Albacarcin V

Base Information

• Chemical Name: Albacarcin V
• CAS No.: 82196-88-1
• Molecular Formula: C₂₈H₂₈O₉
• Molecular Weight: 508.525
• NSC Number: 613946,354844
• DSSTox Substance ID: DTXSID20918931
• ChEMBL ID: CHEMBL1728866
• Mol file: 82196-88-1.mol

Synonyms:Albacarcin V;NSC354844;MLS002701849;92841-46-8;8-ethenyl-1-hydroxy-10,12-dimethoxy-4-(3,4,5-trihydroxy-4,6-dimethyloxan-2-yl)naphtho[1,2-c]isochromen-6-one;8-ethenyl-1-hydroxy-10,12-dimethoxy-4-[(2R,3R,4S,5R,6S)-3,4,5-trihydroxy-4,6-dimethyloxan-2-yl]naphtho[1,2-c]isochromen-6-one;NSC 354844;VIRENOMYCIN V;CHEMBL1728866;DTXSID20918931;OMDANBMKOUVKAG-UHFFFAOYSA-N;NSC613946;NSC-354844;NSC-613946;6H-Benzo(d)naphtho(1,2-b)pyran-6-one, 4-(6-deoxy-3-C-methyl-beta-L-gulopyranosyl)-8-ethenyl-1-hydroxy-10,12-dimethoxy-;NCI60_003193;SMR001565441;1,5-Anhydro-6-deoxy-1-(8-ethenyl-1-hydroxy-10,12-dimethoxy-6-oxo-6H-benzo[d]naphtho[1,2-b]pyran-4-yl)-3-C-methylhexitol;4-(6-Deoxy-3-C-methyl-.beta.-gulopyranosyl)-8-vinyl-1-hydroxy-10,12-dimethoxy-6H-benzo[d]naphtho[1,2-b]pyran-6-one (chrysomycin A);6H-Benzo[d]naphtho[1, 4-(6-deoxy-3-C-methyl-.beta.-D-gulopyranosyl)-8-ethenyl-1-hydroxy-10,12-dimethoxy-;6H-Benzo[d]naphtho[1,4-(6-deoxy-3-C-methyl-.beta.-D-gulopyranosyl-8-ethenyl-1-hydroxy-10,12-dimethoxy-

Chemical Property of Albacarcin V

Chemical Property:

• Vapor Pressure: 5.51E-27mmHg at 25°C
• Boiling Point: 799.7°C at 760 mmHg
• Flash Point: 269.6°C
• PSA: 138.82000
• Density: 1.405g/cm³
• LogP: 3.39780
• Storage Temp.: 2-8°C
• Solubility.: DMF: soluble
• XLogP3: 2.9
• Hydrogen Bond Donor Count: 4
• Hydrogen Bond Acceptor Count: 9
• Rotatable Bond Count: 4
• Exact Mass: 508.17333247
• Heavy Atom Count: 37
• Complexity: 867

Purity/Quality:

95-99% ^*data from raw suppliers

ChrysomycinA ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CC1C(C(C(C(O1)C2=C3C(=C(C=C2)O)C(=CC4=C3OC(=O)C5=C4C(=CC(=C5)C=C)OC)OC)O)(C)O)O
• Uses: Chrysomycin A is the major analogue in a complex of C-glycoside antitumour actives isolated from Streptomyces. Chrysomycin A, with a vinyl group in the 8-position, is the most potent analogue of the complex, and is thought to act as an inhibitor of the catalytic activity of human topoisomerase II. Chrysomyin A has a potent antibacterial, antifungal, antiviral and antitumour profile. More recent research on related metabolites, the gilvocarcins, suggests that chrysomycins may act as photoactivated, crosslinkers of DNA to histones. Chrysomycin A is the major analogue in a complex of C-glycoside antitumor actives isolated from Streptomyces. Chrysomycin A, with a vinyl group in the 8-position, is the most potent analogue of the complex, and is thought to act as an inhibitor of the catalytic activity of human topoisomerase II. Chrysomycin A has a potent antibacterial, antifungal, antiviral and antitumor profile. More recent research on related metabolites, the gilvocarcins, suggests that chrysomycins may act as photoactivated cross-linkers of DNA to histones. Chrysomycin A is a potent antibacterial, antifungal and antiviral compound.

Technology Process of Albacarcin V

There total 9 articles about Albacarcin V 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: 78.0%

C34H34O12 → chrysomycin A (82196-88-1)

Guidance literature:

With sulfuric acid; In methanol; at 70 ℃; for 7h;

Reference yield:

C20H27BO4 → chrysomycin A (82196-88-1)

Guidance literature:

Multi-step reaction with 6 steps

1.1: dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂; potassium hydroxide / tert-butyl methyl ether; water / 23 h / 80 °C / Inert atmosphere

1.2: 20 h / 80 °C / Inert atmosphere

2.1: dipotassium peroxodisulfate; silver nitrate / acetonitrile; water / 17 h / 50 °C

3.1: 5%-palladium/activated carbon; hydrogen / methanol / 13 h / -78 - 20 °C

3.2: 1 h / -78 °C

4.1: dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂; triethylamine / propan-1-ol / 4 h / 100 °C / Inert atmosphere

5.1: dichloromethane / 2 h / 20 °C / Inert atmosphere; Molecular sieve

5.2: 38.5 h / 0 - 20 °C / Inert atmosphere; Molecular sieve

6.1: sulfuric acid / methanol / 7 h / 70 °C

With dipotassium peroxodisulfate; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂; sulfuric acid; 5%-palladium/activated carbon; hydrogen; silver nitrate; triethylamine; potassium hydroxide; In methanol; propan-1-ol; dichloromethane; tert-butyl methyl ether; water; acetonitrile;

Reference yield:

C29H28O6 → chrysomycin A (82196-88-1)

Guidance literature:

Multi-step reaction with 5 steps

1.1: dipotassium peroxodisulfate; silver nitrate / acetonitrile; water / 17 h / 50 °C

2.1: 5%-palladium/activated carbon; hydrogen / methanol / 13 h / -78 - 20 °C

2.2: 1 h / -78 °C

3.1: dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂; triethylamine / propan-1-ol / 4 h / 100 °C / Inert atmosphere

4.1: dichloromethane / 2 h / 20 °C / Inert atmosphere; Molecular sieve

4.2: 38.5 h / 0 - 20 °C / Inert atmosphere; Molecular sieve

5.1: sulfuric acid / methanol / 7 h / 70 °C

With dipotassium peroxodisulfate; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂; sulfuric acid; 5%-palladium/activated carbon; hydrogen; silver nitrate; triethylamine; In methanol; propan-1-ol; dichloromethane; water; acetonitrile;

upstream raw materials:

1-isopropoxy-10,12-dimethoxy-8-vinyl-6H-naphtho[1,2-b]benzo[d]pyran-6-one

1-isopropoxy-10,12-dimethoxy-8-trifluoromethanesulfonyl-6H-naphtho[1,2-b]benzo[d]pyran-6-one

4-bromo-8-methoxynaphthalen-1-ol

1-bromo-4-isopropoxy-5-methoxynaphthalene

Refernces