(16S)-Curan-17-oic acid methyl ester

Base Information

• Chemical Name: (16S)-Curan-17-oic acid methyl ester
• CAS No.: 7267-97-2
• Molecular Formula: C₂₀H₂₆N₂O₂
• Molecular Weight: 326.439
• Mol file: 7267-97-2.mol

Synonyms:curan-17-oic acid methyl ester

Chemical Property of (16S)-Curan-17-oic acid methyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (16S)-Curan-17-oic acid methyl ester

There total 13 articles about (16S)-Curan-17-oic acid methyl ester 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:

(-)-19,20-dihydroakuammicine (2912-08-5) → Methyl-2β,16α,20α-curanoat (7267-97-2,52437-06-6,112708-67-5,115267-73-7,146726-44-5) + curan-17-oic acid methyl ester (7267-97-2)

Guidance literature:

With sodium cyanoborohydride; In acetic acid; at 10 ℃; for 2h; Overall yield = 79 %; Overall yield = 442 mg; Inert atmosphere;

DOI:10.1002/anie.201505198

Reference yield:

(-)-19,20-dihydroakuammicine (2912-08-5) → Methyl-2β,16α,20α-curanoat (7267-97-2,52437-06-6,112708-67-5,115267-73-7,146726-44-5) + curan-17-oic acid methyl ester (7267-97-2)

Guidance literature:

With sodium cyanoborohydride; In acetic acid; at 10 ℃; for 2h; Overall yield = 79 %; Overall yield = 442 mg; Inert atmosphere;

DOI:10.1002/anie.201505198

Reference yield:

C16H18N2O2 (1322613-98-8) → Methyl-2β,16α,20α-curanoat (7267-97-2,52437-06-6,112708-67-5,115267-73-7,146726-44-5) + curan-17-oic acid methyl ester (7267-97-2)

Guidance literature:

Multi-step reaction with 4 steps

1.1: potassium carbonate / acetonitrile / 0.17 h / -10 °C / Inert atmosphere

1.2: 14 h / -10 - 20 °C / Inert atmosphere

2.1: palladium diacetate; triphenylphosphine; triethylamine / 3.5 h / 90 °C / Inert atmosphere

3.1: platinum(IV) oxide; hydrogen / methanol / 24 h / 20 °C / Inert atmosphere

4.1: sodium cyanoborohydride / acetic acid / 2 h / 10 °C / Inert atmosphere

With platinum(IV) oxide; hydrogen; palladium diacetate; sodium cyanoborohydride; potassium carbonate; triethylamine; triphenylphosphine; In methanol; acetic acid; acetonitrile; 2.1: |Heck Reaction;

DOI:10.1002/anie.201505198

upstream raw materials:

C₁₆H₁₈N₂O₂

(-)-akuammicine

(-)-19,20-dihydroakuammicine

Downstream raw materials:

(-)-leucoridine C

(+)-geissoschizoline

Refernces