benzyl (4bR,4cR,5aS,10bS)-1,2-dimethoxy-4b,5a,10b,12-tetrahydro[1,3]benzodioxolo[5,6-c]oxireno[a]phenanthridine-11(4cH)-carboxylate

Base Information

• Chemical Name: benzyl (4bR,4cR,5aS,10bS)-1,2-dimethoxy-4b,5a,10b,12-tetrahydro[1,3]benzodioxolo[5,6-c]oxireno[a]phenanthridine-11(4cH)-carboxylate
• CAS No.: 929189-28-6
• Molecular Formula: C₂₈H₂₅NO₇
• Molecular Weight: 487.509
• Mol file: 929189-28-6.mol

Synonyms:benzyl (4bR,4cR,5aS,10bS)-1,2-dimethoxy-4b,5a,10b,12-tetrahydro[1,3]benzodioxolo[5,6-c]oxireno[a]phenanthridine-11(4cH)-carboxylate

Chemical Property of benzyl (4bR,4cR,5aS,10bS)-1,2-dimethoxy-4b,5a,10b,12-tetrahydro[1,3]benzodioxolo[5,6-c]oxireno[a]phenanthridine-11(4cH)-carboxylate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of benzyl (4bR,4cR,5aS,10bS)-1,2-dimethoxy-4b,5a,10b,12-tetrahydro[1,3]benzodioxolo[5,6-c]oxireno[a]phenanthridine-11(4cH)-carboxylate

There total 8 articles about benzyl (4bR,4cR,5aS,10bS)-1,2-dimethoxy-4b,5a,10b,12-tetrahydro[1,3]benzodioxolo[5,6-c]oxireno[a]phenanthridine-11(4cH)-carboxylate 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: 100.0%

benzyl (4bR,5S,6S,11bS)-5-bromo-6-hydroxy-1,2-dimethoxy-4b,6,11b,13-tetrahydro[1,3]benzodioxolo[5,6-c]phenanthridine-12(5H)-carboxylate (929189-27-5) → benzyl (4bR,4cR,5aS,10bS)-1,2-dimethoxy-4b,5a,10b,12-tetrahydro[1,3]benzodioxolo[5,6-c]oxireno[a]phenanthridine-11(4cH)-carboxylate (929189-28-6)

Guidance literature:

With potassium tert-butylate; In tetrahydrofuran; at -78 ℃; for 0.75h;

DOI:10.1002/anie.200603945

Reference yield:

C17H29BO6 → benzyl (4bR,4cR,5aS,10bS)-1,2-dimethoxy-4b,5a,10b,12-tetrahydro[1,3]benzodioxolo[5,6-c]oxireno[a]phenanthridine-11(4cH)-carboxylate (929189-28-6)

Guidance literature:

Multi-step reaction with 7 steps

1: 2.11 g / NH₄Cl / tetrahydrofuran; hexane; H₂O / 0 °C / pH 5 - 6

2: cesium carbonate; (Sa)-2,2'-bis(di(4-methylphenyl)phosphanyl)-1,1'-binaphthyl / bis(acetonitrile)dichloropalladium(II) / methanol / 6 h / 20 °C

3: 75 percent / aq. HCl / propan-2-ol; tetrahydrofuran / 8 h / 20 °C

4: triphenylphosphine; carbon tetrabromide / CH₂Cl₂ / 1 h / 0 °C

5: 581 mg / sodium hydride / dimethylformamide / 1.5 h / 0 °C

6: 75 percent / N-bromosuccinimide / tetrahydrofuran; H₂O / 1.5 h / 20 °C

7: 100 percent / potassium tert-butoxide / tetrahydrofuran / 0.75 h / -78 °C

With hydrogenchloride; N-Bromosuccinimide; carbon tetrabromide; potassium tert-butylate; sodium hydride; ammonium chloride; caesium carbonate; triphenylphosphine; dichloro bis(acetonitrile) palladium(II); In tetrahydrofuran; methanol; hexane; dichloromethane; water; N,N-dimethyl-formamide; isopropyl alcohol;

DOI:10.1002/anie.200603945

Reference yield:

2,3-dimethoxybenzyl alcohol (5653-67-8) → benzyl (4bR,4cR,5aS,10bS)-1,2-dimethoxy-4b,5a,10b,12-tetrahydro[1,3]benzodioxolo[5,6-c]oxireno[a]phenanthridine-11(4cH)-carboxylate (929189-28-6)

Guidance literature:

Multi-step reaction with 10 steps

1.1: 89 percent / N-bromosuccinimide / tetrahydrofuran / 0.5 h / 20 °C

2.1: 72 percent / lithium bromide; p-toluenesulfonic acid monohydrate / 14 h / 20 °C

3.1: n-butyllithium / tetrahydrofuran; hexane / 0.58 h / -78 °C

3.2: tetrahydrofuran; hexane / 18 h / -78 - 20 °C

4.1: 2.11 g / NH₄Cl / tetrahydrofuran; hexane; H₂O / 0 °C / pH 5 - 6

5.1: cesium carbonate; (Sa)-2,2'-bis(di(4-methylphenyl)phosphanyl)-1,1'-binaphthyl / bis(acetonitrile)dichloropalladium(II) / methanol / 6 h / 20 °C

6.1: 75 percent / aq. HCl / propan-2-ol; tetrahydrofuran / 8 h / 20 °C

7.1: triphenylphosphine; carbon tetrabromide / CH₂Cl₂ / 1 h / 0 °C

8.1: 581 mg / sodium hydride / dimethylformamide / 1.5 h / 0 °C

9.1: 75 percent / N-bromosuccinimide / tetrahydrofuran; H₂O / 1.5 h / 20 °C

10.1: 100 percent / potassium tert-butoxide / tetrahydrofuran / 0.75 h / -78 °C

With hydrogenchloride; N-Bromosuccinimide; n-butyllithium; carbon tetrabromide; potassium tert-butylate; sodium hydride; ammonium chloride; caesium carbonate; toluene-4-sulfonic acid; triphenylphosphine; lithium bromide; dichloro bis(acetonitrile) palladium(II); In tetrahydrofuran; methanol; hexane; dichloromethane; water; N,N-dimethyl-formamide; isopropyl alcohol;

DOI:10.1002/anie.200603945

upstream raw materials:

benzyl (4bR,5S,6S,11bS)-5-bromo-6-hydroxy-1,2-dimethoxy-4b,6,11b,13-tetrahydro[1,3]benzodioxolo[5,6-c]phenanthridine-12(5H)-carboxylate

benzyl (5S,6R)-6-(3,4-dimethoxy-2-((methoxymethoxy)methyl)phenyl)-5,6-dihydronaphtho[2,3-d][1,3]dioxol-5-ylcarbamate

benzyl (5S,6R)-6-[2-(hydroxymethyl)-3,4-dimethoxyphenyl]-5,6-dihydronaphtho[2,3-d][1,3]dioxol-5-ylcarbamate

benzyl (4bR,11bS)-1,2-dimethoxy-4b,13-dihydro[1,3]benzodioxolo[5,6-c]phenanthridine-12(11bH)-carboxylate

Downstream raw materials:

(4bR,5S,11bS)-1,2-dimethoxy-12-methyl-4b,5,6,11b,12,13-hexahydro[1,3]benzodioxolo[5,6-c]phenanthridin-5-ol

C₂₈H₂₇NO₈

Refernces

• 1、 McManus, Helen A.,Fleming, Matthew J.,Lautens, Mark. "Enantioselective total synthesis of (+)-homochelidonine by a Pd II-catalyzed asymmetric ring-opening reaction of a meso-azabicyclic alkene with an aryl boronic acid". . p. 433 - 436. Retrieved 2008/02/02.