Etoposide 3',4'-Quinone

Base Information

• Chemical Name: Etoposide 3',4'-Quinone
• CAS No.: 105016-65-7
• Molecular Formula: C₂₈H₂₈O₁₃
• Molecular Weight: 572.523
• Mol file: 105016-65-7.mol

Synonyms:Etoposide 3',4'-Quinone;5-[(5R,5aR,8aR,9S)-9-[(4,6-O-(1R)-Ethylidene-β-D-glucopyranosyl)oxy]-5,5a,6,8,8a,9-hexahydro-6-oxofuro[3',4':6,7]naphtho[2,3-d]-1,3-dioxol-5-yl]-3-Methoxy-3,5-cyclohexadiene-1,2-dione;Etoposide o-Quinone;Etoposide quinone

Chemical Property of Etoposide 3',4'-Quinone

Chemical Property:

• Storage Temp.: Hygroscopic, -20°C Freezer, Under Inert Atmosphere
• Solubility.: Chloroform (Slightly), Methanol (Slightly, Heated, Sonicated)

Purity/Quality:

98.5% ^*data from raw suppliers

Etoposide3'',4''-Quinone ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Uses: Precursor to the semiquinone free radical of Etoposide, believed to inactivate φX174 DNA.

Technology Process of Etoposide 3',4'-Quinone

There total 1 articles about Etoposide 3',4'-Quinone 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: 80.0%

etoposide (33419-42-0) → etoposide ortho-quinone (105016-65-7)

Guidance literature:

With ammonium sulfate; sodium periodate; In 1,4-dioxane;

DOI:10.1021/tx0600595

Reference yield:

etoposide ortho-quinone (105016-65-7) → 3'-desmethoxyetoposide

Guidance literature:

Multi-step reaction with 4 steps

1: pyridine

2: H₂

3: 79 percent / NaNO₂ / acetic acid; tetrahydrofuran

4: 41 percent / NaBH₄ / methanol

With pyridine; sodium tetrahydroborate; hydrogen; sodium nitrite; In tetrahydrofuran; methanol; acetic acid;

DOI:10.1021/jm00127a002

Reference yield:

etoposide ortho-quinone (105016-65-7) → C28H28N2O12

Guidance literature:

Multi-step reaction with 3 steps

1: pyridine

2: H₂

3: 79 percent / NaNO₂ / acetic acid; tetrahydrofuran

With pyridine; hydrogen; sodium nitrite; In tetrahydrofuran; acetic acid;

DOI:10.1021/jm00127a002

upstream raw materials:

etoposide

Downstream raw materials:

(5R,5aR,8aR,9S)-5-(3-Amino-4-hydroxy-5-methoxy-phenyl)-9-((2R,4aR,6R,7R,8R,8aS)-7,8-dihydroxy-2-methyl-hexahydro-pyrano[3,2-d][1,3]dioxin-6-yloxy)-5,8,8a,9-tetrahydro-5aH-furo[3',4':6,7]naphtho[2,3-d][1,3]dioxol-6-one

Refernces

• 1、 Zuman, Peter,Holthuis, Joost J. M.. "Mechanism of electrooxidation of substituted phenols in aqueous solutions: some podophyllotoxin derivates as models". . p. 403 - 406. Retrieved 1988.
• 2、 Gantchev, Tsvetan G.,Hunting, Darel J.. "The ortho-quinone metabolite of the anticancer drug etoposide (VP-16) is a potent inhibitor of the topoisomerase II/DNA cleavable complex". . p. 422 - 428. Retrieved 1998.