(+)-1,3,8,11-Tetrahydroxy-10-(4-hydroxy-2-oxopentyl)-2-methyl-5,12-naphthacenedione

Base Information

• Chemical Name: (+)-1,3,8,11-Tetrahydroxy-10-(4-hydroxy-2-oxopentyl)-2-methyl-5,12-naphthacenedione
• CAS No.: 150829-94-0
• Molecular Formula: C₂₄H₂₀O₈
• Molecular Weight: 436.418
• DSSTox Substance ID: DTXSID50934068
• Nikkaji Number: J557.382C
• Wikidata: Q82909909
• Metabolomics Workbench ID: 101221
• Mol file: 150829-94-0.mol

Synonyms:UCE6

Chemical Property of (+)-1,3,8,11-Tetrahydroxy-10-(4-hydroxy-2-oxopentyl)-2-methyl-5,12-naphthacenedione

Chemical Property:

• Vapor Pressure: 4.78E-27mmHg at 25°C
• Boiling Point: 800.6°Cat760mmHg
• Flash Point: 451.9°C
• PSA: 152.36000
• Density: 1.555g/cm³
• LogP: 2.62850
• XLogP3: 2.9
• Hydrogen Bond Donor Count: 5
• Hydrogen Bond Acceptor Count: 8
• Rotatable Bond Count: 4
• Exact Mass: 436.11581759
• Heavy Atom Count: 32
• Complexity: 767

Purity/Quality:

99% ^*data from raw suppliers

UCE6 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1=C(C=C2C(=C1O)C(=O)C3=C(C4=C(C=C(C=C4C=C3C2=O)O)CC(=O)CC(C)O)O)O

Technology Process of (+)-1,3,8,11-Tetrahydroxy-10-(4-hydroxy-2-oxopentyl)-2-methyl-5,12-naphthacenedione

There total 19 articles about (+)-1,3,8,11-Tetrahydroxy-10-(4-hydroxy-2-oxopentyl)-2-methyl-5,12-naphthacenedione 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: 76.0%

1,8,11-trihydroxy-10-[2-(2-hydroxy-propyl)-[1,3]dioxolan-2-ylmethyl]-3-methoxymethoxy-2-methyl-naphthacene-5,12-dione (500770-34-3) → (+/-)-UCE6 (150829-94-0)

Guidance literature:

With lithium tetrafluoroborate; In tetrahydrofuran; water; acetonitrile; at 70 ℃; for 72h;

DOI:10.7164/antibiotics.55.1076

Reference yield:

2-methylbenzene-1,3-diol (608-25-3) → (+/-)-UCE6 (150829-94-0)

Guidance literature:

Multi-step reaction with 8 steps

1.1: 87 percent / NaH / dimethylformamide / 0.5 h / 0 - 20 °C

2.1: 78 percent / s-BuLi / tetrahydrofuran / 0.5 h / -78 - 20 °C

3.1: 82 percent / s-BuLi; TMEDA / tetrahydrofuran / 0.5 h / -78 - 20 °C

4.1: AcOH / 16 h / 80 °C

4.2: i-Pr₂NEt / dimethylformamide / 0.5 h / -40 - 20 °C

5.1: LiN(TMS)2 / tetrahydrofuran / 2 h / -78 - 60 °C

5.2: 64 percent / BnOMe / Pd-C / toluene / 15 h / 110 °C

6.1: 85 percent / t-BuOK / H₂O; 2-methyl-propan-2-ol / 0.25 h / 60 °C

7.1: 90 percent / H₂ / Pd(OH)2-C / dioxane / 2 h / 20 °C

8.1: 76 percent / LiBF₄ / tetrahydrofuran; acetonitrile; H₂O / 72 h / 70 °C

With lithium tetrafluoroborate; N,N,N,N,-tetramethylethylenediamine; potassium tert-butylate; hydrogen; sec.-butyllithium; sodium hydride; acetic acid; lithium hexamethyldisilazane; palladium hydroxide - carbon; In tetrahydrofuran; 1,4-dioxane; water; N,N-dimethyl-formamide; acetonitrile; tert-butyl alcohol;

DOI:10.7164/antibiotics.55.1076

Reference yield:

1,3-bis(methoxymethoxy)-2-methylbenzene (221449-83-8) → (+/-)-UCE6 (150829-94-0)

Guidance literature:

Multi-step reaction with 7 steps

1.1: 78 percent / s-BuLi / tetrahydrofuran / 0.5 h / -78 - 20 °C

2.1: 82 percent / s-BuLi; TMEDA / tetrahydrofuran / 0.5 h / -78 - 20 °C

3.1: AcOH / 16 h / 80 °C

3.2: i-Pr₂NEt / dimethylformamide / 0.5 h / -40 - 20 °C

4.1: LiN(TMS)2 / tetrahydrofuran / 2 h / -78 - 60 °C

4.2: 64 percent / BnOMe / Pd-C / toluene / 15 h / 110 °C

5.1: 85 percent / t-BuOK / H₂O; 2-methyl-propan-2-ol / 0.25 h / 60 °C

6.1: 90 percent / H₂ / Pd(OH)2-C / dioxane / 2 h / 20 °C

7.1: 76 percent / LiBF₄ / tetrahydrofuran; acetonitrile; H₂O / 72 h / 70 °C

With lithium tetrafluoroborate; N,N,N,N,-tetramethylethylenediamine; potassium tert-butylate; hydrogen; sec.-butyllithium; acetic acid; lithium hexamethyldisilazane; palladium hydroxide - carbon; In tetrahydrofuran; 1,4-dioxane; water; acetonitrile; tert-butyl alcohol;

DOI:10.7164/antibiotics.55.1076

upstream raw materials:

1,8,11-trihydroxy-10-[2-(2-hydroxy-propyl)-[1,3]dioxolan-2-ylmethyl]-3-methoxymethoxy-2-methyl-naphthacene-5,12-dione

2-methylbenzene-1,3-diol

1,3-bis(methoxymethoxy)-2-methylbenzene

Benzoic acid (E)-5-hydroxy-hexa-3,5-dienyl ester

Refernces