(+)-(3aS,5aR,6S,9bR)-6-(4-methoxybenzyloxy)-3,3a,4,5,5a,6,7,8-octahydro-3a,5a-dimethyl-2H-cyclopenta[a]naphthalen-1(9bH)-one

Base Information

• Chemical Name: (+)-(3aS,5aR,6S,9bR)-6-(4-methoxybenzyloxy)-3,3a,4,5,5a,6,7,8-octahydro-3a,5a-dimethyl-2H-cyclopenta[a]naphthalen-1(9bH)-one
• CAS No.: 824940-71-8
• Molecular Formula: C₂₃H₃₀O₃
• Molecular Weight: 354.489
• Mol file: 824940-71-8.mol

Synonyms:(+)-(3aS,5aR,6S,9bR)-6-(4-methoxybenzyloxy)-3,3a,4,5,5a,6,7,8-octahydro-3a,5a-dimethyl-2H-cyclopenta[a]naphthalen-1(9bH)-one

Chemical Property of (+)-(3aS,5aR,6S,9bR)-6-(4-methoxybenzyloxy)-3,3a,4,5,5a,6,7,8-octahydro-3a,5a-dimethyl-2H-cyclopenta[a]naphthalen-1(9bH)-one

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (+)-(3aS,5aR,6S,9bR)-6-(4-methoxybenzyloxy)-3,3a,4,5,5a,6,7,8-octahydro-3a,5a-dimethyl-2H-cyclopenta[a]naphthalen-1(9bH)-one

There total 17 articles about (+)-(3aS,5aR,6S,9bR)-6-(4-methoxybenzyloxy)-3,3a,4,5,5a,6,7,8-octahydro-3a,5a-dimethyl-2H-cyclopenta[a]naphthalen-1(9bH)-one 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: 71.0%

(+)-(3aS,5aS,6S,9aR,9bR)-6-(4-methoxybenzyloxy)-decahydro-9a-hydroxy-3a,5a-dimethyl-2H-cyclopenta[a]naphthalen-1(9bH)-one (824940-70-7) → (+)-(3aS,5aR,6S,9bR)-6-(4-methoxybenzyloxy)-3,3a,4,5,5a,6,7,8-octahydro-3a,5a-dimethyl-2H-cyclopenta[a]naphthalen-1(9bH)-one (824940-71-8) + (+)-(3aS,5aR,6S)-6-(4-methoxybenzyloxy)-2,3,3a,4,5,5a,6,7,8,9-decahydro-3a,5a-dimethyl-cyclopenta[a]naphthalen-1-one (824940-72-9)

Guidance literature:

With pyridine; thionyl chloride; In dichloromethane; at 0 - 20 ℃; for 2h;

DOI:10.1021/ol048010i

Reference yield:

(1S,3S)-2-benzyloxymethyl-2-methylcyclohexane-1,3-diol (619335-63-6) → (+)-(3aS,5aR,6S,9bR)-6-(4-methoxybenzyloxy)-3,3a,4,5,5a,6,7,8-octahydro-3a,5a-dimethyl-2H-cyclopenta[a]naphthalen-1(9bH)-one (824940-71-8)

Guidance literature:

Multi-step reaction with 12 steps

1.1: 100 percent / H₂ / Raney Ni / 12 h / 20 °C

2.1: 90 percent / CSA / CH₂Cl₂ / 2 h / 20 °C

3.1: 100 percent / DIPEA / 1 h / 20 °C

4.1: 97 percent / DIBAL-H / hexane / 4 h / 20 °C

5.1: 93 percent / PPh₃; I₂ / benzene / Heating

6.1: t-BuLi / diethyl ether; tetrahydrofuran / -78 °C

6.2: 79 percent / diethyl ether; tetrahydrofuran / -78 - 20 °C

7.1: 91 percent / NHMDS / 10 h / 20 °C

8.1: 89 percent / n-Bu₃SnH; AIBN / toluene / 2 h / Heating

9.1: 100 percent / aq. HCl / tetrahydrofuran / 11 h / 50 °C

10.1: 93 percent / Dess-Martin periodinane / CH₂Cl₂ / 1 h / 20 °C

11.1: 94 percent / t-BuOK / benzene / 2 h / 0 - 20 °C

12.1: 71 percent / SOCl₂; pyridine / CH₂Cl₂ / 2 h / 0 - 20 °C

With pyridine; hydrogenchloride; thionyl chloride; 2,2'-azobis(isobutyronitrile); camphor-10-sulfonic acid; potassium tert-butylate; hydrogen; iodine; tert.-butyl lithium; tri-n-butyl-tin hydride; sodium hexamethyldisilazane; diisobutylaluminium hydride; Dess-Martin periodane; N-ethyl-N,N-diisopropylamine; triphenylphosphine; nickel; In tetrahydrofuran; diethyl ether; hexane; dichloromethane; toluene; benzene; 10.1: Dess-Martin oxidation;

DOI:10.1021/ol048010i

Reference yield:

(S)-7-methyl-7-phenylsulfanylmethyl-1,4-dioxa-spiro[4.4]nonane (824940-78-5) → (+)-(3aS,5aR,6S,9bR)-6-(4-methoxybenzyloxy)-3,3a,4,5,5a,6,7,8-octahydro-3a,5a-dimethyl-2H-cyclopenta[a]naphthalen-1(9bH)-one (824940-71-8)

Guidance literature:

Multi-step reaction with 9 steps

1.1: 100 percent / m-CPBA / CH₂Cl₂ / 1 h / -40 °C

2.1: 87 percent / TFAA; TEA / 3 h / 20 °C

3.1: t-BuLi / diethyl ether; tetrahydrofuran / -78 °C

3.2: 79 percent / diethyl ether; tetrahydrofuran / -78 - 20 °C

4.1: 91 percent / NHMDS / 10 h / 20 °C

5.1: 89 percent / n-Bu₃SnH; AIBN / toluene / 2 h / Heating

6.1: 100 percent / aq. HCl / tetrahydrofuran / 11 h / 50 °C

7.1: 93 percent / Dess-Martin periodinane / CH₂Cl₂ / 1 h / 20 °C

8.1: 94 percent / t-BuOK / benzene / 2 h / 0 - 20 °C

9.1: 71 percent / SOCl₂; pyridine / CH₂Cl₂ / 2 h / 0 - 20 °C

With pyridine; hydrogenchloride; thionyl chloride; 2,2'-azobis(isobutyronitrile); TEA; potassium tert-butylate; tert.-butyl lithium; tri-n-butyl-tin hydride; sodium hexamethyldisilazane; Dess-Martin periodane; 3-chloro-benzenecarboperoxoic acid; trifluoroacetic anhydride; In tetrahydrofuran; diethyl ether; dichloromethane; toluene; benzene; 7.1: Dess-Martin oxidation;

DOI:10.1021/ol048010i

upstream raw materials:

(+)-(3aS,5aS,6S,9aR,9bR)-6-(4-methoxybenzyloxy)-decahydro-9a-hydroxy-3a,5a-dimethyl-2H-cyclopenta[a]naphthalen-1(9bH)-one

(S)-7-methyl-7-phenylsulfanylmethyl-1,4-dioxa-spiro[4.4]nonane

(S)-7-benzenesilfinylmethyl-7-methyl-1,4-dioxa-spiro[4.4]nonane

(2R,4aR,5S,8aS)-hexahydro-2-(4-methoxyphenyl)-4a-methyl-4H-benzo[d][1,3]dioxin-5-ol

Downstream raw materials:

(+)-allocyathin B₂