20H-6,20-Methano-11,15-metheno-1H,8H-benzo[g]pyrido[2,1-d][1,5]oxaazacyclohexadecin-8-one,2,3,4,4a,5,6,9,10-octahydro-14-hydroxy-17,18-dimethoxy-, (4aR,6S,20S)- (9CI)

Base Information

• Chemical Name: 20H-6,20-Methano-11,15-metheno-1H,8H-benzo[g]pyrido[2,1-d][1,5]oxaazacyclohexadecin-8-one,2,3,4,4a,5,6,9,10-octahydro-14-hydroxy-17,18-dimethoxy-, (4aR,6S,20S)- (9CI)
• CAS No.: 17349-05-2
• Molecular Formula: C₂₆H₃₁NO₅
• Molecular Weight: 437.536
• Mol file: 17349-05-2.mol

Synonyms:Decamine(7CI); Decamine (alkaloid) (8CI); Lythran-12-one,13,14-dihydro-2'-hydroxy-4'',5''-dimethoxy-, (10a)-; Dihydrocryogenine; Dihydrovertine

Chemical Property of 20H-6,20-Methano-11,15-metheno-1H,8H-benzo[g]pyrido[2,1-d][1,5]oxaazacyclohexadecin-8-one,2,3,4,4a,5,6,9,10-octahydro-14-hydroxy-17,18-dimethoxy-, (4aR,6S,20S)- (9CI)

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of 20H-6,20-Methano-11,15-metheno-1H,8H-benzo[g]pyrido[2,1-d][1,5]oxaazacyclohexadecin-8-one,2,3,4,4a,5,6,9,10-octahydro-14-hydroxy-17,18-dimethoxy-, (4aR,6S,20S)- (9CI)

There total 17 articles about 20H-6,20-Methano-11,15-metheno-1H,8H-benzo[g]pyrido[2,1-d][1,5]oxaazacyclohexadecin-8-one,2,3,4,4a,5,6,9,10-octahydro-14-hydroxy-17,18-dimethoxy-, (4aR,6S,20S)- (9CI) 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: 80.0%

C33H36N2O7 → Decinin (10183-64-9,17349-05-2,57550-21-7)

Guidance literature:

With 20 % Pd(OH)2/C; hydrogen; In ethyl acetate; for 6h; Inert atmosphere;

DOI:10.1021/ol3015573

Reference yield:

piperidine (110-89-4) → Decinin (10183-64-9,17349-05-2,57550-21-7)

Guidance literature:

Multi-step reaction with 10 steps

1.1: perchloric acid / diethyl ether; ethanol / Inert atmosphere

2.1: piperidine / benzene / 6 h / Inert atmosphere; Reflux

3.1: diethyl ether / 0.5 h / -20 - 20 °C / Inert atmosphere

4.1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 1 h / 0 °C / Inert atmosphere; Molecular sieve

4.2: 1 h / 0 - 20 °C / Inert atmosphere; Molecular sieve

5.1: L-Selectride / tetrahydrofuran / 1 h / -78 °C / Inert atmosphere

6.1: dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / dichloromethane / 24 h / 20 °C / Inert atmosphere

7.1: palladium on carbon; hydrogen / ethyl acetate / 6 h / Inert atmosphere

8.1: potassium carbonate / acetone / Inert atmosphere; Reflux

9.1: oxovanadium(V) fluoride; trifluoroacetic acid / dichloromethane / 1 h / 0 - 20 °C / Inert atmosphere

10.1: 20 % Pd(OH)2/C; hydrogen / ethyl acetate / 6 h / Inert atmosphere

With piperidine; dmap; perchloric acid; oxovanadium(V) fluoride; palladium on carbon; 20 % Pd(OH)2/C; hydrogen; L-Selectride; potassium carbonate; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; 3-chloro-benzenecarboperoxoic acid; trifluoroacetic acid; In tetrahydrofuran; diethyl ether; ethanol; dichloromethane; ethyl acetate; acetone; benzene;

DOI:10.1021/ol3015573

Reference yield:

C33H37NO5 → Decinin (10183-64-9,17349-05-2,57550-21-7)

Guidance literature:

Multi-step reaction with 4 steps

1: palladium on carbon; hydrogen / ethyl acetate / 6 h / Inert atmosphere

2: potassium carbonate / acetone / Inert atmosphere; Reflux

3: oxovanadium(V) fluoride; trifluoroacetic acid / dichloromethane / 1 h / 0 - 20 °C / Inert atmosphere

4: 20 % Pd(OH)2/C; hydrogen / ethyl acetate / 6 h / Inert atmosphere

With oxovanadium(V) fluoride; palladium on carbon; 20 % Pd(OH)2/C; hydrogen; potassium carbonate; trifluoroacetic acid; In dichloromethane; ethyl acetate; acetone;

DOI:10.1021/ol3015573

upstream raw materials:

piperidine

C₁₄H₂₀NO₂⁽¹⁺⁾*ClO₄^(1-)

C₁₇H₂₃NO₂

para-coumaric acid