{(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

Base Information

• Chemical Name: {(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
• CAS No.: 208389-26-8
• Molecular Formula: C₄₃H₆₄O₆
• Molecular Weight: 676.978

Synonyms:

Chemical Property of {(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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
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Useful:

Technology Process of {(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

There total 17 articles about {(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 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,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 (208389-26-8)

Guidance literature:

Multi-step reaction with 13 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: 2.) pyridinium p-toluenesulfonate / 1.) THF, -62 deg C, 7 d; 2.) MeOH, r.t., 16 h

12: pyridinium p-toluenesulfonate / CH₂Cl₂ / Ambient temperature

13: 1.) (R,R)-bis(phenylethyl)ammonium chloride, nBuLi; 3.) sat.aq NaHCO₃ / 1.) THF, hexanes, -78 deg C, r.t.; 2.) -105 deg C, THF, 30 min; 3.) -78 deg C

With pyridine; dichloro bis(acetonitrile) palladium(II); sodium hydroxide; n-butyllithium; zinc(II) tetrahydroborate; oxalyl dichloride; boron trifluoride diethyl etherate; tetrabutyl ammonium fluoride; (R,R)-(+)-bis[alpha-methylbenzyl]amine hydrochloride; water; pyridinium p-toluenesulfonate; sodium hydrogencarbonate; 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,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 (208389-26-8)

Guidance literature:

Multi-step reaction with 4 steps

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

2: 2.) pyridinium p-toluenesulfonate / 1.) THF, -62 deg C, 7 d; 2.) MeOH, r.t., 16 h

3: pyridinium p-toluenesulfonate / CH₂Cl₂ / Ambient temperature

4: 1.) (R,R)-bis(phenylethyl)ammonium chloride, nBuLi; 3.) sat.aq NaHCO₃ / 1.) THF, hexanes, -78 deg C, r.t.; 2.) -105 deg C, THF, 30 min; 3.) -78 deg C

With n-butyllithium; (R,R)-(+)-bis[alpha-methylbenzyl]amine hydrochloride; pyridinium p-toluenesulfonate; sodium hydrogencarbonate; In dichloromethane;

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

Reference yield:

Benzoic acid (1R,2R,3aR,5S,6aS)-5-(tert-butyl-diphenyl-silanyloxy)-1-((E)-(R)-3-hydroxy-oct-1-enyl)-octahydro-pentalen-2-yl ester (208389-16-6) → {(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 (208389-26-8)

Guidance literature:

Multi-step reaction with 8 steps

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

2: Bu₄NF / tetrahydrofuran / 16 h / Ambient temperature

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

4: NaOH / methanol / 16 h / Ambient temperature

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

6: 2.) pyridinium p-toluenesulfonate / 1.) THF, -62 deg C, 7 d; 2.) MeOH, r.t., 16 h

7: pyridinium p-toluenesulfonate / CH₂Cl₂ / Ambient temperature

8: 1.) (R,R)-bis(phenylethyl)ammonium chloride, nBuLi; 3.) sat.aq NaHCO₃ / 1.) THF, hexanes, -78 deg C, r.t.; 2.) -105 deg C, THF, 30 min; 3.) -78 deg C

With sodium hydroxide; n-butyllithium; oxalyl dichloride; tetrabutyl ammonium fluoride; (R,R)-(+)-bis[alpha-methylbenzyl]amine hydrochloride; water; pyridinium p-toluenesulfonate; sodium hydrogencarbonate; dimethyl sulfoxide; triethylamine; triphenylphosphine; diethylazodicarboxylate; In tetrahydrofuran; methanol; dichloromethane;

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

upstream raw materials:

[(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

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

(E)-2-Octenal

(-)-(1S,2R,3R,5R)-2-(3(S)-hydroxyoct-1(E)-enyl)-7-oxobicyclo<3.3.0>octan-3-ol

Downstream raw materials:

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

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