CID 5195969

Base Information

• Chemical Name: CID 5195969
• CAS No.: 82508-32-5
• Molecular Formula: C₂₂H₂₈O₆
• Molecular Weight: 388.461
• European Community (EC) Number: 683-228-9
• Wikidata: Q105013942
• Mol file: 82508-32-5.mol

Synonyms:pseudolaric acid A

Chemical Property of CID 5195969

Chemical Property:

• Vapor Pressure: 1.5E-14mmHg at 25°C
• Melting Point: 206-207℃
• Refractive Index: 1.4450 (estimate)
• Boiling Point: 571.5°Cat760mmHg
• PKA: 4.52±0.19(Predicted)
• Flash Point: 196.6°C
• PSA: 89.90000
• Density: 1.23g/cm³
• LogP: 3.71750
• XLogP3: 2.7
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 5
• Exact Mass: 388.18858861
• Heavy Atom Count: 28
• Complexity: 806

Purity/Quality:

98%,99%, ^*data from raw suppliers

Pseudolaric Acid A ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1=CCC23CCC(C2(CC1)OC(=O)C)C(OC3=O)(C)C=CC=C(C)C(=O)O
• Uses: Pseudolaric Acid A is a cytotoxic natural product and a potential antitumor drug.

Technology Process of CID 5195969

There total 30 articles about CID 5195969 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: 90.0%

C24H34O7 + acetic anhydride (108-24-7) → pseudolaric acid A (82508-32-5)

Guidance literature:

With toluene-4-sulfonic acid; at 20 ℃; Inert atmosphere;

DOI:10.1021/ol200741j

Reference yield:

4-(diethoxy-phosphoryl)-2-methyl-but-2-enoic acid 2-methoxy-ethoxymethyl ester → pseudolaric acid A (82508-32-5)

Guidance literature:

Multi-step reaction with 5 steps

1: n-BuLi / tetrahydrofuran; hexane / 0 - 20 °C

2: aq. AcOH / 0.5 h / 60 °C

3: Dess-Martin periodinane / CH₂Cl₂ / 1 h / 20 °C

4: aq. HCl / tetrahydrofuran / 7 h / 20 °C

5: DMAP / 8 h / 20 °C

With hydrogenchloride; dmap; n-butyllithium; Dess-Martin periodane; acetic acid; In tetrahydrofuran; hexane; dichloromethane; 1: Horner-Emmons reaction / 3: Dess-Martin oxidation;

DOI:10.1002/anie.200602056

Reference yield:

7-hydroxy-11-methoxy-4,9-dimethyl-10-oxa-tricyclo[6.3.2.01,7]tridec-3-ene-9-carbaldehyde → pseudolaric acid A (82508-32-5)

Guidance literature:

Multi-step reaction with 5 steps

1: n-BuLi / tetrahydrofuran; hexane / 0 - 20 °C

2: aq. AcOH / 0.5 h / 60 °C

3: Dess-Martin periodinane / CH₂Cl₂ / 1 h / 20 °C

4: aq. HCl / tetrahydrofuran / 7 h / 20 °C

5: DMAP / 8 h / 20 °C

With hydrogenchloride; dmap; n-butyllithium; Dess-Martin periodane; acetic acid; In tetrahydrofuran; hexane; dichloromethane; 1: Horner-Emmons reaction / 3: Dess-Martin oxidation;

DOI:10.1002/anie.200602056

upstream raw materials:

acetyl chloride

deacetylpseudolaric acid A

1-(2,2-diethyl-4-methyl-[1,3]dioxolan-4-yl)-8a-hydroxy-6-methyl-2,3,4,7,8,8a-hexahydro-1H-azulene-3a-carbaldehyde

3-(2,2-diethyl-4-methyl-[1,3]dioxolan-4-yl)-8a-hydroxymethyl-6-methyl-2,3,4,5,8,8a-hexahydro-1H-azulen-3a-ol

Downstream raw materials:

deacetylpseudolaric acid A

Refernces

• 1、 Geng, Zhe,Chen, Bin,Chiu, Pauline. "Total synthesis of pseudolaric acid A". . p. 6197 - 6201. Retrieved 2007/10/03.