(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

Base Information

Chemical Name:(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
CAS No.:769126-98-9
Molecular Formula:C₂₈H₃₄O₈
Molecular Weight:498.573
Hs Code.:

(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

Synonyms:(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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Chemical Property of (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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Technology Process of (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

There total 13 articles about (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 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%

: 769122-52-3
(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

: 769126-98-9
(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

Guidance literature:: With tetrapropylammonium perruthennate; 4-methylmorpholine N-oxide; In dichloromethane; at 20 ℃; for 0.333333h;
DOI:10.1016/j.tet.2004.06.059

Reference yield:

: 85679-49-8
2,4,4-trimethyl-3-vinyl-cyclohex-2-enone

: 769126-98-9
(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

Guidance literature:: Multi-step reaction with 13 steps

1.1: KOH; H₂ / RuCl₂[(R)-binap,(S,S)-DPEN] / propan-2-ol / 24 h / 20 °C / 6080 Torr

1.2: 11.6 g / DMAP / pyridine / 1.5 h / 20 °C

2.1: 99 percent / K₂CO₃ / methanol; CH₂Cl₂ / 2.5 h / 20 °C

3.1: 85 percent / DCC; DMAP / CH₂Cl₂ / 5 h / 20 °C

4.1: 35 percent / decane / 14 h / 180 °C

5.1: 77 percent / m-CPBA / CH₂Cl₂ / 24 h / 20 °C

6.1: 98 percent / LiAlH₄; AlCl₃ / tetrahydrofuran / 1 h / 0 °C

7.1: 73 percent / 4-methylmorpholine N-oxide; tetrapropylammonium perruthenate / CH₂Cl₂ / 1.5 h / 20 °C

8.1: 61 percent / L-proline / tetrahydrofuran / 14 h / 65 °C

9.1: 100 percent / 4-methylmorpholine N-oxide; tetrapropylammonium perruthenate / CH₂Cl₂ / 1.5 h / 20 °C

10.1: 71 percent / NaBH(OAc)3 / tetrahydrofuran / 15 h / 20 °C

11.1: 41 percent / aq. phosphate buffer; acetic acid / 120 h / 20 °C

12.1: Et₃SiH; TFA / 1,2-dichloro-ethane / 18 h / 50 °C

12.2: 82 percent / K₂CO₃ / methanol / 4 h / 20 °C

13.1: 100 percent / 4-methylmorpholine N-oxide; tetrapropylammonium perruthenate / CH₂Cl₂ / 0.33 h / 20 °C

With triethylsilane; dmap; potassium hydroxide; lithium aluminium tetrahydride; aluminium trichloride; tetrapropylammonium perruthennate; hydrogen; sodium tris(acetoxy)borohydride; potassium carbonate; 4-methylmorpholine N-oxide; 3-chloro-benzenecarboperoxoic acid; dicyclohexyl-carbodiimide; trifluoroacetic acid; L-proline; [RuCl₂(R-BINAP)(S,S-DPEN)]; In tetrahydrofuran; methanol; phosphate buffer; decane; dichloromethane; acetic acid; 1,2-dichloro-ethane; isopropyl alcohol; 4.1: Diels-Akder reaction;
DOI:10.1016/j.tet.2004.06.059

Reference yield:

: 347393-59-3
(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

: 769126-98-9
(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

Guidance literature:: Multi-step reaction with 8 steps

1.1: 98 percent / LiAlH₄; AlCl₃ / tetrahydrofuran / 1 h / 0 °C

2.1: 73 percent / 4-methylmorpholine N-oxide; tetrapropylammonium perruthenate / CH₂Cl₂ / 1.5 h / 20 °C

3.1: 61 percent / L-proline / tetrahydrofuran / 14 h / 65 °C

4.1: 100 percent / 4-methylmorpholine N-oxide; tetrapropylammonium perruthenate / CH₂Cl₂ / 1.5 h / 20 °C

5.1: 71 percent / NaBH(OAc)3 / tetrahydrofuran / 15 h / 20 °C

6.1: 41 percent / aq. phosphate buffer; acetic acid / 120 h / 20 °C

7.1: Et₃SiH; TFA / 1,2-dichloro-ethane / 18 h / 50 °C

7.2: 82 percent / K₂CO₃ / methanol / 4 h / 20 °C

8.1: 100 percent / 4-methylmorpholine N-oxide; tetrapropylammonium perruthenate / CH₂Cl₂ / 0.33 h / 20 °C

With triethylsilane; lithium aluminium tetrahydride; aluminium trichloride; tetrapropylammonium perruthennate; sodium tris(acetoxy)borohydride; 4-methylmorpholine N-oxide; trifluoroacetic acid; L-proline; In tetrahydrofuran; phosphate buffer; dichloromethane; acetic acid; 1,2-dichloro-ethane;
DOI:10.1016/j.tet.2004.06.059