(4aS,9aS)-9a-(3,4-dimethyl-3-pentenyl)-6-methoxycarbonyl-3,3-dimethyl-9-(p-toluenesulfonyl)-9-aza-2,4-dioxa-1,2,3,4,4a,10,9,9a-octahydroanthracene

Base Information

Chemical Name:(4aS,9aS)-9a-(3,4-dimethyl-3-pentenyl)-6-methoxycarbonyl-3,3-dimethyl-9-(p-toluenesulfonyl)-9-aza-2,4-dioxa-1,2,3,4,4a,10,9,9a-octahydroanthracene
CAS No.:181369-05-1
Molecular Formula:C₂₉H₃₇NO₆S
Molecular Weight:527.682
Hs Code.:

(4aS,9aS)-9a-(3,4-dimethyl-3-pentenyl)-6-methoxycarbonyl-3,3-dimethyl-9-(p-toluenesulfonyl)-9-aza-2,4-dioxa-1,2,3,4,4a,10,9,9a-octahydroanthracene

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Chemical Property of (4aS,9aS)-9a-(3,4-dimethyl-3-pentenyl)-6-methoxycarbonyl-3,3-dimethyl-9-(p-toluenesulfonyl)-9-aza-2,4-dioxa-1,2,3,4,4a,10,9,9a-octahydroanthracene

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Technology Process of (4aS,9aS)-9a-(3,4-dimethyl-3-pentenyl)-6-methoxycarbonyl-3,3-dimethyl-9-(p-toluenesulfonyl)-9-aza-2,4-dioxa-1,2,3,4,4a,10,9,9a-octahydroanthracene

There total 22 articles about (4aS,9aS)-9a-(3,4-dimethyl-3-pentenyl)-6-methoxycarbonyl-3,3-dimethyl-9-(p-toluenesulfonyl)-9-aza-2,4-dioxa-1,2,3,4,4a,10,9,9a-octahydroanthracene 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:

: 59816-84-1
ethyl 4-amino-3-(2-propenyl)benzoate

: 181369-05-1
(4aS,9aS)-9a-(3,4-dimethyl-3-pentenyl)-6-methoxycarbonyl-3,3-dimethyl-9-(p-toluenesulfonyl)-9-aza-2,4-dioxa-1,2,3,4,4a,10,9,9a-octahydroanthracene

Guidance literature:: Multi-step reaction with 19 steps

1: 100 percent / pyridine / CH₂Cl₂ / 17 h / Ambient temperature

2: 95 percent / LiAlH₄ / tetrahydrofuran / 2 h / Ambient temperature

3: 82 percent / imidazole / dimethylformamide / 85 h / 60 °C

4: 1.) aq. OsO₄, 2.) NaIO₄ / 1.) THF, RT, 30 min, 2.) THF, RT, 2 h

5: 87 percent / CH₂Cl₂ / 52 h / Ambient temperature

6: 92 percent / DIBALH / toluene / 0.5 h / -15 °C

7: Et₃N / CH₂Cl₂ / 0.5 h / 0 °C

8: Et₃N / CH₂Cl₂ / 0.5 h / 0 °C

9: aq. citric acid*H₂O / diethyl ether; methanol / 0.83 h / Ambient temperature

10: L-(+)-diethyl tartrate, Ti(O-Pr)4, tert-butyl hydroperoxide / CH₂Cl₂ / 1.5 h / -20 °C

11: 95 percent / Et₃N / CH₂Cl₂ / 0.5 h / 0 °C

12: 87 percent / Zn, NaI / dimethylformamide / 0.25 h / 100 °C

13: 98 percent / DIBALH / toluene; hexane / 0.5 h / -15 °C

14: 96 percent / vanadyl acetylacetonate, tert-butyl hydroperoxide / CH₂Cl₂ / 2.5 h / 0 °C

15: 67 percent / TFA / toluene / 6 h / Ambient temperature

16: 92 percent / camphorsulfonic acid / acetone / 3 h / Ambient temperature

17: 99 percent / n-Bu₄NF / tetrahydrofuran / 15 h / Ambient temperature

18: pyridinium dichromate / CH₂Cl₂ / 4 h / Ambient temperature

19: MnO₂, KCN, AcOH / benzene / 13 h / Ambient temperature

With pyridine; 1H-imidazole; tert.-butylhydroperoxide; potassium cyanide; manganese(IV) oxide; sodium periodate; osmium(VIII) oxide; lithium aluminium tetrahydride; dipyridinium dichromate; titanium tetra-n-propoxide; diethyl (2R,3R)-tartrate; vanadyl acetylacetonate; camphor-10-sulfonic acid; tetrabutyl ammonium fluoride; diisobutylaluminium hydride; acetic acid; triethylamine; trifluoroacetic acid; citric acid; sodium iodide; zinc; In tetrahydrofuran; methanol; diethyl ether; hexane; dichloromethane; N,N-dimethyl-formamide; acetone; toluene; benzene;
DOI:10.1016/0040-4020(96)00608-4

Reference yield:

: 119139-47-8
methyl 5,6-dimethyl-2-triphenylphosphoranylidene-5-heptenoate

: 181369-05-1
(4aS,9aS)-9a-(3,4-dimethyl-3-pentenyl)-6-methoxycarbonyl-3,3-dimethyl-9-(p-toluenesulfonyl)-9-aza-2,4-dioxa-1,2,3,4,4a,10,9,9a-octahydroanthracene

Guidance literature:: Multi-step reaction with 15 steps

1: 87 percent / CH₂Cl₂ / 52 h / Ambient temperature

2: 92 percent / DIBALH / toluene / 0.5 h / -15 °C

3: Et₃N / CH₂Cl₂ / 0.5 h / 0 °C

4: Et₃N / CH₂Cl₂ / 0.5 h / 0 °C

5: aq. citric acid*H₂O / diethyl ether; methanol / 0.83 h / Ambient temperature

6: L-(+)-diethyl tartrate, Ti(O-Pr)4, tert-butyl hydroperoxide / CH₂Cl₂ / 1.5 h / -20 °C

7: 95 percent / Et₃N / CH₂Cl₂ / 0.5 h / 0 °C

8: 87 percent / Zn, NaI / dimethylformamide / 0.25 h / 100 °C

9: 98 percent / DIBALH / toluene; hexane / 0.5 h / -15 °C

10: 96 percent / vanadyl acetylacetonate, tert-butyl hydroperoxide / CH₂Cl₂ / 2.5 h / 0 °C

11: 67 percent / TFA / toluene / 6 h / Ambient temperature

12: 92 percent / camphorsulfonic acid / acetone / 3 h / Ambient temperature

13: 99 percent / n-Bu₄NF / tetrahydrofuran / 15 h / Ambient temperature

14: pyridinium dichromate / CH₂Cl₂ / 4 h / Ambient temperature

15: MnO₂, KCN, AcOH / benzene / 13 h / Ambient temperature

With tert.-butylhydroperoxide; potassium cyanide; manganese(IV) oxide; dipyridinium dichromate; titanium tetra-n-propoxide; diethyl (2R,3R)-tartrate; vanadyl acetylacetonate; camphor-10-sulfonic acid; tetrabutyl ammonium fluoride; diisobutylaluminium hydride; acetic acid; triethylamine; trifluoroacetic acid; citric acid; sodium iodide; zinc; In tetrahydrofuran; methanol; diethyl ether; hexane; dichloromethane; N,N-dimethyl-formamide; acetone; toluene; benzene;
DOI:10.1016/0040-4020(96)00608-4

Reference yield:

: 119139-40-1
5-(tert-butyldiphenylsilyl)oxymethyl-1-(p-toluenesulfonyl)-2-indolinole

: 181369-05-1
(4aS,9aS)-9a-(3,4-dimethyl-3-pentenyl)-6-methoxycarbonyl-3,3-dimethyl-9-(p-toluenesulfonyl)-9-aza-2,4-dioxa-1,2,3,4,4a,10,9,9a-octahydroanthracene

Guidance literature:: Multi-step reaction with 15 steps

1: 87 percent / CH₂Cl₂ / 52 h / Ambient temperature

2: 92 percent / DIBALH / toluene / 0.5 h / -15 °C

3: Et₃N / CH₂Cl₂ / 0.5 h / 0 °C

4: Et₃N / CH₂Cl₂ / 0.5 h / 0 °C

5: aq. citric acid*H₂O / diethyl ether; methanol / 0.83 h / Ambient temperature

6: L-(+)-diethyl tartrate, Ti(O-Pr)4, tert-butyl hydroperoxide / CH₂Cl₂ / 1.5 h / -20 °C

7: 95 percent / Et₃N / CH₂Cl₂ / 0.5 h / 0 °C

8: 87 percent / Zn, NaI / dimethylformamide / 0.25 h / 100 °C

9: 98 percent / DIBALH / toluene; hexane / 0.5 h / -15 °C

10: 96 percent / vanadyl acetylacetonate, tert-butyl hydroperoxide / CH₂Cl₂ / 2.5 h / 0 °C

11: 67 percent / TFA / toluene / 6 h / Ambient temperature

12: 92 percent / camphorsulfonic acid / acetone / 3 h / Ambient temperature

13: 99 percent / n-Bu₄NF / tetrahydrofuran / 15 h / Ambient temperature

14: pyridinium dichromate / CH₂Cl₂ / 4 h / Ambient temperature

15: MnO₂, KCN, AcOH / benzene / 13 h / Ambient temperature

With tert.-butylhydroperoxide; potassium cyanide; manganese(IV) oxide; dipyridinium dichromate; titanium tetra-n-propoxide; diethyl (2R,3R)-tartrate; vanadyl acetylacetonate; camphor-10-sulfonic acid; tetrabutyl ammonium fluoride; diisobutylaluminium hydride; acetic acid; triethylamine; trifluoroacetic acid; citric acid; sodium iodide; zinc; In tetrahydrofuran; methanol; diethyl ether; hexane; dichloromethane; N,N-dimethyl-formamide; acetone; toluene; benzene;
DOI:10.1016/0040-4020(96)00608-4