(3aS,3bS,7S,19bS,E/Z)-7-benzyl-2,2-dimethyl-3b,4,6,7,8,10,13,19b-octahydrobis[1,3]dioxolo[4,5-c:4',5'-g][1,4,8]oxadiazacyclododeca[8,7-a]quinolin-5(3aH)-one

Base Information

• Chemical Name: (3aS,3bS,7S,19bS,E/Z)-7-benzyl-2,2-dimethyl-3b,4,6,7,8,10,13,19b-octahydrobis[1,3]dioxolo[4,5-c:4',5'-g][1,4,8]oxadiazacyclododeca[8,7-a]quinolin-5(3aH)-one
• CAS No.: 1440196-47-3
• Molecular Formula: C₂₈H₃₂N₂O₆
• Molecular Weight: 492.572
• Mol file: 1440196-47-3.mol

Synonyms:

Chemical Property of (3aS,3bS,7S,19bS,E/Z)-7-benzyl-2,2-dimethyl-3b,4,6,7,8,10,13,19b-octahydrobis[1,3]dioxolo[4,5-c:4',5'-g][1,4,8]oxadiazacyclododeca[8,7-a]quinolin-5(3aH)-one

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (3aS,3bS,7S,19bS,E/Z)-7-benzyl-2,2-dimethyl-3b,4,6,7,8,10,13,19b-octahydrobis[1,3]dioxolo[4,5-c:4',5'-g][1,4,8]oxadiazacyclododeca[8,7-a]quinolin-5(3aH)-one

There total 16 articles about (3aS,3bS,7S,19bS,E/Z)-7-benzyl-2,2-dimethyl-3b,4,6,7,8,10,13,19b-octahydrobis[1,3]dioxolo[4,5-c:4',5'-g][1,4,8]oxadiazacyclododeca[8,7-a]quinolin-5(3aH)-one 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:

2-((3aS,4S,10bS)-5-allyl-2,2-dimethyl-3a,4,5,10b-tetrahydrobis[1,3]dioxolo[4,5-c:4',5'-g]quinolin-4-yl)-N-((S)-1-(allyloxy)-3-phenylpropan-2-yl)acetamide (1440196-39-3) → (3aS,3bS,7S,19bS,E/Z)-7-benzyl-2,2-dimethyl-3b,4,6,7,8,10,13,19b-octahydrobis[1,3]dioxolo[4,5-c:4',5'-g][1,4,8]oxadiazacyclododeca[8,7-a]quinolin-5(3aH)-one (1440196-47-3)

Guidance literature:

With tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; In dichloromethane; at 40 ℃; for 12h; Inert atmosphere;

DOI:10.1021/ml400026n

Reference yield:

(E)-ethyl 3-(6-nitrobenzo[d][1,3]dioxol-5-yl)acrylate (94527-27-2) → (3aS,3bS,7S,19bS,E/Z)-7-benzyl-2,2-dimethyl-3b,4,6,7,8,10,13,19b-octahydrobis[1,3]dioxolo[4,5-c:4',5'-g][1,4,8]oxadiazacyclododeca[8,7-a]quinolin-5(3aH)-one (1440196-47-3)

Guidance literature:

Multi-step reaction with 10 steps

1: methanesulfonamide; AD-mix-α / water; tert-butyl alcohol / 40 h / 0 - 20 °C / Inert atmosphere

2: toluene-4-sulfonic acid / dichloromethane; acetone / 12 h / 20 °C / Inert atmosphere

3: lithium borohydride / tetrahydrofuran / 12 h / 20 °C / Inert atmosphere

4: triethylamine / dichloromethane; dimethyl sulfoxide / 8 h / 20 °C / Inert atmosphere

5: zinc; acetic acid / ethanol / 0.5 h / 20 °C / Inert atmosphere

6: potassium hexamethylsilazane / tetrahydrofuran; hexane / 0.5 h / -78 °C / Inert atmosphere

7: lithium hydroxide monohydrate / tetrahydrofuran; water / 4 h / 20 °C / Inert atmosphere

8: O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 12 h / 0 - 20 °C / Inert atmosphere

9: potassium carbonate / N,N-dimethyl-formamide / 30 h / 20 °C / Inert atmosphere

10: tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride / dichloromethane / 12 h / 40 °C / Inert atmosphere

With tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; lithium borohydride; lithium hydroxide monohydrate; methanesulfonamide; AD-mix-α; potassium hexamethylsilazane; potassium carbonate; O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; toluene-4-sulfonic acid; acetic acid; triethylamine; N-ethyl-N,N-diisopropylamine; zinc; In tetrahydrofuran; ethanol; hexane; dichloromethane; water; dimethyl sulfoxide; N,N-dimethyl-formamide; acetone; tert-butyl alcohol;

DOI:10.1021/ml400026n

Reference yield:

(S)-N-tert-butoxycarbonyl-2-amino-3-phenylpropanol (66605-57-0) → (3aS,3bS,7S,19bS,E/Z)-7-benzyl-2,2-dimethyl-3b,4,6,7,8,10,13,19b-octahydrobis[1,3]dioxolo[4,5-c:4',5'-g][1,4,8]oxadiazacyclododeca[8,7-a]quinolin-5(3aH)-one (1440196-47-3)

Guidance literature:

Multi-step reaction with 5 steps

1: sodium hydride / N,N-dimethyl-formamide / 16 h / 0 - 20 °C / Inert atmosphere

2: trifluoroacetic acid / tetrahydrofuran / 2 h / 0 - 20 °C / Inert atmosphere

3: O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 12 h / 0 - 20 °C / Inert atmosphere

4: potassium carbonate / N,N-dimethyl-formamide / 30 h / 20 °C / Inert atmosphere

5: tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride / dichloromethane / 12 h / 40 °C / Inert atmosphere

With tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; sodium hydride; potassium carbonate; O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine; trifluoroacetic acid; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1021/ml400026n

upstream raw materials:

(S)-N-tert-butoxycarbonyl-2-amino-3-phenylpropanol

(S)-tert-butyl (1-(allyloxy)-3-phenylpropan-2-yl)carbamate

(E)-ethyl 3-(6-nitrobenzo[d][1,3]dioxol-5-yl)acrylate

(S)-1-(allyloxy)-3-phenylpropan-2-amine