2α,5-Epoxy-1,2-dihydro-4,5-secoakuammilan-17-oic acid methyl ester

Base Information

• Chemical Name: 2α,5-Epoxy-1,2-dihydro-4,5-secoakuammilan-17-oic acid methyl ester
• CAS No.: 3620-79-9
• Molecular Formula: C20H24N2O3
• Molecular Weight: 340.41616
• Mol file: 3620-79-9.mol

Synonyms:16-De(hydroxymethyl)aspidodasycarpine;2α,5-Epoxy-1,2-dihydro-4,5-secoakuammilan-17-oic acid methyl ester;De(hydroxymethyl)aspidodasycarpine

Chemical Property of 2α,5-Epoxy-1,2-dihydro-4,5-secoakuammilan-17-oic acid methyl ester

Chemical Property:

• PSA: 59.59000
• LogP: 2.66050

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 2α,5-Epoxy-1,2-dihydro-4,5-secoakuammilan-17-oic acid methyl ester

There total 9 articles about 2α,5-Epoxy-1,2-dihydro-4,5-secoakuammilan-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:

C26H27N3O7S → Desformo-aspidodasycarpin (3620-79-9)

Guidance literature:

With caesium carbonate; In acetonitrile; at 65 ℃; for 2h; Inert atmosphere;

DOI:10.1021/jacs.5b12880

Reference yield:

aspidodasycarpine (2744-47-0,26988-11-4) → Desformo-aspidodasycarpin (3620-79-9)

Guidance literature:

With sodium methylate; In methanol; Heating;

DOI:10.1016/S0040-4020(01)98642-9

Reference yield:

C22H28N2O8S → Desformo-aspidodasycarpin (3620-79-9)

Guidance literature:

Multi-step reaction with 7 steps

1: water; acetic acid / tetrahydrofuran / 5 h / 75 °C

2: sodium tetrahydroborate / methanol / 1.5 h / 0 °C / Inert atmosphere

3: toluene-4-sulfonic acid / benzene / 0.5 h / 80 °C / Inert atmosphere

4: Dess-Martin periodane / dichloromethane / 13 h / 40 °C / Inert atmosphere

5: trifluoroacetic acid / 1,2-dichloro-ethane / 12 h / 40 °C / Inert atmosphere

6: potassium carbonate / 1 h / 65 °C / Inert atmosphere

7: caesium carbonate / acetonitrile / 2 h / 65 °C / Inert atmosphere

With sodium tetrahydroborate; water; potassium carbonate; caesium carbonate; Dess-Martin periodane; toluene-4-sulfonic acid; acetic acid; trifluoroacetic acid; In tetrahydrofuran; methanol; dichloromethane; 1,2-dichloro-ethane; acetonitrile; benzene; 5: |Fischer Indole Synthesis;

DOI:10.1021/jacs.5b12880

upstream raw materials:

aspidodasycarpine

Refernces

• 1、 Joule,Ohashi,Gilbert,Djerassi. "Alkaloid studies. 53. The structures of nine new alkaloids from Aspidosperma dasycarpon A. DC.". . p. 1717 - 1734. Retrieved 2007/10/07.