[(3aS,4R,5R,6aS)-5-(Tetrahydro-pyran-2-yloxy)-4-[(E)-(S)-3-(tetrahydro-pyran-2-yloxy)-oct-1-enyl]-hexahydro-pentalen-(2Z)-ylidene]-acetic acid (1S,2R)-2-(1-methyl-1-phenyl-ethyl)-cyclohexyl ester

Base Information

• Chemical Name: [(3aS,4R,5R,6aS)-5-(Tetrahydro-pyran-2-yloxy)-4-[(E)-(S)-3-(tetrahydro-pyran-2-yloxy)-oct-1-enyl]-hexahydro-pentalen-(2Z)-ylidene]-acetic acid (1S,2R)-2-(1-methyl-1-phenyl-ethyl)-cyclohexyl ester
• CAS No.: 208389-24-6
• Molecular Formula: C₄₃H₆₄O₆
• Molecular Weight: 676.978
• Mol file: 208389-24-6.mol

Synonyms:

Chemical Property of [(3aS,4R,5R,6aS)-5-(Tetrahydro-pyran-2-yloxy)-4-[(E)-(S)-3-(tetrahydro-pyran-2-yloxy)-oct-1-enyl]-hexahydro-pentalen-(2Z)-ylidene]-acetic acid (1S,2R)-2-(1-methyl-1-phenyl-ethyl)-cyclohexyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of [(3aS,4R,5R,6aS)-5-(Tetrahydro-pyran-2-yloxy)-4-[(E)-(S)-3-(tetrahydro-pyran-2-yloxy)-oct-1-enyl]-hexahydro-pentalen-(2Z)-ylidene]-acetic acid (1S,2R)-2-(1-methyl-1-phenyl-ethyl)-cyclohexyl ester

There total 14 articles about [(3aS,4R,5R,6aS)-5-(Tetrahydro-pyran-2-yloxy)-4-[(E)-(S)-3-(tetrahydro-pyran-2-yloxy)-oct-1-enyl]-hexahydro-pentalen-(2Z)-ylidene]-acetic acid (1S,2R)-2-(1-methyl-1-phenyl-ethyl)-cyclohexyl ester 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:

(E)-2-Octenal (2548-87-0) → [(3aS,4R,5R,6aS)-5-(Tetrahydro-pyran-2-yloxy)-4-[(E)-(S)-3-(tetrahydro-pyran-2-yloxy)-oct-1-enyl]-hexahydro-pentalen-(2Z)-ylidene]-acetic acid (1S,2R)-2-(1-methyl-1-phenyl-ethyl)-cyclohexyl ester (208389-24-6)

Guidance literature:

Multi-step reaction with 11 steps

1: 1.) Et₂O*BF₃; 2.) aq AcOH / 1.) CH₂Cl₂, -78 deg C, 1 h; 2.) THF, r.t., 12 h

2: 1.) pyridine; 2.) Zn(BH₄)2 / 1.) THF, 16 h, r.t.; 2.) ether, -30 deg C, 6 h

3: pyridine / 3 h / 0 °C

4: Pd(MeCN)2Cl₂ / tetrahydrofuran / 16 h / Ambient temperature

5: 1percent K₂CO₃ / methanol / 1.67 h / Ambient temperature

6: PPh₃, diethylazodicarboxylate / tetrahydrofuran / 1 h / -30 °C

7: Bu₄NF / tetrahydrofuran / 16 h / Ambient temperature

8: 1.) (COCl)2, DMSO; 2.) NEt₃, water / 1.) CH₂Cl₂, -60 deg C, 10 min, 15 min; 2.) r.t.

9: NaOH / methanol / 16 h / Ambient temperature

10: pyridinium p-toluenesulfonate / CH₂Cl₂ / 16 h / Ambient temperature

11: tetrahydrofuran / 168 h / -62 °C

With pyridine; dichloro bis(acetonitrile) palladium(II); sodium hydroxide; zinc(II) tetrahydroborate; oxalyl dichloride; boron trifluoride diethyl etherate; tetrabutyl ammonium fluoride; water; pyridinium p-toluenesulfonate; potassium carbonate; acetic acid; dimethyl sulfoxide; triethylamine; triphenylphosphine; diethylazodicarboxylate; In tetrahydrofuran; pyridine; methanol; dichloromethane;

DOI:10.1002/(SICI)1099-0690(199805)1998:5<805::AID-EJOC805>3.0.CO;2-R

Reference yield:

(-)-(1S,2R,3R,5R)-2-(3(S)-hydroxyoct-1(E)-enyl)-7-oxobicyclo<3.3.0>octan-3-ol (69552-54-1) → [(3aS,4R,5R,6aS)-5-(Tetrahydro-pyran-2-yloxy)-4-[(E)-(S)-3-(tetrahydro-pyran-2-yloxy)-oct-1-enyl]-hexahydro-pentalen-(2Z)-ylidene]-acetic acid (1S,2R)-2-(1-methyl-1-phenyl-ethyl)-cyclohexyl ester (208389-24-6)

Guidance literature:

Multi-step reaction with 2 steps

1: pyridinium p-toluenesulfonate / CH₂Cl₂ / 16 h / Ambient temperature

2: tetrahydrofuran / 168 h / -62 °C

With pyridinium p-toluenesulfonate; In tetrahydrofuran; dichloromethane;

DOI:10.1002/(SICI)1099-0690(199805)1998:5<805::AID-EJOC805>3.0.CO;2-R

Reference yield:

[3aS-(3aα,4α(1E,3R*),5β,6aα)]-5-benzoyloxy-4-(3-benzoyloxy-1-octenyl)hexahydro-2(1H)-pentalenone (71846-09-8) → [(3aS,4R,5R,6aS)-5-(Tetrahydro-pyran-2-yloxy)-4-[(E)-(S)-3-(tetrahydro-pyran-2-yloxy)-oct-1-enyl]-hexahydro-pentalen-(2Z)-ylidene]-acetic acid (1S,2R)-2-(1-methyl-1-phenyl-ethyl)-cyclohexyl ester (208389-24-6)

Guidance literature:

Multi-step reaction with 3 steps

1: NaOH / methanol / 16 h / Ambient temperature

2: pyridinium p-toluenesulfonate / CH₂Cl₂ / 16 h / Ambient temperature

3: tetrahydrofuran / 168 h / -62 °C

With sodium hydroxide; pyridinium p-toluenesulfonate; In tetrahydrofuran; methanol; dichloromethane;

DOI:10.1002/(SICI)1099-0690(199805)1998:5<805::AID-EJOC805>3.0.CO;2-R

upstream raw materials:

3,4-dihydro-2H-pyran

[(3aS,4R,5R,6aS)-5-Hydroxy-4-((E)-(S)-3-hydroxy-oct-1-enyl)-hexahydro-pentalen-(2Z)-ylidene]-acetic acid (1S,2R)-2-(1-methyl-1-phenyl-ethyl)-cyclohexyl ester

(1S,2R,3R,5R)-7-oxo-3-(tetrahydropyran-2-yl)oxy-2-[3(S)-(tetrahydropyran-2-yl)oxy-E-1-octenyl]bicyclo[3.3.0]octane

(E)-2-Octenal

Downstream raw materials:

{(3aR,4R,5R,6aS)-5-(Tetrahydro-pyran-2-yloxy)-4-[(E)-(S)-3-(tetrahydro-pyran-2-yloxy)-oct-1-enyl]-1,3a,4,5,6,6a-hexahydro-pentalen-2-yl}-acetic acid (1S,2R)-2-(1-methyl-1-phenyl-ethyl)-cyclohexyl ester

{(3aS,5R,6R,6aS)-5-(Tetrahydro-pyran-2-yloxy)-6-[(E)-(S)-3-(tetrahydro-pyran-2-yloxy)-oct-1-enyl]-1,3a,4,5,6,6a-hexahydro-pentalen-2-yl}-acetic acid (1S,2R)-2-(1-methyl-1-phenyl-ethyl)-cyclohexyl ester

(+)-[2-[(2R,3aS,4R,5R,6aS)-octahydro-5-hydroxy-4-[(E)-(3S,5S)-3-hydroxy-5-methyl-1-nonenyl]-2-pentalenyl]ethoxy]acetic acid