gelsedine

Base Information

• Chemical Name: gelsedine
• CAS No.: 7096-96-0
• Molecular Formula: C19H24N2O3
• Molecular Weight: 328.4055
• Mol file: 7096-96-0.mol

Synonyms:gelsedine;

Chemical Property of gelsedine

Chemical Property:

• Boiling Point: 462.2°Cat760mmHg
• Flash Point: 233.3°C
• PSA: 50.80000
• Density: 1.29g/cm³
• LogP: 2.40160

Purity/Quality:

99%min ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of gelsedine

There total 4 articles about gelsedine 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: 95.0%

(-)-gelsenicine (82354-38-9) → gelsedine (7096-96-0)

Guidance literature:

With platinum(IV) oxide; hydrogen; In ethanol; at 20 ℃; for 7h; under 760.051 Torr; Inert atmosphere;

DOI:10.1021/acs.orglett.6b02263

Reference yield:

benzyl ((1S,2S,3'S,5R)-1'-methoxy-2'-oxo-8-propionyl-6-oxaspiro[bicyclo[3.2.2]non[8]ene-4,3'-indolin]-2-yl)carbamate (1341221-99-5) → gelsedine (7096-96-0)

Guidance literature:

Multi-step reaction with 2 steps

1.1: palladium diacetate; triethylamine / dichloromethane / 0.08 h / 20 °C / Inert atmosphere; Sealed tube

1.2: 0.5 h / 20 °C / Inert atmosphere; Sealed tube

1.3: 0.5 h / 20 °C / Inert atmosphere; Sealed tube

2.1: platinum(IV) oxide; hydrogen / ethanol / 7 h / 20 °C / 760.05 Torr / Inert atmosphere

With platinum(IV) oxide; hydrogen; palladium diacetate; triethylamine; In ethanol; dichloromethane;

DOI:10.1021/acs.orglett.6b02263

Reference yield:

C20H19F3N2O9S → gelsedine (7096-96-0)

Guidance literature:

Multi-step reaction with 3 steps

1: triethylsilane; N-ethyl-N,N-diisopropylamine; tetrakis(triphenylphosphine) palladium⁽⁰⁾ / N,N-dimethyl-formamide / 0.5 h / 70 °C / Inert atmosphere

2: sodium tetrahydroborate; nickel(II) chloride hexahydrate / methanol / 1 h / -78 - 20 °C / Inert atmosphere

3: platinum(IV) oxide; hydrogen / ethanol / 1 h / 20 °C / 760.05 Torr

With triethylsilane; platinum(IV) oxide; sodium tetrahydroborate; tetrakis(triphenylphosphine) palladium⁽⁰⁾; nickel(II) chloride hexahydrate; hydrogen; N-ethyl-N,N-diisopropylamine; In methanol; ethanol; N,N-dimethyl-formamide;

DOI:10.1021/jacs.8b08127

upstream raw materials:

benzyl ((1S,2S,3'S,5R)-1'-methoxy-2'-oxo-8-propionyl-6-oxaspiro[bicyclo[3.2.2]non[8]ene-4,3'-indolin]-2-yl)carbamate

(-)-gelsenicine

Downstream raw materials:

4-(toluene-4-sulfonyl)-gelsedine

Refernces

• 1、 Harada, Takaaki,Shimokawa, Jun,Fukuyama, Tohru. "Unified Total Synthesis of Five Gelsedine-Type Alkaloids: (-)-Gelsenicine, (-)-Gelsedine, (-)-Gelsedilam, (-)-14-Hydroxygelsenicine, and (-)-14,15-Dihydroxygelsenicine". . p. 4622 - 4625. Retrieved 2016/09/28.