(3aR,11R,11aR,11bS)-9-Benzyloxy-5-oxo-1,2,3,3a,4,5,10,11,11a,11b-decahydro-5a-aza-benzo[cd]fluoranthene-11-carbonyl azide

Base Information

• Chemical Name: (3aR,11R,11aR,11bS)-9-Benzyloxy-5-oxo-1,2,3,3a,4,5,10,11,11a,11b-decahydro-5a-aza-benzo[cd]fluoranthene-11-carbonyl azide
• CAS No.: 1027905-47-0
• Molecular Formula: C₂₆H₂₄N₄O₃
• Molecular Weight: 440.502
• Mol file: 1027905-47-0.mol

Synonyms:(3aR,11R,11aR,11bS)-9-Benzyloxy-5-oxo-1,2,3,3a,4,5,10,11,11a,11b-decahydro-5a-aza-benzo[cd]fluoranthene-11-carbonyl azide

Chemical Property of (3aR,11R,11aR,11bS)-9-Benzyloxy-5-oxo-1,2,3,3a,4,5,10,11,11a,11b-decahydro-5a-aza-benzo[cd]fluoranthene-11-carbonyl azide

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (3aR,11R,11aR,11bS)-9-Benzyloxy-5-oxo-1,2,3,3a,4,5,10,11,11a,11b-decahydro-5a-aza-benzo[cd]fluoranthene-11-carbonyl azide

There total 12 articles about (3aR,11R,11aR,11bS)-9-Benzyloxy-5-oxo-1,2,3,3a,4,5,10,11,11a,11b-decahydro-5a-aza-benzo[cd]fluoranthene-11-carbonyl azide 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:

(R)-2-cyclohexen-1-ol (3413-44-3) → (3aR,11R,11aR,11bS)-9-Benzyloxy-5-oxo-1,2,3,3a,4,5,10,11,11a,11b-decahydro-5a-aza-benzo[cd]fluoranthene-11-carbonyl azide (1027905-47-0)

Guidance literature:

Multi-step reaction with 7 steps

1: o-nitrophenol / 9 h / 170 °C

2: 1N aq. NaOH / methanol / 12 h / Ambient temperature

3: 91.9 percent / SOCl₂ / benzene / 1.5 h / Heating

4: 1.) NaH / 1.) THF, 0 deg C, 0.5 h, 2.) THF, 0 deg C, 1 h

5: 2.) 4N HCl/dioxane / 1.) mesitylene, reflux, 24 h, 2.) mesitylene, 85 deg C, 6 h

6: Et₃N / acetone / 0.5 h / 0 °C

7: aq. NaN₃ / 1 h / 0 °C

With hydrogenchloride; sodium hydroxide; thionyl chloride; sodium azide; sodium hydride; triethylamine; 2-hydroxynitrobenzene; In methanol; acetone; benzene;

DOI:10.1016/0957-4166(96)00199-1

Reference yield:

C29H29NO6 → (3aR,11R,11aR,11bS)-9-Benzyloxy-5-oxo-1,2,3,3a,4,5,10,11,11a,11b-decahydro-5a-aza-benzo[cd]fluoranthene-11-carbonyl azide (1027905-47-0)

Guidance literature:

With sodium azide; at 0 ℃; for 1h;

DOI:10.1016/0957-4166(96)00199-1

Reference yield:

(1R,2R)-1-acetoxy-2-iodocyclohexane (144300-25-4) → (3aR,11R,11aR,11bS)-9-Benzyloxy-5-oxo-1,2,3,3a,4,5,10,11,11a,11b-decahydro-5a-aza-benzo[cd]fluoranthene-11-carbonyl azide (1027905-47-0)

Guidance literature:

Multi-step reaction with 9 steps

1: DBU / 120 °C

2: 86.9 percent / 1N aq. NaOH / methanol / Ambient temperature

3: o-nitrophenol / 9 h / 170 °C

4: 1N aq. NaOH / methanol / 12 h / Ambient temperature

5: 91.9 percent / SOCl₂ / benzene / 1.5 h / Heating

6: 1.) NaH / 1.) THF, 0 deg C, 0.5 h, 2.) THF, 0 deg C, 1 h

7: 2.) 4N HCl/dioxane / 1.) mesitylene, reflux, 24 h, 2.) mesitylene, 85 deg C, 6 h

8: Et₃N / acetone / 0.5 h / 0 °C

9: aq. NaN₃ / 1 h / 0 °C

With hydrogenchloride; sodium hydroxide; thionyl chloride; sodium azide; sodium hydride; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; 2-hydroxynitrobenzene; In methanol; acetone; benzene;

DOI:10.1016/0957-4166(96)00199-1

upstream raw materials:

(1R,2R)-1-acetoxy-2-iodocyclohexane

(1R, 2R)-2-(phenylthio)cyclohexyl acetate

(R)-2-cyclohexen-1-ol

(-)-(R)-cyclohex-2-enylacetic acid

Downstream raw materials:

<3aR-(3aα,12α,12aα,12bα)>-12-amino-2,3,3a,4,11,12,12a,12b-octahydro-10-hydroxyisoquino<2,1,8-lma>carbazol-2(1H)-one hydrochloride

((3aR,11R,11aR,11bS)-9-Benzyloxy-5-oxo-1,2,3,3a,4,5,10,11,11a,11b-decahydro-5a-aza-benzo[cd]fluoranthen-11-yl)-carbamic acid benzyl ester