(+/-)-dimethanothromboxane A₂

Base Information

• Chemical Name: (+/-)-dimethanothromboxane A₂
• CAS No.: 73804-44-1
• Molecular Formula: C₂₂H₃₆O₃
• Molecular Weight: 348.526
• Mol file: 73804-44-1.mol

Synonyms:

Chemical Property of (+/-)-dimethanothromboxane A₂

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (+/-)-dimethanothromboxane A₂

There total 23 articles about (+/-)-dimethanothromboxane A₂ 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: 88.0%

methyl (2R*,3S*)-(Z)-((E)-3-hydroxy-1-octenyl)bicyclo<3.1.1>heptane-2-hept-5-enoate (73509-45-2,73543-46-1,73837-11-3,74034-54-1,74034-55-2,84171-72-2) → (+/-)-dimethanothromboxane A2 (73509-46-3,73543-47-2,73804-44-1,74034-56-3,74034-57-4,84171-73-3)

Guidance literature:

With potassium hydroxide; In ethanol; at 45 ℃; for 0.833333h;

DOI:10.1016/S0040-4020(01)88648-8

Reference yield:

(Z)-7-[(2S,3R)-3-((E)-(R)-3-Hydroxy-oct-1-enyl)-bicyclo[3.1.1]hept-2-yl]-hept-5-enoic acid methyl ester (73509-45-2,73543-46-1,73837-11-3,74034-54-1,74034-55-2,84171-72-2) → (Z)-7-[(2S,3R)-3-((E)-(R)-3-Hydroxy-oct-1-enyl)-bicyclo[3.1.1]hept-2-yl]-hept-5-enoic acid (73509-46-3,73543-47-2,73804-44-1,74034-56-3,74034-57-4,84171-73-3)

Guidance literature:

With potassium hydroxide; In ethanol; at 45 ℃; for 0.833333h;

DOI:10.1016/S0040-4020(01)88648-8

Reference yield:

1-tributylphosphoranylidene-2-heptanone (35563-52-1) → (Z)-7-[(2S,3R)-3-((E)-(R)-3-Hydroxy-oct-1-enyl)-bicyclo[3.1.1]hept-2-yl]-hept-5-enoic acid (73509-46-3,73543-47-2,73804-44-1,74034-56-3,74034-57-4,84171-73-3)

Guidance literature:

Multi-step reaction with 8 steps

1: 90 percent / diethyl ether / 24 h

2: 88 percent / NaBH₄ / methanol / 0.83 h / -40 °C

3: 94 percent / p-TsOH / CH₂Cl₂ / 0.33 h / 0 °C

4: DIBAL / toluene / 0.33 h / -50 °C

5: Et₃N, SO₃-pyridine / dimethylsulfoxide / 20 h

6: 1.) dimsylsodium / 1.) DMSO, 30 deg C, 1 h, 40 deg C, 1 h, 2.) ether

7: 32 percent / PPTS / methanol / 2 h / 55 °C

8: 5percent KOH / ethanol / 0.83 h / 45 °C

With potassium hydroxide; sodium tetrahydroborate; pyridine-SO₃ complex; dimsylsodium; pyridinium p-toluenesulfonate; diisobutylaluminium hydride; toluene-4-sulfonic acid; triethylamine; In methanol; diethyl ether; ethanol; dichloromethane; dimethyl sulfoxide; toluene;

DOI:10.1016/S0040-4020(01)88648-8

upstream raw materials:

2-formylbicyclo<3.1.1>hept-2-ene

cis-1,3-bis(cyanomethyl)cyclobutane

cis-1,3-bis(formylmethyl)cyclobutane

(Z)-7-[(2S,3R)-3-((E)-(R)-3-Hydroxy-oct-1-enyl)-bicyclo[3.1.1]hept-2-yl]-hept-5-enoic acid methyl ester