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

Base Information

• Chemical Name: (4aS,9aS)-9a-(3,4-dimethyl-3-pentenyl)-3,3-dimethyl-9-(p-toluenesulfonyl)-9-aza-2,4-dioxa-1,2,3,4,4a,10,9,9a-octahydroanthracene-6-carbaldehyde
• CAS No.: 181369-04-0
• Molecular Formula: C₂₈H₃₅NO₅S
• Molecular Weight: 497.656
• Mol file: 181369-04-0.mol

Synonyms:

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 21 articles about (4aS,9aS)-9a-(3,4-dimethyl-3-pentenyl)-3,3-dimethyl-9-(p-toluenesulfonyl)-9-aza-2,4-dioxa-1,2,3,4,4a,10,9,9a-octahydroanthracene-6-carbaldehyde 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:

(4aS,9aS)-9a-(3,4-dimethyl-3-pentenyl)-6-hydroxymethyl-3,3-dimethyl-9-(p-toluenesulfonyl)-9-aza-2,4-dioxa-1,2,3,4,4a,10,9,9a-octahydroanthracene (181369-03-9) → (4aS,9aS)-9a-(3,4-dimethyl-3-pentenyl)-3,3-dimethyl-9-(p-toluenesulfonyl)-9-aza-2,4-dioxa-1,2,3,4,4a,10,9,9a-octahydroanthracene-6-carbaldehyde (181369-04-0)

Guidance literature:

With dipyridinium dichromate; In dichloromethane; for 4h; Ambient temperature;

DOI:10.1016/0040-4020(96)00608-4

Reference yield:

ethyl 4-amino-3-(2-propenyl)benzoate (59816-84-1) → (4aS,9aS)-9a-(3,4-dimethyl-3-pentenyl)-3,3-dimethyl-9-(p-toluenesulfonyl)-9-aza-2,4-dioxa-1,2,3,4,4a,10,9,9a-octahydroanthracene-6-carbaldehyde (181369-04-0)

Guidance literature:

Multi-step reaction with 18 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

With pyridine; 1H-imidazole; tert.-butylhydroperoxide; 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; triethylamine; trifluoroacetic acid; citric acid; sodium iodide; zinc; In tetrahydrofuran; methanol; diethyl ether; hexane; dichloromethane; N,N-dimethyl-formamide; acetone; toluene;

DOI:10.1016/0040-4020(96)00608-4

Reference yield:

methyl 5,6-dimethyl-2-triphenylphosphoranylidene-5-heptenoate (119139-47-8) → (4aS,9aS)-9a-(3,4-dimethyl-3-pentenyl)-3,3-dimethyl-9-(p-toluenesulfonyl)-9-aza-2,4-dioxa-1,2,3,4,4a,10,9,9a-octahydroanthracene-6-carbaldehyde (181369-04-0)

Guidance literature:

Multi-step reaction with 14 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

With tert.-butylhydroperoxide; dipyridinium dichromate; titanium tetra-n-propoxide; diethyl (2R,3R)-tartrate; vanadyl acetylacetonate; camphor-10-sulfonic acid; tetrabutyl ammonium fluoride; diisobutylaluminium hydride; triethylamine; trifluoroacetic acid; citric acid; sodium iodide; zinc; In tetrahydrofuran; methanol; diethyl ether; hexane; dichloromethane; N,N-dimethyl-formamide; acetone; toluene;

DOI:10.1016/0040-4020(96)00608-4

upstream raw materials:

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

ethyl 4-amino-3-(2-propenyl)benzoate

methyl 5,6-dimethyl-2-triphenylphosphoranylidene-5-heptenoate

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

Downstream raw materials:

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

(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