(S)-N-((3S,11bR)-9,11-bis(benzyloxy)-4-oxo-2,3,4,6,7,11b-hexahydro-1H-pyrido[2,1-a]isoquinolin-3-yl)-16-((4S,5S)-5-decyl-2,2-dimethyl-1,3-dioxolan-4-yl)-14-(methoxymethoxy)hexadecanamide

Base Information

• Chemical Name: (S)-N-((3S,11bR)-9,11-bis(benzyloxy)-4-oxo-2,3,4,6,7,11b-hexahydro-1H-pyrido[2,1-a]isoquinolin-3-yl)-16-((4S,5S)-5-decyl-2,2-dimethyl-1,3-dioxolan-4-yl)-14-(methoxymethoxy)hexadecanamide
• CAS No.: 949463-71-2
• Molecular Formula: C₆₀H₉₀N₂O₈
• Molecular Weight: 967.383
• Mol file: 949463-71-2.mol

Synonyms:(S)-N-((3S,11bR)-9,11-bis(benzyloxy)-4-oxo-2,3,4,6,7,11b-hexahydro-1H-pyrido[2,1-a]isoquinolin-3-yl)-16-((4S,5S)-5-decyl-2,2-dimethyl-1,3-dioxolan-4-yl)-14-(methoxymethoxy)hexadecanamide

Chemical Property of (S)-N-((3S,11bR)-9,11-bis(benzyloxy)-4-oxo-2,3,4,6,7,11b-hexahydro-1H-pyrido[2,1-a]isoquinolin-3-yl)-16-((4S,5S)-5-decyl-2,2-dimethyl-1,3-dioxolan-4-yl)-14-(methoxymethoxy)hexadecanamide

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (S)-N-((3S,11bR)-9,11-bis(benzyloxy)-4-oxo-2,3,4,6,7,11b-hexahydro-1H-pyrido[2,1-a]isoquinolin-3-yl)-16-((4S,5S)-5-decyl-2,2-dimethyl-1,3-dioxolan-4-yl)-14-(methoxymethoxy)hexadecanamide

There total 19 articles about (S)-N-((3S,11bR)-9,11-bis(benzyloxy)-4-oxo-2,3,4,6,7,11b-hexahydro-1H-pyrido[2,1-a]isoquinolin-3-yl)-16-((4S,5S)-5-decyl-2,2-dimethyl-1,3-dioxolan-4-yl)-14-(methoxymethoxy)hexadecanamide 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: 75.0%

(S)-16-((4S,5S)-5-decyl-2,2-dimethyl-1,3-dioxolan-4-yl)-14-(methoxymethoxy)hexadecanoic acid (949463-55-2) + (3S,11bR)-3-amino-9,11-bis(benzyloxy)-2,3,6,7-tetrahydro-1H-pyrido[2,1-a]isoquinolin-4(11bH)-one (949463-54-1) → (S)-N-((3S,11bR)-9,11-bis(benzyloxy)-4-oxo-2,3,4,6,7,11b-hexahydro-1H-pyrido[2,1-a]isoquinolin-3-yl)-16-((4S,5S)-5-decyl-2,2-dimethyl-1,3-dioxolan-4-yl)-14-(methoxymethoxy)hexadecanamide (949463-71-2)

Guidance literature:

With 1-hydroxybenzotriazol-hydrate; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; In dichloromethane; at 20 ℃; for 15h;

DOI:10.1021/jo070560h

Reference yield:

methyl 14-(benzyloxy)tetradecanoate (949463-61-0) → (S)-N-((3S,11bR)-9,11-bis(benzyloxy)-4-oxo-2,3,4,6,7,11b-hexahydro-1H-pyrido[2,1-a]isoquinolin-3-yl)-16-((4S,5S)-5-decyl-2,2-dimethyl-1,3-dioxolan-4-yl)-14-(methoxymethoxy)hexadecanamide (949463-71-2)

Guidance literature:

Multi-step reaction with 8 steps

1.1: n-butyllithium / tetrahydrofuran; hexane / 0.5 h / -78 °C

1.2: 93 percent / tetrahydrofuran; hexane / 2.5 h / -78 °C

2.1: 95 percent / 1,8-diazabicyclo[5.4.0]undec-7-ene; LiCl / acetonitrile / 1 h / 20 °C

3.1: 77 percent / (S)-(-)-1,1'-bi-2-naphthol; lithium aluminium hydride / tetrahydrofuran; ethanol / 2.5 h / -78 °C

4.1: 97 percent / N,N'-diisopropylethylamine / CH₂Cl₂ / 2 h / 20 °C

5.1: 80 percent / H₂ / Pd(OH)2/C / ethyl acetate / 6 h / 20 °C / atmospheric pressure

6.1: 200 mg / 2-iodoxybenzoic acid / dimethylsulfoxide / 3 h / 20 °C

7.1: 88 percent / NaClO₂; NaH₂PO₄*2H₂O; 2-methyl-2-butene / 2-methyl-propan-2-ol; H₂O / 2 h / 0 °C

8.1: 75 percent / 1-hydroxybenzotriazole hydrate; 1-(3-dimethylaminopropyl)-3-ethyl-carbodiimide hydrochloride; triethylamine / CH₂Cl₂ / 15 h / 20 °C

With sodium chlorite; sodium dihydrogenphosphate; lithium aluminium tetrahydride; n-butyllithium; 2-methyl-but-2-ene; hydrogen; (S)-[1,1']-binaphthalenyl-2,2'-diol; 1,8-diazabicyclo[5.4.0]undec-7-ene; 1-hydroxybenzotriazol-hydrate; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; N-ethyl-N,N-diisopropylamine; lithium chloride; 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione; palladium dihydroxide; In tetrahydrofuran; ethanol; hexane; dichloromethane; water; dimethyl sulfoxide; ethyl acetate; acetonitrile; tert-butyl alcohol;

DOI:10.1021/jo070560h

Reference yield:

benzyl (3S,11bR)-9,11-bis(benzyloxy)-4-oxo-2,3,4,6,7,11b-hexahydro-1H-pyrido[2,1-a]isoquinolin-3-ylcarbamate (949463-58-5) → (S)-N-((3S,11bR)-9,11-bis(benzyloxy)-4-oxo-2,3,4,6,7,11b-hexahydro-1H-pyrido[2,1-a]isoquinolin-3-yl)-16-((4S,5S)-5-decyl-2,2-dimethyl-1,3-dioxolan-4-yl)-14-(methoxymethoxy)hexadecanamide (949463-71-2)

Guidance literature:

Multi-step reaction with 5 steps

1: H₂ / Pd/C / methanol / 5 h / 20 °C / atmospheric pressure

2: methanol / 5 h / 20 °C

3: 91 percent / Cs₂CO₃; tetrabutylammonium iodide / dimethylformamide / 1 h / 0 °C

4: 96 percent / aq. HCl / ethyl acetate / 3 h / 20 °C

5: 75 percent / 1-hydroxybenzotriazole hydrate; 1-(3-dimethylaminopropyl)-3-ethyl-carbodiimide hydrochloride; triethylamine / CH₂Cl₂ / 15 h / 20 °C

With hydrogenchloride; hydrogen; tetra-(n-butyl)ammonium iodide; caesium carbonate; 1-hydroxybenzotriazol-hydrate; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; palladium on activated charcoal; In methanol; dichloromethane; ethyl acetate; N,N-dimethyl-formamide;

DOI:10.1021/jo070560h

upstream raw materials:

(S)-16-((4S,5S)-5-decyl-2,2-dimethyl-1,3-dioxolan-4-yl)-14-(methoxymethoxy)hexadecanoic acid

(3S,11bR)-3-amino-9,11-bis(benzyloxy)-2,3,6,7-tetrahydro-1H-pyrido[2,1-a]isoquinolin-4(11bH)-one

benzyl (3S,11bR)-9,11-bis(benzyloxy)-4-oxo-2,3,4,6,7,11b-hexahydro-1H-pyrido[2,1-a]isoquinolin-3-ylcarbamate

(+)-(3S,11bR)-3-(tert-butoxycarbonylamino)-9,11-dihydroxy-2,3,6,7-tetrahydro-1H-pyrido[2,1-a]isoquinolin-4(11bH)-one