9-(4,5-Dihydroxy-6-methyloxan-2-yl)-3,4a,8,12b-tetrahydroxy-3-methyl-2,4-dihydrobenzo[a]anthracene-1,7,12-trione

Base Information

• Chemical Name: 9-(4,5-Dihydroxy-6-methyloxan-2-yl)-3,4a,8,12b-tetrahydroxy-3-methyl-2,4-dihydrobenzo[a]anthracene-1,7,12-trione
• CAS No.: 26055-63-0
• Molecular Formula: C₂₅H₂₆O₁₀
• Molecular Weight: 486.475
• NSC Number: 184398
• Wikipedia: Aquayamycin
• ChEMBL ID: CHEMBL1996599
• Mol file: 26055-63-0.mol

Synonyms:aquayamycin

Chemical Property of 9-(4,5-Dihydroxy-6-methyloxan-2-yl)-3,4a,8,12b-tetrahydroxy-3-methyl-2,4-dihydrobenzo[a]anthracene-1,7,12-trione

Chemical Property:

• Vapor Pressure: 9.09E-26mmHg at 25°C
• Boiling Point: 782.2°Cat760mmHg
• PKA: 6.03±0.70(Predicted)
• Flash Point: 268.9°C
• PSA: 181.82000
• Density: 1.65g/cm³
• LogP: -0.21460
• XLogP3: -1.2
• Hydrogen Bond Donor Count: 6
• Hydrogen Bond Acceptor Count: 10
• Rotatable Bond Count: 1
• Exact Mass: 486.15259702
• Heavy Atom Count: 35
• Complexity: 1050

Purity/Quality:

99% ^*data from raw suppliers

AQUAYAMYCIN 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1C(C(CC(O1)C2=C(C3=C(C=C2)C(=O)C4=C(C3=O)C=CC5(C4(C(=O)CC(C5)(C)O)O)O)O)O)O

Technology Process of 9-(4,5-Dihydroxy-6-methyloxan-2-yl)-3,4a,8,12b-tetrahydroxy-3-methyl-2,4-dihydrobenzo[a]anthracene-1,7,12-trione

There total 24 articles about 9-(4,5-Dihydroxy-6-methyloxan-2-yl)-3,4a,8,12b-tetrahydroxy-3-methyl-2,4-dihydrobenzo[a]anthracene-1,7,12-trione 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: 68.0%

Methanesulfonic acid (3R,4aR,5R,12bS)-9-((2R,4R,5S,6R)-4,5-dihydroxy-6-methyl-tetrahydro-pyran-2-yl)-3,4a,8,12b-tetrahydroxy-3-methyl-1,7,12-trioxo-1,2,3,4,4a,5,6,7,12,12b-decahydro-benzo[a]anthracen-5-yl ester (314270-81-0) → aquayayamycin (26055-63-0)

Guidance literature:

With N-ethyl-N,N-diisopropylamine; In 1,4-dioxane; at 40 ℃; for 1h; Inert atmosphere;

DOI:10.1039/C9OB00121B

Reference yield:

Methanesulfonic acid (3R,4aR,5R,12bS)-9-((2R,4R,5S,6R)-4,5-dihydroxy-6-methyl-tetrahydro-pyran-2-yl)-3,4a,8,12b-tetrahydroxy-7,12-dimethoxy-3-methyl-1-oxo-1,2,3,4,4a,5,6,12b-octahydro-benzo[a]anthracen-5-yl ester (314270-78-5) → aquayayamycin (26055-63-0)

Guidance literature:

Multi-step reaction with 4 steps

1: caesium carbonate / N,N-dimethyl-formamide / 2 h / 0 - 20 °C / Inert atmosphere

2: diammonium cerium(IV) nitrate / water; acetonitrile / 0.17 h / 0 °C / Inert atmosphere

3: hydrogen; 5%-palladium/activated carbon / ethyl acetate; methanol / 0.5 h / 20 °C

4: N-ethyl-N,N-diisopropylamine / 1,4-dioxane / 3 h / 20 °C

With diammonium cerium(IV) nitrate; 5%-palladium/activated carbon; hydrogen; caesium carbonate; N-ethyl-N,N-diisopropylamine; In 1,4-dioxane; methanol; water; ethyl acetate; N,N-dimethyl-formamide; acetonitrile;

DOI:10.1002/chem.201604697

Reference yield:

Methanesulfonic acid (3R,4aR,5R,12bS)-8-benzyloxy-9-((2R,4R,5S,6R)-4,5-dihydroxy-6-methyl-tetrahydro-pyran-2-yl)-3,4a,12b-trihydroxy-7,12-dimethoxy-3-methyl-1-oxo-1,2,3,4,4a,5,6,12b-octahydro-benzo[a]anthracen-5-yl ester (314270-79-6) → aquayayamycin (26055-63-0)

Guidance literature:

Multi-step reaction with 3 steps

1: diammonium cerium(IV) nitrate / water; acetonitrile / 0.17 h / 0 °C / Inert atmosphere

2: hydrogen; 5%-palladium/activated carbon / ethyl acetate; methanol / 0.5 h / 20 °C

3: N-ethyl-N,N-diisopropylamine / 1,4-dioxane / 3 h / 20 °C

With diammonium cerium(IV) nitrate; 5%-palladium/activated carbon; hydrogen; N-ethyl-N,N-diisopropylamine; In 1,4-dioxane; methanol; water; ethyl acetate; acetonitrile;

DOI:10.1002/chem.201604697

upstream raw materials:

methanol

vineomycin A₁

kerriamycin B

kerryamycin C