Chaparrin

Base Information

• Chemical Name: Chaparrin
• CAS No.: 4616-50-6
• Molecular Formula: C20H28O7
• Molecular Weight: 380.44
• UNII: YX31WC5SRV
• Nikkaji Number: J34.213K
• Wikidata: Q27106140
• NCI Thesaurus Code: C1767
• Metabolomics Workbench ID: 137404
• ChEMBL ID: CHEMBL470984
• Mol file: 4616-50-6.mol

Synonyms:chaparrin

Chemical Property of Chaparrin

Chemical Property:

• Vapor Pressure: 8.87E-17mmHg at 25°C
• Boiling Point: 597.7°C at 760 mmHg
• Flash Point: 212.9°C
• PSA: 116.45000
• Density: 1.45g/cm³
• LogP: -0.04200
• XLogP3: -0.7
• Hydrogen Bond Donor Count: 4
• Hydrogen Bond Acceptor Count: 7
• Rotatable Bond Count: 0
• Exact Mass: 380.18350323
• Heavy Atom Count: 27
• Complexity: 736

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1C2CC(=O)OC3C24COC(C1O)(C4C5(C(C3)C(=CC(C5O)O)C)C)O
• Isomeric SMILES: C[C@@H]1[C@@H]2CC(=O)O[C@H]3[C@@]24CO[C@@]([C@@H]1O)([C@@H]4[C@@]5([C@@H](C3)C(=C[C@@H]([C@H]5O)O)C)C)O

Technology Process of Chaparrin

There total 1 articles about Chaparrin 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:

shinjuglycoside A → (-)-chaparrinone (4616-50-6)

Guidance literature:

With β-glucosidase; In water; at 37 ℃; for 336h; pH 5.0;

DOI:10.1246/bcsj.57.2496

Reference yield:

chaparrin (4616-50-6) → castelanone (70424-54-3)

Guidance literature:

Multi-step reaction with 7 steps

1: 88 percent / imidazole / dimethylformamide / 48 h / Ambient temperature

2: pyridine / CHCl₃ / 2 h / Ambient temperature

3: 1.) lithium diisopropylamide; 2.) MoO₅, pyridine, HMPA / 1.) THF, -78 deg C, 2 h; 2.) THF, -44 deg C, 4 h

4: pyridine; CH₂Cl₂ / 5 h / Ambient temperature

5: 1N HCl / methanol / 0.25 h / Ambient temperature

6: H₂CrO₄ / acetone / 0.05 h / Ambient temperature

7: tetrabutylammonium fluoride / tetrahydrofuran / 0.5 h / Ambient temperature

With pyridine; 1H-imidazole; hydrogenchloride; N,N,N,N,N,N-hexamethylphosphoric triamide; tetrabutyl ammonium fluoride; chromic acid; {MoO(O₂)2}; lithium diisopropyl amide; In tetrahydrofuran; pyridine; methanol; dichloromethane; chloroform; N,N-dimethyl-formamide; acetone;

DOI:10.1016/S0040-4039(00)87397-9

Reference yield:

(-)-chaparrinone (4616-50-6) → C27H40O7 (83117-10-6)

Guidance literature:

Multi-step reaction with 6 steps

1: 51 percent / p-toluenesulfonic acid / dimethylformamide / 84 h / 40 °C

2: 99 percent / pyridine / CHCl₃ / 1.75 h

3: 1.) LDA, 2.) hexamethylphosphoric triamide / 1.) THF, -78 degC, 2 h. 2.) -20 degC to 0 degC

4: 99 percent / HCl / methanol / 0.25 h / Ambient temperature

5: Jones reagent / acetone / 0.05 h / Ambient temperature

6: aqueous HF / acetonitrile / 6 h / Ambient temperature

With pyridine; hydrogenchloride; N,N,N,N,N,N-hexamethylphosphoric triamide; jones reagent; hydrogen fluoride; toluene-4-sulfonic acid; lithium diisopropyl amide; In methanol; chloroform; N,N-dimethyl-formamide; acetone; acetonitrile;

DOI:10.1016/S0040-4020(01)81638-0

Downstream raw materials:

C₂₇H₄₀O₇

15-heptyl chaparrinones

castelanone

Refernces