Tetrangulol methyl ether

Base Information

• Chemical Name: Tetrangulol methyl ether
• CAS No.: 85178-50-3
• Molecular Formula: C₂₀H₁₄O₄
• Molecular Weight: 318.329
• Mol file: 85178-50-3.mol

Synonyms:1-Hydroxy-8-methoxy-3-methylbenz(a)anthracene-7,12-dione;tetrangulol methyl ether;X-14881-E;X-14881;

Chemical Property of Tetrangulol methyl ether

Chemical Property:

• PSA: 63.60000
• LogP: 3.63780

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of Tetrangulol methyl ether

There total 21 articles about Tetrangulol methyl ether 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: 98.0%

(+/-)-rubiginone B2 (56630-78-5,111613-85-5) → 1-Hydroxy-8-methoxy-3-methylbenzanthracene-7,12-dione (85178-50-3)

Guidance literature:

With hydrogenchloride; palladium dichloride; In tert-butyl alcohol; for 0.666667h; Heating;

DOI:10.1016/S0040-4020(00)00869-3

Reference yield: 74.0%

8-O-methyltetrangomycin (131919-12-5,117620-87-8) → 1-Hydroxy-8-methoxy-3-methylbenzanthracene-7,12-dione (85178-50-3)

Guidance literature:

With toluene-4-sulfonic acid; In benzene; for 2h; Reflux;

DOI:10.1002/ejoc.201200049

Reference yield:

3-acetyl-5-methoxy-1,4-naphthoquinone (81418-42-0) → 1-Hydroxy-8-methoxy-3-methylbenzanthracene-7,12-dione (85178-50-3)

Guidance literature:

Multi-step reaction with 5 steps

1.1: NaH; EtOH / 1 h / 0 °C

1.2: 76 percent / K₂CO₃; MeI / acetone / 2.5 h / Heating

2.1: 51 percent / NaOH / ethanol; H₂O / 5.5 h / Heating

3.1: 91 percent / pyridine / CH₂Cl₂ / 0 - 20 °C

4.1: 98 percent / Et₃N; formic acid; Ph₃P / palladium(II) acetate / 3 h / 50 °C

5.1: 98 percent / palldium(II) chloride; conc. HCl / 2-methyl-propan-2-ol / 0.67 h / Heating

With pyridine; hydrogenchloride; sodium hydroxide; formic acid; ethanol; sodium hydride; triethylamine; triphenylphosphine; palladium dichloride; palladium diacetate; In ethanol; dichloromethane; water; tert-butyl alcohol;

DOI:10.1016/S0040-4020(00)00869-3

upstream raw materials:

Tetrangulol

dimethyl sulfate

8-O-methyltetrangomycin

(+/-)-rubiginone B₂

Downstream raw materials:

Tetrangulol

Refernces

• 1、 Ngwira, Kennedy J.,Rousseau, Amanda L.,Johnson, Myron M.,de Koning, Charles B.. "Reactions of [2-(2-Naphthyl)phenyl]acetylenes and 2-(2-Naphthyl)benzaldehyde O-Phenyloximes: Synthesis of the Angucycline Tetrangulol and 1,10,12-Trimethoxy-8-methylbenzo[c]phenanthridine". . p. 1479 - 1488. Retrieved 2017/04/01.
• 2、 Parker, Kathlyn A,Ding, Qing-Jie. "A general approach to angucyclines: Synthesis of hatomarubigin A, rubiginone B2, antibiotic X-1488E, 6-hydroxytetrangulol, and tetrangulol". . p. 10249 - 10254. Retrieved 2007/10/03.