Methyl acetyl betulinate

Base Information

• Chemical Name: Methyl acetyl betulinate
• CAS No.: 4356-30-3
• Deprecated CAS: 500218-48-4
• Molecular Formula: C₃₃H₅₂O₄
• Molecular Weight: 512.773
• DSSTox Substance ID: DTXSID40963044
• Nikkaji Number: J1.401.838G
• Wikidata: Q82944851
• Metabolomics Workbench ID: 140688
• ChEMBL ID: CHEMBL508907
• Mol file: 4356-30-3.mol

Synonyms:Methyl acetyl betulinate;4356-30-3;Methyl acetylbetulate;Methyl (3-O-acetyl)betulinate;Lup-20(29)-en-28-oic acid, 3-(acetyloxy)-, methyl ester, (3beta)-;Methyl 3-(acetyloxy)lup-20(29)-en-28-oate (3beta)-;C33H52O4;C33-H52-O4;Acetyl methyl betulinate;methyl (1R,3aS,5aR,5bR,7aR,9S,11aR,11bR,13aR,13bR)-9-acetyloxy-5a,5b,8,8,11a-pentamethyl-1-prop-1-en-2-yl-1,2,3,4,5,6,7,7a,9,10,11,11b,12,13,13a,13b-hexadecahydrocyclopenta[a]chrysene-3a-carboxylate;CHEMBL508907;SCHEMBL3784133;DTXSID40963044;AKOS040753025;Methyl 3-(acetyloxy)lup-20(29)-en-28-oate

Chemical Property of Methyl acetyl betulinate

Chemical Property:

• Vapor Pressure: 1.35E-11mmHg at 25°C
• Melting Point: 201-203 °C
• Boiling Point: 536.8°Cat760mmHg
• Flash Point: 252.7°C
• PSA: 52.60000
• Density: 1.06g/cm³
• LogP: 7.74870
• XLogP3: 9.1
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 5
• Exact Mass: 512.38656014
• Heavy Atom Count: 37
• Complexity: 983

Purity/Quality:

99% ^*data from raw suppliers

3-ACETYLOXY-(3-BETA)-LUP-20(29)-EN-28-OIC ACID METHYL ESTER 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(=C)C1CCC2(C1C3CCC4C5(CCC(C(C5CCC4(C3(CC2)C)C)(C)C)OC(=O)C)C)C(=O)OC
• Isomeric SMILES: CC(=C)[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)OC(=O)C)C)C(=O)OC

Technology Process of Methyl acetyl betulinate

There total 22 articles about Methyl acetyl betulinate 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: 92.0%

methyl betulinate (2259-06-5,25493-95-2) + acetic anhydride (108-24-7) → Acetylmethylbetulinate (4356-30-3,25488-52-2)

Guidance literature:

With dmap; triethylamine; In dichloromethane; at 20 ℃;

Reference yield: 59.0%

3-O-acetylbetulinic acid (10376-50-8,38736-81-1) + methyl iodide (74-88-4) → Acetylmethylbetulinate (4356-30-3,25488-52-2)

Guidance literature:

With potassium carbonate; In dichloromethane; at 55 ℃; for 48h; Inert atmosphere;

DOI:10.1016/j.bmcl.2017.12.060

Reference yield:

Betulinic acid (472-15-1) → Acetylmethylbetulinate (4356-30-3,25488-52-2)

Guidance literature:

Multi-step reaction with 2 steps

1: 87 percent / diethyl ether; CHCl₃

2: 86 percent / pyridine / 6 h

With pyridine; In diethyl ether; chloroform;

DOI:10.1021/np049938m

upstream raw materials:

diazomethane

3-O-acetylbetulinic acid

methyl betulinate

acetic anhydride

Downstream raw materials:

methyl (3β)-3-hydroxy-20-oxo-30-norlupan-28-oate

Acetyl-dihydrobetulinsaeure-methylester

diospyrolide

Refernces

• 1、 -. "COMPOUNDS FOR REDUCING GLUCOCORTICOIDS, AND METHODS OF TREATMENT THEREOF". Paragraph 0138-0140. . Retrieved 2014/05/24.
• 2、 Uzenkova,Petrenko,Shakirov,Shul ts,Tolstikov. "Synthesis of 30-amino derivatives of lupane triterpenoids". . p. 692 - 700. Retrieved 2008/02/03.