5-[(3aS,5R,6R,6aS)-5-Hydroxy-6-((E)-(R)-3-hydroxy-oct-1-enyl)-1,3a,4,5,6,6a-hexahydro-pentalen-2-yl]-pentanoic acid

Base Information

• Chemical Name: 5-[(3aS,5R,6R,6aS)-5-Hydroxy-6-((E)-(R)-3-hydroxy-oct-1-enyl)-1,3a,4,5,6,6a-hexahydro-pentalen-2-yl]-pentanoic acid
• CAS No.: 119238-07-2
• Molecular Formula: C₂₁H₃₄O₄
• Molecular Weight: 350.499
• Mol file: 119238-07-2.mol

Synonyms:

Chemical Property of 5-[(3aS,5R,6R,6aS)-5-Hydroxy-6-((E)-(R)-3-hydroxy-oct-1-enyl)-1,3a,4,5,6,6a-hexahydro-pentalen-2-yl]-pentanoic acid

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 5-[(3aS,5R,6R,6aS)-5-Hydroxy-6-((E)-(R)-3-hydroxy-oct-1-enyl)-1,3a,4,5,6,6a-hexahydro-pentalen-2-yl]-pentanoic acid

There total 71 articles about 5-[(3aS,5R,6R,6aS)-5-Hydroxy-6-((E)-(R)-3-hydroxy-oct-1-enyl)-1,3a,4,5,6,6a-hexahydro-pentalen-2-yl]-pentanoic 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: 80.0%

5-{(3aR,5S,6S,6aR)-5-(Tetrahydro-pyran-2-yloxy)-6-[(E)-(R)-3-(tetrahydro-pyran-2-yloxy)-oct-1-enyl]-1,3a,4,5,6,6a-hexahydro-pentalen-2-yl}-pentanoic acid → dl-9(O)-methano-Δ6(9α)PGI1 (88911-35-7,88931-52-6,88931-59-3,99946-24-4,119238-07-2,125135-54-8,139757-12-3)

Guidance literature:

With camphor-10-sulfonic acid; In water; acetone; at 40 ℃; for 3h;

DOI:10.1248/cpb.32.2866

Reference yield:

isocarbacyclin (88931-51-5) → (+)-9(O)-methano-Δ6(9α)-PGI1 (88911-35-7,88931-52-6,88931-59-3,99946-24-4,119238-07-2,125135-54-8,139757-12-3)

Guidance literature:

With sodium hydroxide; In methanol; water; Yield given;

DOI:10.1016/S0040-4039(01)80103-9

Reference yield:

(2R*,3S*,4R*)-2-allyl-4-tert-butyldimethylsilyloxy-3-(3-tert-butyldimethylsilyloxy-(E)-1-octenyl)-1-methylenecyclopentane (95205-53-1,95273-37-3,98676-75-6) → dl-9(O)-methano-Δ6(9α)PGI1 (88911-35-7,88931-52-6,88931-59-3,99946-24-4,119238-07-2,125135-54-8,139757-12-3)

Guidance literature:

Multi-step reaction with 8 steps

1: 1.) 9-borabicyclo<3.3.1>nonane, 2.) aq. NaOH, H₂O₂

2: 2.) dibenzylammonium trifluoroacetate / 1.) by Swern oxidation, 2.) benzene, 70 deg C

3: 88 percent / diisobutylaluminum hydride / toluene; hexane / 1.5 h / -78 °C

4: 99 percent / 4-dimethylaminopyridine / pyridine / 0.5 h / 23 °C

5: 1.) cuprous iodide, 2.) 9-borabicyclo<3.3.1>nonane, 3.) 6 N aq. NaOH, 30 percent H₂O₂ / 1.) ether/hexane, -78 deg C, 1h then 23 deg C, 20 min, 2.) THF, 0 deg C, 3 h then 23 deg C, 1 h, 3.) THF, 50 deg C, 1 h

6: 87 percent / pyridinium chlorochromate, sodium acetate / CH₂Cl₂ / 2 h / 23 °C

7: 77 percent / silver oxide, AgNO₃, 5 N aq. NaOH / methanol; tetrahydrofuran / 0.42 h / 45 °C

8: tetra-n-butylammonium fluoride / tetrahydrofuran / 48 h / 23 °C

With sodium hydroxide; copper(l) iodide; 9-borabicyclo[3.3.1]nonane dimer; tetrabutyl ammonium fluoride; dihydrogen peroxide; sodium acetate; diisobutylaluminium hydride; silver nitrate; pyridinium chlorochromate; silver(l) oxide; dibenzylammonium trifluoroacetate salt; dmap; In tetrahydrofuran; pyridine; methanol; hexane; dichloromethane; toluene;

DOI:10.1248/cpb.37.586

upstream raw materials:

5-[(3aR,5S,6S,6aR)-5-Hydroxy-6-((E)-(R)-3-hydroxy-oct-1-enyl)-1,3a,4,5,6,6a-hexahydro-pentalen-2-yl]-pentanoic acid methyl ester

5-{(3aR,5S,6S,6aR)-5-(tert-Butyl-dimethyl-silanyloxy)-6-[(E)-(R)-3-(tert-butyl-dimethyl-silanyloxy)-oct-1-enyl]-1,3a,4,5,6,6a-hexahydro-pentalen-2-yl}-pentanoic acid

(1R^*,5S^*,6R^*,7R^*)-7-tert-butyldimethylsilyloxy-6-(3-tert-butyldimethylsilyloxy-(E)-1-octenyl)bicyclo<3.3.0>oct-2-ene-3-pentanoic acid