lycopsamine N-oxide

Base Information

• Chemical Name: lycopsamine N-oxide
• CAS No.: 95462-15-0
• Molecular Formula: C₁₅H₂₅NO₆
• Molecular Weight: 315.367
• Mol file: 95462-15-0.mol

Synonyms:Butanoicacid, 2,3-dihydroxy-2-(1-methylethyl)-,(2,3,5,7a-tetrahydro-1-hydroxy-1H-pyrrolizin-7-yl)methyl ester, N-oxide, [1R-[1a,7(2S*,3S*),7ab]]-; Butanoic acid,2,3-dihydroxy-2-(1-methylethyl)-,[(1R,7aR)-2,3,5,7a-tetrahydro-1-hydroxy-4-oxido-1H-pyrrolizin-7-yl]methylester, (2S,3S)- (9CI); Lycopsamine N-oxide

Chemical Property of lycopsamine N-oxide

Chemical Property:

• PKA: 12.54±0.29(Predicted)
• PSA: 116.42000
• LogP: -0.35590
• Storage Temp.: -20°C
• Solubility.: Chloroform (Slightly), Methanol (Slightly)

Purity/Quality:

98%,99%, ^*data from raw suppliers

(+)-LycopsamineN-Oxide ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Uses: (+)-Lycopsamine N-Oxide, is occurs in pyrrolizidine alkaloid-containing plants, which are the most common poisonous plants affecting livestock, wildlife, and humans. Thye are being known as hepatotoxins and tumorigens.

Technology Process of lycopsamine N-oxide

There total 6 articles about lycopsamine N-oxide 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: 85.0%

lycopsamine (10285-07-1,26131-12-4) → lycopsamine N-oxide (95462-15-0)

Guidance literature:

With dihydrogen peroxide; In ethanol; water; at 20 ℃; for 168h;

DOI:10.1002/pca.2511

Reference yield:

(2S,3S)-2,3-dihydroxy-2-(1-methylethyl)butyric acid (17132-48-8) → lycopsamine N-oxide (95462-15-0)

Guidance literature:

Multi-step reaction with 4 steps

1: conc. aq. HCl / 1.5 h / 25 °C

2: 1.) N,N'-carbonyldiimidazole (CDI), 2.) imidazoylsodium / 1.) DMF, 15 min, 2.) DMF, 25 deg C, 24 h

3: 0.6 N aq. HCl / 24 h / 25 °C

4: m-chloroperbenzoic acid / CHCl₃ / 0.33 h / Ambient temperature

With hydrogenchloride; imidazolyl sodium; 3-chloro-benzenecarboperoxoic acid; 1,1'-carbonyldiimidazole; In chloroform;

DOI:10.1021/jm00383a001

Reference yield:

(+/-)-trachelanthic acid (17132-45-5) → lycopsamine N-oxide (95462-15-0)

Guidance literature:

Multi-step reaction with 5 steps

2: conc. aq. HCl / 1.5 h / 25 °C

3: 1.) N,N'-carbonyldiimidazole (CDI), 2.) imidazoylsodium / 1.) DMF, 15 min, 2.) DMF, 25 deg C, 24 h

4: 0.6 N aq. HCl / 24 h / 25 °C

5: m-chloroperbenzoic acid / CHCl₃ / 0.33 h / Ambient temperature

With hydrogenchloride; imidazolyl sodium; 3-chloro-benzenecarboperoxoic acid; 1,1'-carbonyldiimidazole; In chloroform;

DOI:10.1021/jm00383a001

upstream raw materials:

lycopsamine

(2S,3S)-2,3-dihydroxy-2-(1-methylethyl)butyric acid

(+/-)-trachelanthic acid

(4S,5S)-4-Isopropyl-2,2,5-trimethyl-[1,3]dioxolane-4-carboxylic acid (7R,7aR)-7-hydroxy-5,6,7,7a-tetrahydro-3H-pyrrolizin-1-ylmethyl ester

Downstream raw materials:

lycopsamine A

Refernces

• 1、 Ruan, Jianqing,Li, Na,Xia, Qingsu,Fu, Peter P.,Peng, Shuying,Ye, Yang,Lin, Ge. "Characteristic ion clusters as determinants for the identification of pyrrolizidine alkaloid N-oxides in pyrrolizidine alkaloid-containing natural products using HPLC-MS analysis". body text. p. 331 - 337. Retrieved 2012/06/15.