(4aR,6aR,12bS)-3,4,4a,5,6,6a,12b-heptahydro-4a-hydroxy-4,4,6a,12b-tetramethyl-9-(3',4'-dimethoxyphenyl)-2H,11H-naphtho[2,1-b]pyrano[3,4-e]pyran-1,11(3H)-dione

Base Information

• Chemical Name: (4aR,6aR,12bS)-3,4,4a,5,6,6a,12b-heptahydro-4a-hydroxy-4,4,6a,12b-tetramethyl-9-(3',4'-dimethoxyphenyl)-2H,11H-naphtho[2,1-b]pyrano[3,4-e]pyran-1,11(3H)-dione
• CAS No.: 346688-16-2
• Molecular Formula: C₂₈H₃₂O₇
• Molecular Weight: 480.558

Synonyms:(4aR,6aR,12bS)-3,4,4a,5,6,6a,12b-heptahydro-4a-hydroxy-4,4,6a,12b-tetramethyl-9-(3',4'-dimethoxyphenyl)-2H,11H-naphtho[2,1-b]pyrano[3,4-e]pyran-1,11(3H)-dione

Chemical Property of (4aR,6aR,12bS)-3,4,4a,5,6,6a,12b-heptahydro-4a-hydroxy-4,4,6a,12b-tetramethyl-9-(3',4'-dimethoxyphenyl)-2H,11H-naphtho[2,1-b]pyrano[3,4-e]pyran-1,11(3H)-dione

Chemical Property:

Purity/Quality:

Safty Information:

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Technology Process of (4aR,6aR,12bS)-3,4,4a,5,6,6a,12b-heptahydro-4a-hydroxy-4,4,6a,12b-tetramethyl-9-(3',4'-dimethoxyphenyl)-2H,11H-naphtho[2,1-b]pyrano[3,4-e]pyran-1,11(3H)-dione

There total 8 articles about (4aR,6aR,12bS)-3,4,4a,5,6,6a,12b-heptahydro-4a-hydroxy-4,4,6a,12b-tetramethyl-9-(3',4'-dimethoxyphenyl)-2H,11H-naphtho[2,1-b]pyrano[3,4-e]pyran-1,11(3H)-dione 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: 100.0%

(1S,4aR,6aR,12bS)-1,3,4,4a,5,6,6a,12b-octahydro-1,4a-dihydroxy-4,4,6a,12b-tetramethyl-9-(3',4'-dimethoxyphenyl)-2H,11H-naphtho[2,1-b]pyrano[3,4-e]pyran-11-one (346688-14-0) → (4aR,6aR,12bS)-3,4,4a,5,6,6a,12b-heptahydro-4a-hydroxy-4,4,6a,12b-tetramethyl-9-(3',4'-dimethoxyphenyl)-2H,11H-naphtho[2,1-b]pyrano[3,4-e]pyran-1,11(3H)-dione (346688-16-2)

Guidance literature:

With tetrapropylammonium perruthennate; 4-methylmorpholine N-oxide; In dichloromethane; at 20 ℃; for 1.5h;

DOI:10.1016/j.tet.2004.06.059

Reference yield:

(1aS,5aS,8aR,8bR)-1a,2,5a,7,8,8b-hexahydro-3,8,8,8b-tetramethyl-4H,6H-oxireno[4a,5]naphtho[1,8-bc]furan-4-one (347393-59-3) → (4aR,6aR,12bS)-3,4,4a,5,6,6a,12b-heptahydro-4a-hydroxy-4,4,6a,12b-tetramethyl-9-(3',4'-dimethoxyphenyl)-2H,11H-naphtho[2,1-b]pyrano[3,4-e]pyran-1,11(3H)-dione (346688-16-2)

Guidance literature:

Multi-step reaction with 4 steps

1: 98 percent / LiAlH₄; AlCl₃ / tetrahydrofuran / 1 h / 0 °C

2: 73 percent / 4-methylmorpholine N-oxide; tetrapropylammonium perruthenate / CH₂Cl₂ / 1.5 h / 20 °C

3: 61 percent / L-proline / tetrahydrofuran / 14 h / 65 °C

4: 100 percent / 4-methylmorpholine N-oxide; tetrapropylammonium perruthenate / CH₂Cl₂ / 1.5 h / 20 °C

With lithium aluminium tetrahydride; aluminium trichloride; tetrapropylammonium perruthennate; 4-methylmorpholine N-oxide; L-proline; In tetrahydrofuran; dichloromethane;

DOI:10.1016/j.tet.2004.06.059

Reference yield:

(4aR,8S,8aS)-1-formyl-3,4,4a,5,6,7,8,8a-octahydro-4a,8-dihydroxy-2,5,5,8a-tetramethylnaphthalene (346688-12-8) → (4aR,6aR,12bS)-3,4,4a,5,6,6a,12b-heptahydro-4a-hydroxy-4,4,6a,12b-tetramethyl-9-(3',4'-dimethoxyphenyl)-2H,11H-naphtho[2,1-b]pyrano[3,4-e]pyran-1,11(3H)-dione (346688-16-2)

Guidance literature:

Multi-step reaction with 2 steps

1: 61 percent / L-proline / tetrahydrofuran / 14 h / 65 °C

2: 100 percent / 4-methylmorpholine N-oxide; tetrapropylammonium perruthenate / CH₂Cl₂ / 1.5 h / 20 °C

With tetrapropylammonium perruthennate; 4-methylmorpholine N-oxide; L-proline; In tetrahydrofuran; dichloromethane;

DOI:10.1016/j.tet.2004.06.059

upstream raw materials:

(1S,4aR,6aR,12bS)-1,3,4,4a,5,6,6a,12b-octahydro-1,4a-dihydroxy-4,4,6a,12b-tetramethyl-9-(3',4'-dimethoxyphenyl)-2H,11H-naphtho[2,1-b]pyrano[3,4-e]pyran-11-one

(1aS,5aS,8aR,8bR)-1a,2,5a,7,8,8b-hexahydro-3,8,8,8b-tetramethyl-4H,6H-oxireno[4a,5]naphtho[1,8-bc]furan-4-one

(4aR,8S,8aS)-1-formyl-3,4,4a,5,6,7,8,8a-octahydro-4a,8-dihydroxy-2,5,5,8a-tetramethylnaphthalene

(1S)-3'-ethenyl-2',4',4'-trimethyl-2'-cyclohexenyl 3,5-dinitrobenzoate

Downstream raw materials:

(1R,4aR,6aR,12bS)-1,3,4,4a,5,6,6a,12b-octahydro-1,4a-dihydroxy-4,4,6a,12b-tetramethyl-9-(3',4'-dimethoxyphenyl)-2H,11H-naphtho[2,1-b]pyrano[3,4-e]pyran-11-one

(1R,4aR,6aR,12R,12aR,12bS)-1-acetoxy-1,3,4,4a,5,6,6a,12,12a,12b-decahydro-4a,12,12a-trihydroxy-4,4,6a,12b-tetramethyl-9-(3',4'-dimethoxyphenyl)-2H,11H-naphtho[2,1-b]pyrano[3,4-e]pyran-11-one

(1R,4aR,6aR,12aR,12bS)-1,3,4,4a,5,6,6a,12,12a,12b-decahydro-1,4a,12a-trihydroxy-4,4,6a,12b-tetramethyl-9-(3',4'-dimethoxyphenyl)-2H,11H-naphtho[2,1-b]pyrano[3,4-e]pyran-11-one

(4aR,6aR,12aR,12bS)-3,4,4a,5,6,6a,12,12a,12b-nonahydro-4a,12a-dihydroxy-4,4,6a,12b-tetramethyl-9-(3',4'-dimethoxyphenyl)-2H,11H-naphtho[2,1-b]pyrano[3,4-e]pyran-1,11(3H)-dione

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