(+)-Erythristemine

Base Information

• Chemical Name: (+)-Erythristemine
• CAS No.: 28619-41-2
• Molecular Formula: C₂₀H₂₅NO₄
• Molecular Weight: 343.423
• Mol file: 28619-41-2.mol

Synonyms:Erythristemine(8CI); 1H-Indolo[7a,1-a]isoquinoline, erythrinan deriv.; Erythristemin

Chemical Property of (+)-Erythristemine

Chemical Property:

• PSA: 40.16000
• LogP: 2.75500

Purity/Quality:

98%min ^*data from raw suppliers

Erythristemine ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of (+)-Erythristemine

There total 14 articles about (+)-Erythristemine 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: 78.9%

O-methyl-erythrartine-N-oxide (80153-98-6) → erythristemine (28619-41-2,125145-53-1)

Guidance literature:

With triethyl phosphite; In benzene; for 1h; Heating;

Reference yield: 73.0%

(+/-)-11β-methoxyerysotramidine (125145-68-8,136945-72-7) → (+/-)-erythristemine (28619-41-2,125145-53-1)

Guidance literature:

With lithium aluminium tetrahydride; aluminium trichloride;

DOI:10.1039/P19890001357

Reference yield:

(4aR,9R,13bS)-9,11,12-Trimethoxy-4a,5,8,9-tetrahydro-indolo[7a,1-a]isoquinoline-2,6-dione (125145-65-5) → (+/-)-erythristemine (28619-41-2,125145-53-1)

Guidance literature:

Multi-step reaction with 4 steps

1: 57 percent / NaBH₄, CeCl₃*7H₂O / methanol / 0.33 h / 0 °C

2: 1.) NaH, imidazole, 2.) n-Bu₄NHSO₄ / 1.) THF, 50 deg C, 50 min, 2.) THF, 60 deg C, 2 h

3: 1.) lithium diisopropylamide, 2.) diphenyldiselenide, 3.) NaIO₄

4: 73 percent / LiAlH₄, AlCl₃ / diethyl ether; tetrahydrofuran / 0.5 h / 0 °C

With 1H-imidazole; sodium tetrahydroborate; sodium periodate; lithium aluminium tetrahydride; aluminium trichloride; cerium(III) chloride; diphenyl diselenide; tetra(n-butyl)ammonium hydrogensulfate; sodium hydride; lithium diisopropyl amide; In tetrahydrofuran; methanol; diethyl ether;

DOI:10.1248/cpb.42.197

upstream raw materials:

(+/-)-11β-methoxyerysotramidine

3α,15,16-Trimethoxy-8-oxo-Δ¹-cis-erythrinan

(+/-)-3α,15,16-trimethoxy-8-oxo-Δ^1,6-erythrinan

(4aR,9R,13bS)-9,11,12-Trimethoxy-4a,5,8,9-tetrahydro-indolo[7a,1-a]isoquinoline-2,6-dione

Refernces

• 1、 Chawla, Amrik Singh,Sood, Ashwani,Kumar, Manoj,Jackson, Anthony H.. "ALKALOID CONSTITUENTS FROM ERYTHRINA XBIDWILLII FLOWERS". . p. 372 - 374. Retrieved 2007/10/02.
• 2、 Saragiotto,Leitao Filho,Marsaioli. "Erysotrine-N-oxide and erythrartine-N-oxide, two novel alkaloids from Erythrina mulungu". . p. 2771 - 2775. Retrieved 2007/10/02.