20S,24R-Epoxydammar-12,25-diol-3-one

Base Information

• Chemical Name: 20S,24R-Epoxydammar-12,25-diol-3-one
• CAS No.: 25279-15-6
• Molecular Formula: C₃₀H₅₀O₄
• Molecular Weight: 474.725
• UNII: RCA3293YRJ
• ChEMBL ID: CHEMBL2426028
• Nikkaji Number: J129.884D
• Mol file: 25279-15-6.mol

Synonyms:3-Dehydropyxinol;25279-15-6;RCA3293YRJ;20S,24R-Epoxydammar-12,25-diol-3-one;UNII-RCA3293YRJ;(20S)-Protopanaxadiol metabolite M2-2;(20S,24R)-12beta,25-Dihydroxy-20,24-epoxydammaran-3-one;(12beta,24R)-20,24-Epoxy-12,25-dihydroxydammaran-3-one;Dammaran-3-one, 20,24-epoxy-12,25-dihydroxy-, (12beta,20S,24R)-;20S,24R-Epoxydammara-12beta,25-diol-3-one;CHEMBL2426028;(5R,8R,9R,10R,12R,13R,14R,17S)-12-hydroxy-17-[(2S,5R)-5-(2-hydroxypropan-2-yl)-2-methyloxolan-2-yl]-4,4,8,10,14-pentamethyl-1,2,5,6,7,9,11,12,13,15,16,17-dodecahydrocyclopenta[a]phenanthren-3-one;AKOS027250676;FS-9658;(20S,24R)-12|A,25-Dihydroxy-20,24-epoxydammarane-3-one;(12.BETA.,24R)-20,24-EPOXY-12,25-DIHYDROXYDAMMARAN-3-ONE;(20S,24R)-12.BETA.,25-DIHYDROXY-20,24-EPOXYDAMMARAN-3-ONE;DAMMARAN-3-ONE, 20,24-EPOXY-12,25-DIHYDROXY-, (12.BETA.,20S,24R)-;(5R, 8R, 9R, 10R, 12R, 13R, 14R, 17S)-12-hydroxy-17-[(2S, 5R)-5-(2-hydroxypropan-2-yl)-2-methyloxolan-2-yl]-4, 4, 8, 10, 14-pentamethyl-1, 2, 5, 6, 7, 9, 11, 12, 13, 15, 16, 17-dodecahydrocyclopenta[a]phenanthren-3-one

Chemical Property of 20S,24R-Epoxydammar-12,25-diol-3-one

Chemical Property:

• PSA: 66.76000
• LogP: 5.92000
• XLogP3: 5.6
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 2
• Exact Mass: 474.37091007
• Heavy Atom Count: 34
• Complexity: 864

Purity/Quality:

98%min ^*data from raw suppliers

Dammaran-3-one,20,24-epoxy-12,25-dihydroxy-,(12β,24R)- 95+% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1(C2CCC3(C(C2(CCC1=O)C)CC(C4C3(CCC4C5(CCC(O5)C(C)(C)O)C)C)O)C)C
• Isomeric SMILES: C[C@]1(CC[C@@H](O1)C(C)(C)O)[C@H]2CC[C@@]3([C@@H]2[C@@H](C[C@H]4[C@]3(CC[C@@H]5[C@@]4(CCC(=O)C5(C)C)C)C)O)C

Technology Process of 20S,24R-Epoxydammar-12,25-diol-3-one

There total 8 articles about 20S,24R-Epoxydammar-12,25-diol-3-one 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: 84.0%

(20S,24R)-epoxydammarane–3β,12β,25-triol (162062-88-6) → (20S,24R)-epoxydammarane–12β,25-diol-3-one (25279-15-6)

Guidance literature:

With pyridinium chlorochromate; In dichloromethane; at 20 ℃; for 15h; Cooling with ice;

Reference yield:

protopanaxadiol (6892-79-1,7755-01-3,30636-90-9,38243-15-1,53368-76-6,103834-30-6) → (20S,24R)-epoxydammarane–12β,25-diol-3-one (25279-15-6)

Guidance literature:

Multi-step reaction with 4 steps

1: dmap; pyridine / 24 h / 20 °C

2: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 2 h / -3 °C

3: potassium hydroxide; methanol / 2 h / Reflux

4: pyridinium chlorochromate / dichloromethane / 3 h / 20 °C

With pyridine; methanol; dmap; 3-chloro-benzenecarboperoxoic acid; pyridinium chlorochromate; potassium hydroxide; In dichloromethane;

DOI:10.1016/j.ejmech.2013.07.041

Reference yield:

3,12-di-O-acetydammar-24-ene-3β,12β,20(S)-triol (7755-02-4) → (20S,24R)-epoxydammarane–12β,25-diol-3-one (25279-15-6)

Guidance literature:

Multi-step reaction with 3 steps

1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 2 h / -3 °C

2: potassium hydroxide; methanol / 2 h / Reflux

3: pyridinium chlorochromate / dichloromethane / 3 h / 20 °C

With methanol; 3-chloro-benzenecarboperoxoic acid; pyridinium chlorochromate; potassium hydroxide; In dichloromethane;

DOI:10.1016/j.ejmech.2013.07.041

upstream raw materials:

Betulafolienetriol oxide

(5R,8R,9R,10R,12R,13R,14R,17S)-17-[(2S,5R)-5-(1-Hydroxy-1-methyl-ethyl)-2-methyl-tetrahydro-furan-2-yl]-4,4,8,10,14-pentamethyl-hexadecahydro-cyclopenta[a]phenanthrene-3,12-diol

3,12-di-O-acetydammar-24-ene-3β,12β,20(S)-triol

(20S,24)-epoxy-3β,12β-O-diacetyldammarane-25-ol

Downstream raw materials:

20(S),24(R)-Epoxydammarane-3β,12β,25-triol

Refernces

• 1、 Ren, Qianwen,Yang, Gangqiang,Guo, Mengqi,Guo, Jingwen,Li, Yang,Lu, Jing,Yang, Qing,Tang, Hanhan,Li, Yi,Fang, Xiaojuan,Sun, Yixiao,Qi, Jia Grace,Tian, Jingwei,Wang, Hongbo. "Design, synthesis, and discovery of ocotillol-type amide derivatives as orally available modulators of P-glycoprotein-mediated multidrug resistance". . p. 118 - 130. Retrieved 2019.
• 2、 Shao, Xiao,Zhang, Shengyu,Zhou, Yunyun,Zeng, Xianming,Zhou, Zhiwen. "Design, synthesis and biological evaluation of novel ocotillol-type triterpenoid derivatives as antibacterial agents". . p. 27 - 38. Retrieved 2020/03/17.