(3aS)-3aβ,4,5,5a,6,9β,10,10aβ-Octahydro-6β-hydroxy-3a,5aα-dimethyl-1-isopropyl-6,9-epoxycyclohept[e]indene-8-methanol

Base Information

• Chemical Name: (3aS)-3aβ,4,5,5a,6,9β,10,10aβ-Octahydro-6β-hydroxy-3a,5aα-dimethyl-1-isopropyl-6,9-epoxycyclohept[e]indene-8-methanol
• CAS No.: 38459-01-7
• Molecular Formula: C20H28O3
• Molecular Weight: 316.43452
• Mol file: 38459-01-7.mol

Synonyms:

Chemical Property of (3aS)-3aβ,4,5,5a,6,9β,10,10aβ-Octahydro-6β-hydroxy-3a,5aα-dimethyl-1-isopropyl-6,9-epoxycyclohept[e]indene-8-methanol

Chemical Property:

• PSA: 49.69000
• LogP: 3.34120

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (3aS)-3aβ,4,5,5a,6,9β,10,10aβ-Octahydro-6β-hydroxy-3a,5aα-dimethyl-1-isopropyl-6,9-epoxycyclohept[e]indene-8-methanol

There total 13 articles about (3aS)-3aβ,4,5,5a,6,9β,10,10aβ-Octahydro-6β-hydroxy-3a,5aα-dimethyl-1-isopropyl-6,9-epoxycyclohept[e]indene-8-methanol 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%

COCHC2CH3CH2(CH2)2CCH3CH(CH2)2CHOCOCH3CCH2C2H4CH2 → allocyathin B3 (38459-01-7)

Guidance literature:

With perchloric acid; In tetrahydrofuran;

DOI:10.1021/ol006026c

Reference yield:

COCHC2CH3CH2(CH2)2CCH3CH(CH2)2CHOCOCH3CHOCOC6H5 (111251-69-5) → allocyathin B3 (38459-01-7)

Guidance literature:

Multi-step reaction with 13 steps

1.1: HCl / methanol; toluene / Heating

2.1: NBS / CH₂Cl₂ / -78 °C

3.1: Ph₃SnH; AIBN / benzene / Heating

4.1: 90 percent / H₂ / Pd-C / ethyl acetate

5.1: 75 percent / pyridinium 4-methylbenzenesulfonate / acetone; H₂O / 288 h

6.1: Ph₂PCl; pyridine / toluene

6.2: I₂

7.1: H₂ / Pd-C

8.1: NaOH / methanol / Heating

8.2: 85 percent / NMO; TPAP

9.1: 2,6-di tert-butyl-4-methylpyridine

10.1: 50 percent / Bu₃SnH; LiCl; Pd(Ph₃P)4 / tetrahydrofuran

11.1: NaN(TMS)2 / tetrahydrofuran / -78 °C

11.2: PhNTf₂ / tetrahydrofuran

11.3: 50 percent / DIEA; Pd(Ph₃P)4 / tetrahydrofuran

12.1: 50 percent / DIBAL-H

13.1: 80 percent / aq. HClO₄ / tetrahydrofuran

With pyridine; hydrogenchloride; sodium hydroxide; N-Bromosuccinimide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; perchloric acid; 2,6-di-tert-butyl-4-methylpyridine; 2,2'-azobis(isobutyronitrile); triphenylstannane; hydrogen; tri-n-butyl-tin hydride; sodium hexamethyldisilazane; pyridinium p-toluenesulfonate; diisobutylaluminium hydride; chloro-diphenylphosphine; lithium chloride; palladium on activated charcoal; In tetrahydrofuran; methanol; dichloromethane; water; ethyl acetate; acetone; toluene; benzene; 1.1: Methylation / 2.1: Addition / 3.1: Cyclization / 4.1: Hydrogenation / 5.1: demethylation / 6.1: Substitution / 6.2: Iodination / 7.1: Hydrogenation / 8.1: Isomerization / 8.2: Oxidation / 9.1: trifluoromethylsulfonylation / 10.1: Reduction / 11.1: deprotonation / 11.2: trifluoromethylsulfonylation / 11.3: Carbonylation / 12.1: Reduction / 13.1: Hydrolysis;

DOI:10.1021/ol006026c

Reference yield:

COCHC2CH3CH2(CH2)2CCH3CH(CH2)2CHOCOCH3CHOCOC6H5CH2 → allocyathin B3 (38459-01-7)

Guidance literature:

Multi-step reaction with 12 steps

1.1: NBS / CH₂Cl₂ / -78 °C

2.1: Ph₃SnH; AIBN / benzene / Heating

3.1: 90 percent / H₂ / Pd-C / ethyl acetate

4.1: 75 percent / pyridinium 4-methylbenzenesulfonate / acetone; H₂O / 288 h

5.1: Ph₂PCl; pyridine / toluene

5.2: I₂

6.1: H₂ / Pd-C

7.1: NaOH / methanol / Heating

7.2: 85 percent / NMO; TPAP

8.1: 2,6-di tert-butyl-4-methylpyridine

9.1: 50 percent / Bu₃SnH; LiCl; Pd(Ph₃P)4 / tetrahydrofuran

10.1: NaN(TMS)2 / tetrahydrofuran / -78 °C

10.2: PhNTf₂ / tetrahydrofuran

10.3: 50 percent / DIEA; Pd(Ph₃P)4 / tetrahydrofuran

11.1: 50 percent / DIBAL-H

12.1: 80 percent / aq. HClO₄ / tetrahydrofuran

With pyridine; sodium hydroxide; N-Bromosuccinimide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; perchloric acid; 2,6-di-tert-butyl-4-methylpyridine; 2,2'-azobis(isobutyronitrile); triphenylstannane; hydrogen; tri-n-butyl-tin hydride; sodium hexamethyldisilazane; pyridinium p-toluenesulfonate; diisobutylaluminium hydride; chloro-diphenylphosphine; lithium chloride; palladium on activated charcoal; In tetrahydrofuran; methanol; dichloromethane; water; ethyl acetate; acetone; toluene; benzene; 1.1: Addition / 2.1: Cyclization / 3.1: Hydrogenation / 4.1: demethylation / 5.1: Substitution / 5.2: Iodination / 6.1: Hydrogenation / 7.1: Isomerization / 7.2: Oxidation / 8.1: trifluoromethylsulfonylation / 9.1: Reduction / 10.1: deprotonation / 10.2: trifluoromethylsulfonylation / 10.3: Carbonylation / 11.1: Reduction / 12.1: Hydrolysis;

DOI:10.1021/ol006026c

upstream raw materials:

COCHC₂CH₃CH₂(CH₂)2CCH₃CH(CH₂)2CHOCOCH₃CHOCOC₆H₅