Tetracenomycin A2

Base Information

• Chemical Name: Tetracenomycin A2
• CAS No.: 82277-62-1
• Molecular Formula: C23H18O8
• Molecular Weight: 422.3842
• DSSTox Substance ID: DTXSID80231658
• Nikkaji Number: J248.138C
• Wikidata: Q27114812
• Metabolomics Workbench ID: 54503
• Mol file: 82277-62-1.mol

Synonyms:Tcm A2;tetracenomycin A2

Chemical Property of Tetracenomycin A2

Chemical Property:

• Vapor Pressure: 3.19E-19mmHg at 25°C
• Boiling Point: 681.9°Cat760mmHg
• Flash Point: 240.8°C
• PSA: 119.36000
• Density: 1.445g/cm³
• LogP: 3.13860
• XLogP3: 4.1
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 8
• Rotatable Bond Count: 4
• Exact Mass: 422.10016753
• Heavy Atom Count: 31
• Complexity: 737

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1=C(C(=CC2=CC3=C(C(=C12)O)C(=O)C4=C(C3=O)C=C(C=C4O)OC)OC)C(=O)OC

Technology Process of Tetracenomycin A2

There total 4 articles about Tetracenomycin A2 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:

5,8-Dihydroxy-3-methoxy-1-methyl-9,10-dioxo-9,10-dihydro-anthracene-2-carboxylic acid methyl ester (144686-02-2) → tetracenomycin A2 (82277-62-1)

Guidance literature:

Multi-step reaction with 2 steps

1: NaBH₄ / 0 °C

2: 2) HCl, air / 2) MeOH

With hydrogenchloride; sodium tetrahydroborate; air;

DOI:10.1016/S0040-4039(00)61155-3

Reference yield:

methyl 6-deoxykermesate (141111-38-8) → tetracenomycin A2 (82277-62-1)

Guidance literature:

Multi-step reaction with 3 steps

1: Ag₂O

2: NaBH₄ / 0 °C

3: 2) HCl, air / 2) MeOH

With hydrogenchloride; sodium tetrahydroborate; air; silver(l) oxide;

DOI:10.1016/S0040-4039(00)61155-3

Reference yield:

(Z)-(1,3-dimethoxybuta-1,3-dienyloxy)trimethylsilane (106875-55-2) + 9-hydroxy-3-methoxy-1-methyl-5,8-dioxo-5,8-dihydroanthracene-2-carboxylic acid methyl ester (144686-06-6) → tetracenomycin A2 (82277-62-1)

Guidance literature:

With hydrogenchloride; air; Yield given. Multistep reaction; 2) MeOH;

DOI:10.1016/S0040-4039(00)61155-3

upstream raw materials:

diazomethane

(Z)-(1,3-dimethoxybuta-1,3-dienyloxy)trimethylsilane

9-hydroxy-3-methoxy-1-methyl-5,8-dioxo-5,8-dihydroanthracene-2-carboxylic acid methyl ester

5,8-Dihydroxy-3-methoxy-1-methyl-9,10-dioxo-9,10-dihydro-anthracene-2-carboxylic acid methyl ester

Downstream raw materials:

Tetracenomycinon C

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