(4aR,4bS,6aR,8R,10aR,10bR,12aR)-1,4,4a,4b,5,6,7,8,9,10,10a,10b,11,12,12a-hexadecahydro-2-methoxy-1,1,10a-trimethyl-4,11-dioxo-8-(phenylmethoxy)chrysene-4a-carboxaldehyde

Base Information

• Chemical Name: (4aR,4bS,6aR,8R,10aR,10bR,12aR)-1,4,4a,4b,5,6,7,8,9,10,10a,10b,11,12,12a-hexadecahydro-2-methoxy-1,1,10a-trimethyl-4,11-dioxo-8-(phenylmethoxy)chrysene-4a-carboxaldehyde
• CAS No.: 652153-11-2
• Molecular Formula: C₃₀H₃₈O₅
• Molecular Weight: 478.629
• Mol file: 652153-11-2.mol

Synonyms:(4aR,4bS,6aR,8R,10aR,10bR,12aR)-1,4,4a,4b,5,6,7,8,9,10,10a,10b,11,12,12a-hexadecahydro-2-methoxy-1,1,10a-trimethyl-4,11-dioxo-8-(phenylmethoxy)chrysene-4a-carboxaldehyde

Chemical Property of (4aR,4bS,6aR,8R,10aR,10bR,12aR)-1,4,4a,4b,5,6,7,8,9,10,10a,10b,11,12,12a-hexadecahydro-2-methoxy-1,1,10a-trimethyl-4,11-dioxo-8-(phenylmethoxy)chrysene-4a-carboxaldehyde

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (4aR,4bS,6aR,8R,10aR,10bR,12aR)-1,4,4a,4b,5,6,7,8,9,10,10a,10b,11,12,12a-hexadecahydro-2-methoxy-1,1,10a-trimethyl-4,11-dioxo-8-(phenylmethoxy)chrysene-4a-carboxaldehyde

There total 14 articles about (4aR,4bS,6aR,8R,10aR,10bR,12aR)-1,4,4a,4b,5,6,7,8,9,10,10a,10b,11,12,12a-hexadecahydro-2-methoxy-1,1,10a-trimethyl-4,11-dioxo-8-(phenylmethoxy)chrysene-4a-carboxaldehyde 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: 70.0%

4-methoxy-3,3-dimethyl-6-oxocyclohexa-1,4-diene-1-carboxaldehyde (652153-12-3) + (4aR,6R,8aS)-3,4,4a,5,6,7,8,8a-octahydro-8a-methoxy-β-oxo-6-(phenylmethoxy)naphthalene-1-propanoic acid prop-2-enyl ester (652153-13-4) → (4aR,4bS,6aR,8R,10aR,10bR,12aR)-1,4,4a,4b,5,6,7,8,9,10,10a,10b,11,12,12a-hexadecahydro-2-methoxy-1,1,10a-trimethyl-4,11-dioxo-8-(phenylmethoxy)chrysene-4a-carboxaldehyde (652153-11-2)

Guidance literature:

4-methoxy-3,3-dimethyl-6-oxocyclohexa-1,4-diene-1-carboxaldehyde; (4aR,6R,8aS)-3,4,4a,5,6,7,8,8a-octahydro-8a-methoxy-β-oxo-6-(phenylmethoxy)naphthalene-1-propanoic acid prop-2-enyl ester; With caesium carbonate; In ethyl acetate; at 20 ℃; for 96h;

With morpholine; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In tetrahydrofuran; at 20 ℃; for 1h;

DOI:10.1002/hlca.200390315

Reference yield:

(4aR,6R,8aR)-6-Benzyloxy-8a-methyl-octahydro-naphthalen-1-one → (4aR,4bS,6aR,8R,10aR,10bR,12aR)-1,4,4a,4b,5,6,7,8,9,10,10a,10b,11,12,12a-hexadecahydro-2-methoxy-1,1,10a-trimethyl-4,11-dioxo-8-(phenylmethoxy)chrysene-4a-carboxaldehyde (652153-11-2)

Guidance literature:

Multi-step reaction with 8 steps

1.1: 90 percent / Proton Sponge(R) / CH₂Cl₂ / 16 h / 20 °C

2.1: 83 percent / K₂CO₃; LiCl; 1-methylpyrrolidin-2-one / dichlorobis(triphenylphosphine)palladium / 24 h / 130 °C / 10343 Torr

3.1: 86 percent / Dibal-H / CH₂Cl₂ / -78 °C

4.1: 89 percent / Dess-Martin periodinane / CH₂Cl₂ / 0.75 h / 20 °C

5.1: Zn; I₂ / diethyl ether / 2 h / 20 °C

5.2: 87 percent / diethyl ether / 3 h / 20 °C

6.1: 92 percent / Dess-Martin periodianne / CH₂Cl₂ / 0.75 h / 20 °C

7.1: 82 percent / DMAP / toluene / 16 h / Heating

8.1: Cs₂CO₃ / ethyl acetate / 96 h / 20 °C

8.2: 70 percent / morpholine; [Pd(PPh₃)4] / tetrahydrofuran / 1 h / 20 °C

With 1-methyl-pyrrolidin-2-one; dmap; iodine; N,N,N',N'-tetramethyl-1,8-diaminonaphthalene; diisobutylaluminium hydride; potassium carbonate; caesium carbonate; Dess-Martin periodane; lithium chloride; zinc; bis-triphenylphosphine-palladium(II) chloride; In diethyl ether; dichloromethane; ethyl acetate; toluene;

DOI:10.1002/hlca.200390315

Reference yield:

(4aR,6R,8aS)-3,4,4a,5,6,7,8,8a-octahydro-8a-methyl-6-(phenylmethoxy)naphthalen-1-ol trifluoronethanesulfonate (652153-15-6) → (4aR,4bS,6aR,8R,10aR,10bR,12aR)-1,4,4a,4b,5,6,7,8,9,10,10a,10b,11,12,12a-hexadecahydro-2-methoxy-1,1,10a-trimethyl-4,11-dioxo-8-(phenylmethoxy)chrysene-4a-carboxaldehyde (652153-11-2)

Guidance literature:

Multi-step reaction with 7 steps

1.1: 83 percent / K₂CO₃; LiCl; 1-methylpyrrolidin-2-one / dichlorobis(triphenylphosphine)palladium / 24 h / 130 °C / 10343 Torr

2.1: 86 percent / Dibal-H / CH₂Cl₂ / -78 °C

3.1: 89 percent / Dess-Martin periodinane / CH₂Cl₂ / 0.75 h / 20 °C

4.1: Zn; I₂ / diethyl ether / 2 h / 20 °C

4.2: 87 percent / diethyl ether / 3 h / 20 °C

5.1: 92 percent / Dess-Martin periodianne / CH₂Cl₂ / 0.75 h / 20 °C

6.1: 82 percent / DMAP / toluene / 16 h / Heating

7.1: Cs₂CO₃ / ethyl acetate / 96 h / 20 °C

7.2: 70 percent / morpholine; [Pd(PPh₃)4] / tetrahydrofuran / 1 h / 20 °C

With 1-methyl-pyrrolidin-2-one; dmap; iodine; diisobutylaluminium hydride; potassium carbonate; caesium carbonate; Dess-Martin periodane; lithium chloride; zinc; bis-triphenylphosphine-palladium(II) chloride; In diethyl ether; dichloromethane; ethyl acetate; toluene;

DOI:10.1002/hlca.200390315

upstream raw materials:

4-methoxy-3,3-dimethyl-6-oxocyclohexa-1,4-diene-1-carboxaldehyde

(4aR,6R,8aS)-3,4,4a,5,6,7,8,8a-octahydro-8a-methoxy-β-oxo-6-(phenylmethoxy)naphthalene-1-propanoic acid prop-2-enyl ester

O-benzyl 2,2,2-trichloroacetimidate

(4aR,6R,8aR)-6-hydroxy-8a-methyloctahydronaphthalen-1(2H)-one

Downstream raw materials:

Thiocarbonic acid O-((4aR,4bS,6aR,8R,10aR,10bR,12aR)-8-benzyloxy-2-methoxy-1,1,10a-trimethyl-4,11-dioxo-1,4b,5,6,6a,7,8,9,10,10a,10b,11,12,12a-tetradecahydro-4H-chrysen-4a-ylmethyl) ester O-phenyl ester

(4aR,4bS,6aR,8R,10aR,10bR,12aR)-4b,5,6,6a,7,8,9,10,10a,10b,12,12a-dodecahydro-2-methoxy-1,1,4a,10a-tetramethyl-8-(phenylmethoxy)chrysene-4,11(1H,4aH)-dione

(4aR,4bS,6aR,8R,10aR,10bR,12aR)-4b,5,6,6a,7,8,9,10,10a,10b,12,12a-dodecahydro-4a-(hydroxymethyl)-2-methoxy-1,1,10a-trimethyl-8-(phenylmethoxy)chrysene-4,11(1H,4aH)-dione