(1S,4aS,6aS,12aR,12bR)-9-(3,4-Dimethoxy-phenyl)-1,4a,12a-trihydroxy-4,4,6a,12b-tetramethyl-1,3,4,4a,5,6,6a,12,12a,12b-decahydro-2H-7,10-dioxa-benzo[a]anthracen-11-one

Base Information

Chemical Name:(1S,4aS,6aS,12aR,12bR)-9-(3,4-Dimethoxy-phenyl)-1,4a,12a-trihydroxy-4,4,6a,12b-tetramethyl-1,3,4,4a,5,6,6a,12,12a,12b-decahydro-2H-7,10-dioxa-benzo[a]anthracen-11-one
CAS No.:489413-14-1
Molecular Formula:C₂₈H₃₆O₈
Molecular Weight:500.589
Hs Code.:

(1S,4aS,6aS,12aR,12bR)-9-(3,4-Dimethoxy-phenyl)-1,4a,12a-trihydroxy-4,4,6a,12b-tetramethyl-1,3,4,4a,5,6,6a,12,12a,12b-decahydro-2H-7,10-dioxa-benzo[a]anthracen-11-one

Synonyms:(1S,4aS,6aS,12aR,12bR)-9-(3,4-Dimethoxy-phenyl)-1,4a,12a-trihydroxy-4,4,6a,12b-tetramethyl-1,3,4,4a,5,6,6a,12,12a,12b-decahydro-2H-7,10-dioxa-benzo[a]anthracen-11-one

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Chemical Property of (1S,4aS,6aS,12aR,12bR)-9-(3,4-Dimethoxy-phenyl)-1,4a,12a-trihydroxy-4,4,6a,12b-tetramethyl-1,3,4,4a,5,6,6a,12,12a,12b-decahydro-2H-7,10-dioxa-benzo[a]anthracen-11-one

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Technology Process of (1S,4aS,6aS,12aR,12bR)-9-(3,4-Dimethoxy-phenyl)-1,4a,12a-trihydroxy-4,4,6a,12b-tetramethyl-1,3,4,4a,5,6,6a,12,12a,12b-decahydro-2H-7,10-dioxa-benzo[a]anthracen-11-one

There total 11 articles about (1S,4aS,6aS,12aR,12bR)-9-(3,4-Dimethoxy-phenyl)-1,4a,12a-trihydroxy-4,4,6a,12b-tetramethyl-1,3,4,4a,5,6,6a,12,12a,12b-decahydro-2H-7,10-dioxa-benzo[a]anthracen-11-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: 93.0%

: 489413-12-9
Acetic acid (1S,4aS,6aS,12aR,12bR)-9-(3,4-dimethoxy-phenyl)-4a,12a-dihydroxy-4,4,6a,12b-tetramethyl-11-oxo-1,3,4,4a,5,6,6a,12,12a,12b-decahydro-2H,11H-7,10-dioxa-benzo[a]anthracen-1-yl ester

: 489413-14-1
(1S,4aS,6aS,12aR,12bR)-9-(3,4-Dimethoxy-phenyl)-1,4a,12a-trihydroxy-4,4,6a,12b-tetramethyl-1,3,4,4a,5,6,6a,12,12a,12b-decahydro-2H-7,10-dioxa-benzo[a]anthracen-11-one

Guidance literature:: With potassium carbonate; In methanol; at 20 ℃; for 2h;
DOI:10.1016/S0040-4039(02)02094-4

Reference yield:

: 123286-37-3
(R)-2,4,4-trimethyl-3-vinyl-2-cyclohexene-1-ol

: 489413-14-1
(1S,4aS,6aS,12aR,12bR)-9-(3,4-Dimethoxy-phenyl)-1,4a,12a-trihydroxy-4,4,6a,12b-tetramethyl-1,3,4,4a,5,6,6a,12,12a,12b-decahydro-2H-7,10-dioxa-benzo[a]anthracen-11-one

Guidance literature:: Multi-step reaction with 11 steps

1: DCC; DMAP / CH₂Cl₂ / 0 - 20 °C

2: decane / 23 h / Heating

3: 64 percent / m-CPBA / CH₂Cl₂ / 48 h / 0 °C

4: 90 percent / AlCl₃; LAH / tetrahydrofuran / 2 h / -78 - 20 °C

5: 73 percent / 5 mol percent TPAP; NMO; molecular sieves / CH₂Cl₂ / 20 °C

6: 54 percent / L-proline / tetrahydrofuran / 65 °C

7: 92 percent / 5 mol percent TPAP; NMO / CH₂Cl₂ / 3 h

8: 94 percent / NMe₄BH(OAc)3 / acetic acid / 0.5 h / 20 °C

9: 21 percent / CH₂Cl₂ / 20 °C / pH 7

10: 83 percent / Et₃SiH; TFA / CH₂Cl₂ / 4 h / 20 °C

11: 93 percent / K₂CO₃ / methanol / 2 h / 20 °C

With triethylsilane; dmap; lithium aluminium tetrahydride; aluminium trichloride; N-methyl-2-indolinone; molecular sieve; tetrapropylammonium perruthennate; potassium carbonate; 3-chloro-benzenecarboperoxoic acid; dicyclohexyl-carbodiimide; trifluoroacetic acid; L-proline; tetramethylammonium triacetoxyborohydride; In tetrahydrofuran; methanol; decane; dichloromethane; acetic acid; 2: Diels-Alder cycloaddition / 5: Ley's oxidation / 7: Ley's oxidation;
DOI:10.1016/S0040-4039(02)02094-4

Reference yield:

: But-2-ynoic acid (R)-2,4,4-trimethyl-3-vinyl-cyclohex-2-enyl ester

: 489413-14-1
(1S,4aS,6aS,12aR,12bR)-9-(3,4-Dimethoxy-phenyl)-1,4a,12a-trihydroxy-4,4,6a,12b-tetramethyl-1,3,4,4a,5,6,6a,12,12a,12b-decahydro-2H-7,10-dioxa-benzo[a]anthracen-11-one

Guidance literature:: Multi-step reaction with 10 steps

1: decane / 23 h / Heating

2: 64 percent / m-CPBA / CH₂Cl₂ / 48 h / 0 °C

3: 90 percent / AlCl₃; LAH / tetrahydrofuran / 2 h / -78 - 20 °C

4: 73 percent / 5 mol percent TPAP; NMO; molecular sieves / CH₂Cl₂ / 20 °C

5: 54 percent / L-proline / tetrahydrofuran / 65 °C

6: 92 percent / 5 mol percent TPAP; NMO / CH₂Cl₂ / 3 h

7: 94 percent / NMe₄BH(OAc)3 / acetic acid / 0.5 h / 20 °C

8: 21 percent / CH₂Cl₂ / 20 °C / pH 7

9: 83 percent / Et₃SiH; TFA / CH₂Cl₂ / 4 h / 20 °C

10: 93 percent / K₂CO₃ / methanol / 2 h / 20 °C

With triethylsilane; lithium aluminium tetrahydride; aluminium trichloride; N-methyl-2-indolinone; molecular sieve; tetrapropylammonium perruthennate; potassium carbonate; 3-chloro-benzenecarboperoxoic acid; trifluoroacetic acid; L-proline; tetramethylammonium triacetoxyborohydride; In tetrahydrofuran; methanol; decane; dichloromethane; acetic acid; 1: Diels-Alder cycloaddition / 4: Ley's oxidation / 6: Ley's oxidation;
DOI:10.1016/S0040-4039(02)02094-4