Catharosine

Base Information

• Chemical Name: Catharosine
• CAS No.: 2564-23-0
• Molecular Formula: C₂₂H₂₈N₂O₄
• Molecular Weight: 384.475
• Mol file: 2564-23-0.mol

Synonyms:Aspidospermidine-3-carboxylicacid, 6,7-didehydro-3,4-dihydroxy-1-methyl-, methyl ester, (2b,3b,4b,5a,12b,19a)-; Catharosine (7CI,8CI)

Chemical Property of Catharosine

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of Catharosine

There total 7 articles about Catharosine 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:

tabersonine (4429-63-4) → (-)-deacetylvindorosine (2564-23-0,95044-15-8)

Guidance literature:

Multi-step reaction with 3 steps

1: 93 percent / triphenylphosphine / acetonitrile; CCl₄ / 0.5 h / 70 °C

2: m-chloroperbenzoic acid, aq. bicarbonate / CH₂Cl₂ / 0.03 h / -16 °C

3: sodium cyanoborohydride, acetic acid, sodium acetate / CH₂Cl₂; methanol / 0.17 h

With bicarbonate; sodium acetate; sodium cyanoborohydride; acetic acid; 3-chloro-benzenecarboperoxoic acid; triphenylphosphine; In methanol; tetrachloromethane; dichloromethane; acetonitrile;

DOI:10.1021/jo00379a006

Reference yield:

(-)-17-hydroxytabersonine (93771-99-4) → (-)-deacetylvindorosine (2564-23-0,95044-15-8)

Guidance literature:

Multi-step reaction with 2 steps

1: m-chloroperbenzoic acid, aq. bicarbonate / CH₂Cl₂ / 0.03 h / -16 °C

2: sodium cyanoborohydride, acetic acid, sodium acetate / CH₂Cl₂; methanol / 0.17 h

With bicarbonate; sodium acetate; sodium cyanoborohydride; acetic acid; 3-chloro-benzenecarboperoxoic acid; In methanol; dichloromethane;

DOI:10.1021/jo00379a006

Reference yield:

5-chloro-2-ethyl-(4S)-hydroxypentanal lactol (80642-07-5) → (-)-deacetylvindorosine (2564-23-0,95044-15-8)

Guidance literature:

Multi-step reaction with 5 steps

1: 1.) boric acid, 2.) triethylamine / 1.) methanol, reflux, 24 h, 2.) methanol, reflux, 12 h

2: 71 percent / triphenylphosphine / acetonitrile; CCl₄ / 0.5 h / 70 °C

3: 93 percent / triphenylphosphine / acetonitrile; CCl₄ / 0.5 h / 70 °C

4: m-chloroperbenzoic acid, aq. bicarbonate / CH₂Cl₂ / 0.03 h / -16 °C

5: sodium cyanoborohydride, acetic acid, sodium acetate / CH₂Cl₂; methanol / 0.17 h

With bicarbonate; sodium acetate; boric acid; sodium cyanoborohydride; acetic acid; triethylamine; 3-chloro-benzenecarboperoxoic acid; triphenylphosphine; In methanol; tetrachloromethane; dichloromethane; acetonitrile;

DOI:10.1021/jo00379a006

upstream raw materials:

formaldehyd

(3aR,4R,5S,10bR,12bR)-3a-Ethyl-4,5-dihydroxy-3a,4,5,11,12,12b-hexahydro-1H-6,12a-diaza-indeno[7,1-cd]fluorene-5-carboxylic acid methyl ester

tabersonine

(-)-17-hydroxytabersonine

Downstream raw materials:

(-)-vindorosine

(+/-)-vindorosine

Refernces