3-Oxahomoisocarbacyclin

Base Information

• Chemical Name: 3-Oxahomoisocarbacyclin
• CAS No.: 127127-92-8
• Molecular Formula: C25H34 O6
• Molecular Weight: 430.5339
• Mol file: 127127-92-8.mol

Synonyms:3-oxahomoisocarbacyclin

Chemical Property of 3-Oxahomoisocarbacyclin

Chemical Property:

• Vapor Pressure: 4.09E-16mmHg at 25°C
• Boiling Point: 617.7°Cat760mmHg
• Flash Point: 206.2°C
• PSA: 96.22000
• Density: 1.222g/cm³
• LogP: 3.58580
• XLogP3: 2.9
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 10
• Exact Mass: 430.23553880
• Heavy Atom Count: 31
• Complexity: 648

Purity/Quality:

99%min ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C)(C(C=CC1C2CCC(=CC2CC1O)CCOCC(=O)O)O)OC3=CC=CC=C3
• Isomeric SMILES: CC(C)([C@@H](/C=C/[C@@H]1[C@@H]2CCC(=C[C@@H]2C[C@@H]1O)CCOCC(=O)O)O)OC3=CC=CC=C3

Technology Process of 3-Oxahomoisocarbacyclin

There total 19 articles about 3-Oxahomoisocarbacyclin 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: 90.0%

{2-[(1R,2R,3aS,7aS)-2-Hydroxy-1-((E)-(R)-3-hydroxy-4-methyl-4-phenoxy-pent-1-enyl)-2,3,3a,6,7,7a-hexahydro-1H-inden-5-yl]-ethoxy}-acetic acid tert-butyl ester (127127-90-6) → {2-[(1R,2R,3aS,7aS)-2-Hydroxy-1-((E)-(R)-3-hydroxy-4-methyl-4-phenoxy-pent-1-enyl)-2,3,3a,6,7,7a-hexahydro-1H-inden-5-yl]-ethoxy}-acetic acid (127127-92-8,117028-28-1)

Guidance literature:

With potassium hydroxide; In methanol;

DOI:10.1248/cpb.37.1647

Reference yield:

(3aR,4S,5R,6aS)-4-({[dimethyl(2-methyl-2-propanyl)silyl]oxy}methyl)-5-(tetrahydro-2H-pyran-2-yloxy)hexahydro-2H-cyclopenta[b]furan-2-one (65025-95-8) → {2-[(1R,2R,3aS,7aS)-2-Hydroxy-1-((E)-(R)-3-hydroxy-4-methyl-4-phenoxy-pent-1-enyl)-2,3,3a,6,7,7a-hexahydro-1H-inden-5-yl]-ethoxy}-acetic acid (127127-92-8,117028-28-1)

Guidance literature:

Multi-step reaction with 18 steps

1: DIBAH / toluene / -78 °C

2: toluene / 60 °C

3: H₂ / 10percent Pd/C / methanol / Ambient temperature

4: (COCl)2, DMSO, Et₃N / CH₂Cl₂ / -78 °C

5: Zn, TiCl₄ / Ambient temperature

6: 100 percent / Siam₂BH / tetrahydrofuran / 0 °C

7: LiAlH₄ / tetrahydrofuran / 0 °C

8: (COCl)2, DMSO, Et₃N / CH₂Cl₂ / -78 °C

9: (PhCH₂)2NH₂(+)*TFA(-) / benzene / 60 °C

10: tBuOK / tetrahydrofuran / Ambient temperature

11: 9-BBN / tetrahydrofuran / 0 °C

12: 50percent aq. NaOH / Bu₄N*HSO₄ / CH₂Cl₂ / 40 °C

13: Bu₄NF / tetrahydrofuran / Ambient temperature

14: SO₃*Py, Et₃N / dimethylsulfoxide / Ambient temperature

15: 90 percent / NaH / tetrahydrofuran / Ambient temperature

16: 100 percent / AcOH / tetrahydrofuran; H₂O / 50 °C

17: 79 percent / diisobutylaluminum 2,6-di-t-butyl-4-methylphenoxide / toluene / -78 - -20 °C

18: 90 percent / 7percent aq. KOH / methanol

With potassium hydroxide; sodium hydroxide; lithium aluminium tetrahydride; 9-borabicyclo[3.3.1]nonane dimer; oxalyl dichloride; pyridine-SO₃ complex; potassium tert-butylate; tetrabutyl ammonium fluoride; hydrogen; bis-(1,2-dimethylpropyl)borane; titanium tetrachloride; sodium hydride; diisobutylaluminium hydride; diisobutyl(2,6-di-tert-butyl-4- methylphenoxy)aluminum; acetic acid; dimethyl sulfoxide; triethylamine; zinc; dibenzylammonium trifluoroacetate salt; palladium on activated charcoal; tetra(n-butyl)ammonium hydrogensulfate; In tetrahydrofuran; methanol; dichloromethane; water; dimethyl sulfoxide; toluene; benzene;

DOI:10.1248/cpb.37.1647

Reference yield:

[(1R,2S,3R,5S)-2-(tert-Butyl-dimethyl-silanyloxymethyl)-5-hydroxy-3-(tetrahydro-pyran-2-yloxy)-cyclopentyl]-acetaldehyde → {2-[(1R,2R,3aS,7aS)-2-Hydroxy-1-((E)-(R)-3-hydroxy-4-methyl-4-phenoxy-pent-1-enyl)-2,3,3a,6,7,7a-hexahydro-1H-inden-5-yl]-ethoxy}-acetic acid (127127-92-8,117028-28-1)

Guidance literature:

Multi-step reaction with 17 steps

1: toluene / 60 °C

2: H₂ / 10percent Pd/C / methanol / Ambient temperature

3: (COCl)2, DMSO, Et₃N / CH₂Cl₂ / -78 °C

4: Zn, TiCl₄ / Ambient temperature

5: 100 percent / Siam₂BH / tetrahydrofuran / 0 °C

6: LiAlH₄ / tetrahydrofuran / 0 °C

7: (COCl)2, DMSO, Et₃N / CH₂Cl₂ / -78 °C

8: (PhCH₂)2NH₂(+)*TFA(-) / benzene / 60 °C

9: tBuOK / tetrahydrofuran / Ambient temperature

10: 9-BBN / tetrahydrofuran / 0 °C

11: 50percent aq. NaOH / Bu₄N*HSO₄ / CH₂Cl₂ / 40 °C

12: Bu₄NF / tetrahydrofuran / Ambient temperature

13: SO₃*Py, Et₃N / dimethylsulfoxide / Ambient temperature

14: 90 percent / NaH / tetrahydrofuran / Ambient temperature

15: 100 percent / AcOH / tetrahydrofuran; H₂O / 50 °C

16: 79 percent / diisobutylaluminum 2,6-di-t-butyl-4-methylphenoxide / toluene / -78 - -20 °C

17: 90 percent / 7percent aq. KOH / methanol

With potassium hydroxide; sodium hydroxide; lithium aluminium tetrahydride; 9-borabicyclo[3.3.1]nonane dimer; oxalyl dichloride; pyridine-SO₃ complex; potassium tert-butylate; tetrabutyl ammonium fluoride; hydrogen; bis-(1,2-dimethylpropyl)borane; titanium tetrachloride; sodium hydride; diisobutyl(2,6-di-tert-butyl-4- methylphenoxy)aluminum; acetic acid; dimethyl sulfoxide; triethylamine; zinc; dibenzylammonium trifluoroacetate salt; palladium on activated charcoal; tetra(n-butyl)ammonium hydrogensulfate; In tetrahydrofuran; methanol; dichloromethane; water; dimethyl sulfoxide; toluene; benzene;

DOI:10.1248/cpb.37.1647

upstream raw materials:

{2-[(1R,2R,3aS,7aS)-2-Hydroxy-1-((E)-(R)-3-hydroxy-4-methyl-4-phenoxy-pent-1-enyl)-2,3,3a,6,7,7a-hexahydro-1H-inden-5-yl]-ethoxy}-acetic acid tert-butyl ester

(3aR,4S,5R,6aS)-4-({[dimethyl(2-methyl-2-propanyl)silyl]oxy}methyl)-5-(tetrahydro-2H-pyran-2-yloxy)hexahydro-2H-cyclopenta[b]furan-2-one

(1S,2R,3aS,7aS)-1-(tert-Butyl-dimethyl-silanyloxymethyl)-2-(tetrahydro-pyran-2-yloxy)-2,3,3a,6,7,7a-hexahydro-1H-indene-5-carbaldehyde

{2-[(1S,2R,3aS,7aS)-1-Hydroxymethyl-2-(tetrahydro-pyran-2-yloxy)-2,3,3a,6,7,7a-hexahydro-1H-inden-5-yl]-ethoxy}-acetic acid tert-butyl ester

Refernces