(5α,12R,19α)-2,3-Didehydro-6α,7α-epoxyaspidospermidine-3-carboxylic acid methyl ester

Base Information

• Chemical Name: (5α,12R,19α)-2,3-Didehydro-6α,7α-epoxyaspidospermidine-3-carboxylic acid methyl ester
• CAS No.: 72058-36-7
• Molecular Formula: C21H24N2O3
• Molecular Weight: 352.43
• Mol file: 72058-36-7.mol

Synonyms:Lochnericine;Epoxy-14,15beta-tabersonin;Epoxy-14,15β-tabersonin;

Chemical Property of (5α,12R,19α)-2,3-Didehydro-6α,7α-epoxyaspidospermidine-3-carboxylic acid methyl ester

Chemical Property:

• Vapor Pressure: 3.6E-10mmHg at 25°C
• Melting Point: 190-3°C (dec.).
• Boiling Point: 501°C at 760 mmHg
• PKA: pKa in 66% DMF: 4.2(at 25℃)
• Flash Point: 256.8°C
• PSA: 54.10000
• Density: 1.35g/cm³
• LogP: 2.50830

Purity/Quality:

98%Min ^*data from raw suppliers

Lochnericine ≥98% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Description: One of the numerous alkaloids which have been isolated from Vinca rosea L. (Syn. Catharanthus roseus G. Don.), this base yields colourless crystals from MeOH and is strongly laevorotatory with [α]D - 528° (CHCl3) or [α]27D - 432° (CHCI3). The ultraviolet spectrum of the alkaloid in EtOH shows three absorption maxima at 226, 297 and 327 ffi/.l. The suggested structure contains one methoxycarbonyl group, an imino group, a bridge ethyl group and an epoxy ring. The second nitrogen atom is tertiary.

Technology Process of (5α,12R,19α)-2,3-Didehydro-6α,7α-epoxyaspidospermidine-3-carboxylic acid methyl ester

There total 5 articles about (5α,12R,19α)-2,3-Didehydro-6α,7α-epoxyaspidospermidine-3-carboxylic 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: 69.0%

C24H25Cl3N2O5 → lochnericine (2447-58-7,72058-36-7)

Guidance literature:

With potassium dihydrogenphosphate; zinc; In tetrahydrofuran; water; at 60 ℃; for 3h;

DOI:10.1021/acs.jnatprod.0c00310

Reference yield: 35.0%

(14S,15R)-epoxy-cleavamine → lochnericine (2447-58-7,72058-36-7) + (+)-(14S,15R)-epoxy-allocatharantine

Guidance literature:

With mercury(II) diacetate; In acetic acid; at 20 ℃; for 2h;

DOI:10.1021/jo020386r

Reference yield:

(-)-tabersonine hydrochloride (29479-00-3) → lochnericine (2447-58-7,72058-36-7) + (14,15)α-epoxy-11-methoxytabersonine (22223-16-1,22255-04-5)

Guidance literature:

Yield given. Yields of byproduct given; biotransformation in cell suspension cultures of Catharanthus roseus;

DOI:10.1016/0031-9422(92)83447-7

upstream raw materials:

(-)-tabersonine hydrochloride

tabersonine

Refernces

• 1、 Eles, Janos,Kalaus, Gyoergy,Greiner, Istvan,Kajtar-Peredy, Maria,Szabo, Pal,Keseru, Gyoergy Miklos,Szabo, Lajos,Szantay, Csaba. "Synthesis of vinca alkaloids and related compounds. 100. Stereoselective oxidation reactions of compounds with the aspidospermane and quebrachamine ring system. First synthesis of some alkaloids containing the epoxy ring". . p. 7255 - 7260. Retrieved 2007/10/03.