(E,3aR^*,5S^*,6aR^*,11bS^*)-5-<1-<<(tert-butyldimethylsilyl)oxy>methyl>propenyl>-7-(methoxycarbonyl)-3-(phenylmethyl)-2,3,3a,4,5,6,6a,7-octahydro-1H-pyrrolo<2,3-d>carbazole

Base Information

• Chemical Name: (E,3aR^*,5S^*,6aR^*,11bS^*)-5-<1-<<(tert-butyldimethylsilyl)oxy>methyl>propenyl>-7-(methoxycarbonyl)-3-(phenylmethyl)-2,3,3a,4,5,6,6a,7-octahydro-1H-pyrrolo<2,3-d>carbazole
• CAS No.: 97552-36-8
• Molecular Formula: C₃₃H₄₆N₂O₃Si
• Molecular Weight: 546.825

Synonyms:(E,3aR^*,5S^*,6aR^*,11bS^*)-5-<1-<<(tert-butyldimethylsilyl)oxy>methyl>propenyl>-7-(methoxycarbonyl)-3-(phenylmethyl)-2,3,3a,4,5,6,6a,7-octahydro-1H-pyrrolo<2,3-d>carbazole

Chemical Property of (E,3aR^*,5S^*,6aR^*,11bS^*)-5-<1-<<(tert-butyldimethylsilyl)oxy>methyl>propenyl>-7-(methoxycarbonyl)-3-(phenylmethyl)-2,3,3a,4,5,6,6a,7-octahydro-1H-pyrrolo<2,3-d>carbazole

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (E,3aR^*,5S^*,6aR^*,11bS^*)-5-<1-<<(tert-butyldimethylsilyl)oxy>methyl>propenyl>-7-(methoxycarbonyl)-3-(phenylmethyl)-2,3,3a,4,5,6,6a,7-octahydro-1H-pyrrolo<2,3-d>carbazole

There total 19 articles about (E,3aR^*,5S^*,6aR^*,11bS^*)-5-<1-<<(tert-butyldimethylsilyl)oxy>methyl>propenyl>-7-(methoxycarbonyl)-3-(phenylmethyl)-2,3,3a,4,5,6,6a,7-octahydro-1H-pyrrolo<2,3-d>carbazole 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: 73.0%

methyl chloroformate (79-22-1) + (E,3aR*,5R*,11bR*)-5-<1-<<(tert-butyldimethylsilyl)oxy>methyl>propenyl>-3-(phenylmethyl)-2,3,3a,4,5,6,6a,7-octahydro-1H-pyrrolo<2,3-d>carbazole (97552-35-7) → (E,3aR*,5S*,6aR*,11bS*)-5-<1-<<(tert-butyldimethylsilyl)oxy>methyl>propenyl>-7-(methoxycarbonyl)-3-(phenylmethyl)-2,3,3a,4,5,6,6a,7-octahydro-1H-pyrrolo<2,3-d>carbazole (97552-36-8)

Guidance literature:

With 1,2,2,6,6-pentamethylpiperidine; In dichloromethane; at 0 ℃; for 3.5h;

DOI:10.1021/jo00221a012

Reference yield:

ethyl 2-(3-cyclopentenyl)-2(E)-butenoate (97552-23-3) → (E,3aR*,5S*,6aR*,11bS*)-5-<1-<<(tert-butyldimethylsilyl)oxy>methyl>propenyl>-7-(methoxycarbonyl)-3-(phenylmethyl)-2,3,3a,4,5,6,6a,7-octahydro-1H-pyrrolo<2,3-d>carbazole (97552-36-8)

Guidance literature:

Multi-step reaction with 14 steps

1: m-chloroperbenzoic acid, NaHCO₃ / CH₂Cl₂ / 0.5 h / 0 °C

2: 78 percent / diisobutylaluminum hydride / toluene / 0.17 h / -78 °C

3: imidazole / dimethylformamide / 4.3 h / Ambient temperature

4: 1.) trimethylaluminum, 3.) NaF

5: triethylamine / CH₂Cl₂ / 1 h / 0 °C

6: 1.) oxalyl chloride, dimethylsulfoxide, 2.) Et₃N / 1.) CH₂Cl₂, -78 deg C, 15 min, 2.) CH₂Cl₂, -78 deg C, 10 min

7: 1.) n-BuLi / 1.) hexane, THF, -78 deg C, 40 min, 2.) hexane, THF, -78 deg C, 30 min

8: 1.) n-BuLi / 1.) hexane, THF, from -78 deg C to RT, 15 min, 2.) hexane, THF, from -78 deg C to RT, 64 h

9: 96 percent / KOH / methanol; H₂O / 18 h / Heating

10: 97 percent / tetrahydrofuran / 8 h / Ambient temperature

11: 98 percent / triethylamine, 4-(dimethylamino)pyridine / dimethylformamide / 2.5 h / Ambient temperature

12: 10-camphorsulfonic acid, sodium sulfate / toluene / 0.67 h / Heating

13: LiAlH₄ / tetrahydrofuran / 2.5 h / 0 °C

14: 73 percent / 1,2,2,6,6-pentamethylpiperidine (PMP) / CH₂Cl₂ / 3.5 h / 0 °C

With 1,2,2,6,6-pentamethylpiperidine; 1H-imidazole; dmap; potassium hydroxide; lithium aluminium tetrahydride; n-butyllithium; oxalyl dichloride; (1S)-10-camphorsulfonic acid; trimethylaluminum; diisobutylaluminium hydride; sodium hydrogencarbonate; sodium fluoride; dimethyl sulfoxide; sodium sulfate; triethylamine; 3-chloro-benzenecarboperoxoic acid; In tetrahydrofuran; methanol; dichloromethane; water; N,N-dimethyl-formamide; toluene;

DOI:10.1021/jo00221a012

Reference yield:

2-Cyclopent-3-enyl-3-oxo-butyric acid ethyl ester (55839-23-1) → (E,3aR*,5S*,6aR*,11bS*)-5-<1-<<(tert-butyldimethylsilyl)oxy>methyl>propenyl>-7-(methoxycarbonyl)-3-(phenylmethyl)-2,3,3a,4,5,6,6a,7-octahydro-1H-pyrrolo<2,3-d>carbazole (97552-36-8)

Guidance literature:

Multi-step reaction with 17 steps

1: 59 percent / zinc borohydride / diethyl ether / 0.33 h / 0 °C

2: triethylamine / CH₂Cl₂ / 1 h / 0 °C

3: 1,8-diazabicyclo<5.4.0>undec-7-ene (DBU) / toluene / Ambient temperature

4: m-chloroperbenzoic acid, NaHCO₃ / CH₂Cl₂ / 0.5 h / 0 °C

5: 78 percent / diisobutylaluminum hydride / toluene / 0.17 h / -78 °C

6: imidazole / dimethylformamide / 4.3 h / Ambient temperature

7: 1.) trimethylaluminum, 3.) NaF

8: triethylamine / CH₂Cl₂ / 1 h / 0 °C

9: 1.) oxalyl chloride, dimethylsulfoxide, 2.) Et₃N / 1.) CH₂Cl₂, -78 deg C, 15 min, 2.) CH₂Cl₂, -78 deg C, 10 min

10: 1.) n-BuLi / 1.) hexane, THF, -78 deg C, 40 min, 2.) hexane, THF, -78 deg C, 30 min

11: 1.) n-BuLi / 1.) hexane, THF, from -78 deg C to RT, 15 min, 2.) hexane, THF, from -78 deg C to RT, 64 h

12: 96 percent / KOH / methanol; H₂O / 18 h / Heating

13: 97 percent / tetrahydrofuran / 8 h / Ambient temperature

14: 98 percent / triethylamine, 4-(dimethylamino)pyridine / dimethylformamide / 2.5 h / Ambient temperature

15: 10-camphorsulfonic acid, sodium sulfate / toluene / 0.67 h / Heating

16: LiAlH₄ / tetrahydrofuran / 2.5 h / 0 °C

17: 73 percent / 1,2,2,6,6-pentamethylpiperidine (PMP) / CH₂Cl₂ / 3.5 h / 0 °C

With 1,2,2,6,6-pentamethylpiperidine; 1H-imidazole; dmap; potassium hydroxide; lithium aluminium tetrahydride; n-butyllithium; oxalyl dichloride; zinc borohydride; (1S)-10-camphorsulfonic acid; trimethylaluminum; diisobutylaluminium hydride; sodium hydrogencarbonate; sodium fluoride; dimethyl sulfoxide; 1,8-diazabicyclo[5.4.0]undec-7-ene; sodium sulfate; triethylamine; 3-chloro-benzenecarboperoxoic acid; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; water; N,N-dimethyl-formamide; toluene;

DOI:10.1021/jo00221a012

upstream raw materials:

methyl chloroformate

(E,3aR^*,5R^*,11bR^*)-5-<1-<<(tert-butyldimethylsilyl)oxy>methyl>propenyl>-3-(phenylmethyl)-2,3,3a,4,5,6,6a,7-octahydro-1H-pyrrolo<2,3-d>carbazole

ethyl 2-(3-cyclopentenyl)-2(E)-butenoate

2-Cyclopent-3-enyl-3-oxo-butyric acid ethyl ester

Post a RFQ

Cas No.:

Product Name:

Quantity:

Please select Metric Ton KG G Pound L ML

Email:

Company name:

Valid Period:

Detailed Requirements:

• Sample
• MOQ
• GMP
• FDA
• Price
  FOB CIF CFR EXW
• Urgent purchase

Enter 15 to 2000 letters.Word count: 0 letters

Attach files(File Format: Jpeg, Jpg, Gif, Png, PDF, PPT, Zip, Rar,Word or Excel Maximum File Size: 3MB)

Remove

Submit

1

What can I do for you?
Get Best Price

Get Best Price for 97552-36-8 (E,3aR^*,5S^*,6aR^*,11bS^*)-5-<1-<<(tert-butyldimethylsilyl)oxy>methyl>propenyl>-7-(methoxycarbonyl)-3-(phenylmethyl)-2,3,3a,4,5,6,6a,7-octahydro-1H-pyrrolo<2,3-d>carbazole

Send

Send

Metric Ton KG G Pound L ML

Send

Send