Methyl 3beta-hydroxy-20-oxo-30-norlupan-28-oate

Base Information

• Chemical Name: Methyl 3beta-hydroxy-20-oxo-30-norlupan-28-oate
• CAS No.: 4356-32-5
• Molecular Formula: C30H48O4
• Molecular Weight: 472.709
• European Community (EC) Number: 224-430-5
• DSSTox Substance ID: DTXSID00963045
• Nikkaji Number: J205.734D
• Wikidata: Q82944852
• ChEMBL ID: CHEMBL3325723
• Mol file: 4356-32-5.mol

Synonyms:4356-32-5;EINECS 224-430-5;CHEMBL3325723;Methyl 3beta-hydroxy-20-oxo-30-norlupan-28-oate;DTXSID00963045;BDBM50058819;methyl-3beta-hydroxy-20-oxo-30-norlupan-28-oate;3beta-Hydroxy-20-oxo-30-norlupan-28-oic acid methyl ester;Methyl 1-acetyl-9-hydroxy-5a,5b,8,8,11a-pentamethylicosahydro-3aH-cyclopenta[a]chrysene-3a-carboxylate

Chemical Property of Methyl 3beta-hydroxy-20-oxo-30-norlupan-28-oate

Chemical Property:

• Boiling Point: 539.2±25.0 °C(Predicted)
• PKA: 15.15±0.70(Predicted)
• PSA: 63.60000
• Density: 1.074±0.06 g/cm3(Predicted)
• LogP: 6.19080
• XLogP3: 6.5
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 3
• Exact Mass: 472.35526001
• Heavy Atom Count: 34
• Complexity: 879

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(=O)C1CCC2(C1C3CCC4C5(CCC(C(C5CCC4(C3(CC2)C)C)(C)C)O)C)C(=O)OC
• Isomeric SMILES: CC(=O)[C@@H]1CC[C@]2([C@H]1[C@H]3CC[C@@H]4[C@]5(CC[C@@H](C([C@@H]5CC[C@]4([C@@]3(CC2)C)C)(C)C)O)C)C(=O)OC

Technology Process of Methyl 3beta-hydroxy-20-oxo-30-norlupan-28-oate

There total 9 articles about Methyl 3beta-hydroxy-20-oxo-30-norlupan-28-oate 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: 89.0%

platanic acid (6060-06-6) + methyl iodide (74-88-4) → methyl (3β)-3-hydroxy-20-oxo-30-norlupan-28-oate (4356-32-5)

Guidance literature:

platanic acid; With potassium carbonate; In N,N-dimethyl-formamide; at 20 ℃; for 0.166667h;

methyl iodide; In N,N-dimethyl-formamide; at 25 ℃; for 0.5h;

DOI:10.1016/j.ejmech.2017.11.046

Reference yield: 58.0%

methyl betulinate (2259-06-5,25493-95-2) → methyl (3β)-3-hydroxy-20-oxo-30-norlupan-28-oate (4356-32-5)

Guidance literature:

methyl betulinate; With ozone; In methanol; dichloromethane; at -78 ℃;

With triethyl phosphite; In methanol; dichloromethane; at -78 - 20 ℃; Inert atmosphere;

Reference yield:

Betulinic acid (472-15-1) → methyl (3β)-3-hydroxy-20-oxo-30-norlupan-28-oate (4356-32-5)

Guidance literature:

Multi-step reaction with 2 steps

1: O₃ / CHCl₃ / Ambient temperature

2: 5 mg / diethyl ether

With ozone; In diethyl ether; chloroform;

DOI:10.1002/ardp.19963291005

upstream raw materials:

Acetylmethylbetulinate

methyl 3β-acetoxy-20-oxo-30-norlupane-28-carboxylate

diazomethane

platanic acid

Refernces

• 1、 Kahnt, Michael,Heller, Lucie,Grabandt, Patricia,Al-Harrasi, Ahmed,Csuk, René. "Platanic acid: A new scaffold for the synthesis of cytotoxic agents". . p. 259 - 265. Retrieved 2017/12/07.