-sulfonic acid; In dichloromethane; acetone; acetonitrile;

DOI:10.1016/S0040-4020(01)82339-5

upstream raw materials:

(+/-)-6,9α-methanoprostaglandin I3 11,15-bis(tetrahydropyran-2-yl)ether

(Z)-3-Hexen-1-ol

(Z)-3-hexenyl iodide

(Z)-3-hexenyl-1-tosylate