(2β,5α,12β,19α)-4β-(Acetyloxy)-6,7-didehydro-3β-hydroxy-1-methylaspidospermidine-3-carboxylic acid methyl ester

Base Information

• Chemical Name: (2β,5α,12β,19α)-4β-(Acetyloxy)-6,7-didehydro-3β-hydroxy-1-methylaspidospermidine-3-carboxylic acid methyl ester
• CAS No.: 5231-60-7
• Molecular Formula: C24H30N2O5
• Molecular Weight: 426.5054
• Mol file: 5231-60-7.mol

Synonyms:Aspidospermidine-3-carboxylic acid, 4-(acetyloxy)-6,7-didehydro-3-hydroxy-1-methyl-, methyl ester, (2beta,3beta,4beta,5alpha,12beta,19alpha)- (9CI);Vindolidin;1H-Indolizino(8,1-cd)carbazole-5-carboxylic acid, 3a-ethyl-3a,4,5,5a,6,11,12,13a-octahydro-4,5-dihydroxy-6-methyl-, methyl ester, 4-acetate;1H-INDOLIZINO(8,1-cd)CARBAZOLE-5-CARBOXYLIC ACID, 3a-ETHYL-3a,4,5,5a,6,11,12,13a;Vindolidine;Vindorosine;1H-Indolizino(8,1-cd)carbazole-5-carboxylic acid, 3a-ethyl-3a,4,5, 5a,6,11,12,13a-octahydro-4,5-dihydroxy-6-methyl-, methyl ester, 4-acetate;Aspidospermidine-3-carboxylic acid,4-(acetyloxy)-6,7-didehydro-3-hydroxy- 1-methyl-,methyl ester,(2a,3a,4a,5R,12a,19R)-;Aspidospermidine-3-carboxylic acid, 4- (acetyloxy)-6, 7-didehydro-3-hydroxy-1-methyl-, methyl ester, (2.beta.,3.beta., 4.beta.,5.alpha.,12.beta.,19.alpha.)-;

Chemical Property of (2β,5α,12β,19α)-4β-(Acetyloxy)-6,7-didehydro-3β-hydroxy-1-methylaspidospermidine-3-carboxylic acid methyl ester

Chemical Property:

• Vapor Pressure: 3.49E-12mmHg at 25°C
• Melting Point: 167°
• Refractive Index: 1.634
• Boiling Point: 532.821 °C at 760 mmHg
• Flash Point: 276.041 °C
• PSA: 79.31000
• Density: 1.33g/cm³
• LogP: 1.63560

Purity/Quality:

99% ^*data from raw suppliers

Vindorosine 95+% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Description: An imidazolidinocarbazole alkaloid present in Vinca rosea L., the base is best crystallized from a mixture of C6H6 and light petroleum. It yields colourless needles and has [α]16D - 31 ° (CHCl3). The ultraviolet spectrum consists of two absorption maxima occurring at 250 and 302 mμ.

Technology Process of (2β,5α,12β,19α)-4β-(Acetyloxy)-6,7-didehydro-3β-hydroxy-1-methylaspidospermidine-3-carboxylic acid methyl ester

There total 9 articles about (2β,5α,12β,19α)-4β-(Acetyloxy)-6,7-didehydro-3β-hydroxy-1-methylaspidospermidine-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: 99.0%

(-)-deacetylvindorosine (2564-23-0,95044-15-8) + acetyl chloride (75-36-5) → (-)-vindorosine (5231-60-7,33190-27-1)

Guidance literature:

With dmap; triethylamine; In dichloromethane; for 6h; Ambient temperature;

DOI:10.1021/jo00379a006

Reference yield:

tabersonine (4429-63-4) → (-)-vindorosine (5231-60-7,33190-27-1)

Guidance literature:

Multi-step reaction with 4 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

4: 99 percent / 4-(dimethylamino)pyridine, triethylamine / CH₂Cl₂ / 6 h / Ambient temperature

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

DOI:10.1021/jo00379a006

Reference yield:

(-)-17-hydroxytabersonine (93771-99-4) → (-)-vindorosine (5231-60-7,33190-27-1)

Guidance literature:

Multi-step reaction with 3 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

3: 99 percent / 4-(dimethylamino)pyridine, triethylamine / CH₂Cl₂ / 6 h / Ambient temperature

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

DOI:10.1021/jo00379a006

upstream raw materials:

(-)-deacetylvindorosine

acetyl chloride

tabersonine

(-)-17-hydroxytabersonine

Refernces

• 1、 Andriamialisoa, Ratremaniaina Zo,Langlois, Nicole,Langlois, Yves. "A New Efficient Total Synthesis of Vindorosine and Vindoline". . p. 961 - 967. Retrieved 2007/10/02.