10-O-Acetyl SN-38

Base Information

• Chemical Name: 10-O-Acetyl SN-38
• CAS No.: 946821-59-6
• Molecular Formula: C₂₄H₂₂N₂O₆
• Molecular Weight: 434.448
• Mol file: 946821-59-6.mol

Synonyms:(4S)-9-(Acetyloxy)-4,11-diethyl-4-hydroxy-1H-pyrano[3',4':6,7]indolizino[1,2-b]quinoline-3,14(4H,12H)-dione;10-Acetyloxy-7-ethylcamptothecin;10-Hydroxy-7-ethylcamptothecin 10-Acetate;

Chemical Property of 10-O-Acetyl SN-38

Chemical Property:

• Boiling Point: 793.3±60.0 °C(Predicted)
• PKA: 11.21±0.20(Predicted)
• PSA: 107.72000
• Density: 1.46±0.1 g/cm3(Predicted)
• LogP: 2.56730
• Storage Temp.: -20°C Freezer, Under inert atmosphere
• Solubility.: DMSO (Slightly, Heated)

Purity/Quality:

99% ^*data from raw suppliers

10-O-AcetylSN-38 ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of 10-O-Acetyl SN-38

There total 3 articles about 10-O-Acetyl SN-38 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: 39.0%

7-ethyl-10-hydroxycamptothecin (86639-52-3,110714-48-2,130144-34-2,113015-38-6,647852-82-2) + acetyl chloride (75-36-5) → (S)-4,11-Diethyl-4-hydroxy-3,14-dioxo-3,4,12,14-tetrahydro-1H-pyrano[3′,4’:6,7]indolizino[1,2-b]-quinolin-9-yl acetate (946821-59-6)

Guidance literature:

With dmap; triethylamine; In dichloromethane; at 0 - 25 ℃; for 16h; Inert atmosphere;

DOI:10.1246/bcsj.20150405

Reference yield:

7-ethyl-10-hydroxycamptothecin (86639-52-3,110714-48-2,130144-34-2,113015-38-6,647852-82-2) → (S)-4,11-Diethyl-4-hydroxy-3,14-dioxo-3,4,12,14-tetrahydro-1H-pyrano[3′,4’:6,7]indolizino[1,2-b]-quinolin-9-yl acetate (946821-59-6)

Guidance literature:

With dmap; triethylamine; acetyl chloride; In dichloromethane; at 0 - 20 ℃; for 16h;

DOI:10.1021/acs.molpharmaceut.8b00477

Reference yield:

7-ethyl-10-hydroxycamptothecin (86639-52-3,110714-48-2,130144-34-2,113015-38-6,647852-82-2) + acetic acid (64-19-7,77671-22-8) → (S)-4,11-Diethyl-4-hydroxy-3,14-dioxo-3,4,12,14-tetrahydro-1H-pyrano[3′,4’:6,7]indolizino[1,2-b]-quinolin-9-yl acetate (946821-59-6)

Guidance literature:

With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In dichloromethane;

DOI:10.1246/bcsj.20190088

upstream raw materials:

7-ethyl-10-hydroxycamptothecin

acetyl chloride

acetic acid

Refernces

• 1、 Koseki, Yoshitaka,Ikuta, Yoshikazu,Kamishima, Takaaki,Onodera, Tsunenobu,Oikawa, Hidetoshi,Kasai, Hitoshi. "Drug release is determined by the chain length of fatty acid-conjugated anticancer agent as one component of nano-prodrug". . p. 540 - 545. Retrieved 2016.
• 2、 -. "CAMPTOTHECIN CONJUGATES". Paragraph 0788-0789; 0848-0849. . Retrieved 2019/12/28.