benzyl N-<(3aβ,12β,12aβ,12bβ)-9-(benzyloxy)-1,2,3,3a,4,5,11,12,12a,12b-decahydro-3aβ-ethyl-5-oxoisoquino<2,1,8-lma>carbazol-12-yl>carbamate

Base Information

• Chemical Name: benzyl N-<(3aβ,12β,12aβ,12bβ)-9-(benzyloxy)-1,2,3,3a,4,5,11,12,12a,12b-decahydro-3aβ-ethyl-5-oxoisoquino<2,1,8-lma>carbazol-12-yl>carbamate
• CAS No.: 103558-61-8
• Molecular Formula: C₃₅H₃₆N₂O₄
• Molecular Weight: 548.682
• Mol file: 103558-61-8.mol

Synonyms:

Chemical Property of benzyl N-<(3aβ,12β,12aβ,12bβ)-9-(benzyloxy)-1,2,3,3a,4,5,11,12,12a,12b-decahydro-3aβ-ethyl-5-oxoisoquino<2,1,8-lma>carbazol-12-yl>carbamate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of benzyl N-<(3aβ,12β,12aβ,12bβ)-9-(benzyloxy)-1,2,3,3a,4,5,11,12,12a,12b-decahydro-3aβ-ethyl-5-oxoisoquino<2,1,8-lma>carbazol-12-yl>carbamate

There total 9 articles about benzyl N-<(3aβ,12β,12aβ,12bβ)-9-(benzyloxy)-1,2,3,3a,4,5,11,12,12a,12b-decahydro-3aβ-ethyl-5-oxoisoquino<2,1,8-lma>carbazol-12-yl>carbamate 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:

methyl (E)-3-<5-(benzyloxy)-1H-indol-3-yl>-2-propenoate (103581-94-8) → benzyl N-<(3aβ,12β,12aβ,12bβ)-9-(benzyloxy)-1,2,3,3a,4,5,11,12,12a,12b-decahydro-3aβ-ethyl-5-oxoisoquino<2,1,8-lma>carbazol-12-yl>carbamate (103558-61-8)

Guidance literature:

Multi-step reaction with 8 steps

1: 75.1 percent / toluene / 20 h / Heating

2: 1.) NaH / 1.) DMF, RT, 30 min, 2.) DMF, 0.5 h

3: 2.) 15percent ethanol. HCl / 1.) mesitylene, reflux, 12 h, 2.) mesitylene, reflux, 0.5 h

4: 65.4 percent / tetrakis(triphenylphosphine)palladium⁽⁰⁾, Ph₃P, 2-ethylhexanoic acid / ethyl acetate; CHCl₃ / 8 h / Ambient temperature

5: ethyl chloroformate, Et₃N / acetone / 0.5 h

6: NaN₃ / acetone; H₂O / 0.5 h / 0 °C

7: xylene / 0.5 h / Heating

8: xylene / 1 h / Heating

With hydrogenchloride; tetrakis(triphenylphosphine) palladium⁽⁰⁾; sodium azide; 2-Ethylhexanoic acid; chloroformic acid ethyl ester; sodium hydride; triethylamine; triphenylphosphine; In chloroform; water; ethyl acetate; acetone; toluene; xylene;

DOI:10.1021/jm00083a004

Reference yield:

allyl (E)-3-<5-(benzyloxy)-1H-indol-3-yl>-2-propenoate (103580-91-2) → benzyl N-<(3aβ,12β,12aβ,12bβ)-9-(benzyloxy)-1,2,3,3a,4,5,11,12,12a,12b-decahydro-3aβ-ethyl-5-oxoisoquino<2,1,8-lma>carbazol-12-yl>carbamate (103558-61-8)

Guidance literature:

Multi-step reaction with 7 steps

1: 1.) NaH / 1.) DMF, RT, 30 min, 2.) DMF, 0.5 h

2: 2.) 15percent ethanol. HCl / 1.) mesitylene, reflux, 12 h, 2.) mesitylene, reflux, 0.5 h

3: 65.4 percent / tetrakis(triphenylphosphine)palladium⁽⁰⁾, Ph₃P, 2-ethylhexanoic acid / ethyl acetate; CHCl₃ / 8 h / Ambient temperature

4: ethyl chloroformate, Et₃N / acetone / 0.5 h

5: NaN₃ / acetone; H₂O / 0.5 h / 0 °C

6: xylene / 0.5 h / Heating

7: xylene / 1 h / Heating

With hydrogenchloride; tetrakis(triphenylphosphine) palladium⁽⁰⁾; sodium azide; 2-Ethylhexanoic acid; chloroformic acid ethyl ester; sodium hydride; triethylamine; triphenylphosphine; In chloroform; water; ethyl acetate; acetone; xylene;

DOI:10.1021/jm00083a004

Reference yield:

(3aR,4R,11aR,11bR)-7-Benzyloxy-11a-ethyl-10-oxo-1,2,3,3a,4,5,10,11,11a,11b-decahydro-9b-aza-benzo[cd]fluoranthene-4-carbonyl chloride → benzyl N-<(3aβ,12β,12aβ,12bβ)-9-(benzyloxy)-1,2,3,3a,4,5,11,12,12a,12b-decahydro-3aβ-ethyl-5-oxoisoquino<2,1,8-lma>carbazol-12-yl>carbamate (103558-61-8)

Guidance literature:

Multi-step reaction with 3 steps

1: NaN₃ / acetone; H₂O / 0.5 h / 0 °C

2: xylene / 0.5 h / Heating

3: xylene / 1 h / Heating

With sodium azide; In water; acetone; xylene;

DOI:10.1021/jm00083a004

upstream raw materials:

benzyl alcohol

methyl (E)-3-<5-(benzyloxy)-1H-indol-3-yl>-2-propenoate

allyl (E)-3-<5-(benzyloxy)-1H-indol-3-yl>-2-propenoate

allyl (E)-3-<5-(benzyloxy)-1-<2-(1-ethyl-2-cyclohexen-1-yl)acetyl>-1H-indol-3-yl>-2-propenoate