Antibiotic WS 5995B

Base Information

• Chemical Name: Antibiotic WS 5995B
• CAS No.: 76191-52-1
• Molecular Formula: C19H14O6
• Molecular Weight: 338.3109
• Mol file: 76191-52-1.mol

Synonyms:Benzoic acid,2-(1,4-dihydro-5-hydroxy-1,4-dioxo-2-naphthalenyl)-3-methoxy-5-methyl;2-(5-hydroxy-1,4-naphthoquinon-2-yl)-3-methoxy-5-methylbenzoic acid;Antibiotic WS 5995B;WS-5995 B;2-(1,4-Dihydro-5-hydroxy-1,4-dioxo-2-naphthalenyl)-3-methoxy-5-methylbenzoic acid;

Chemical Property of Antibiotic WS 5995B

Chemical Property:

• Vapor Pressure: 1.51E-16mmHg at 25°C
• Boiling Point: 626.2°C at 760 mmHg
• Flash Point: 231.5°C
• PSA: 100.90000
• Density: 1.433g/cm³
• LogP: 2.87000

Purity/Quality:

ANTIBIOTIC WS 5995B 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of Antibiotic WS 5995B

There total 21 articles about Antibiotic WS 5995B 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: 67.0%

gilvocarcin BE-12406X2 → WS-5995 B (76191-52-1)

Guidance literature:

With potassium hydroxide; oxygen; In tetrahydrofuran; at 23 ℃;

DOI:10.1016/S0040-4039(96)02056-4

Reference yield: 53.0%

2-2'-carboxy-6'-methoxy-4'-methylphenyl-5-hydroxy-3-phenylthio-1,4-naphthoquinone (125187-17-9) → WS-5995 B (76191-52-1)

Guidance literature:

With sodium hydroxide; Ra-Ni; for 0.166667h; Heating;

Reference yield:

2,6-Dibromo-4-methylaniline (6968-24-7) → WS-5995 B (76191-52-1)

Guidance literature:

Multi-step reaction with 9 steps

1: 80 percent / cuprous iodide / dimethylformamide / 1 h / 100 °C

2: 95 percent / sulfuric acid / 0.08 h

3: 86 percent / triphenyl phosphine, n-tributyl amine, water / PdCl₂(PPh₃)2 / 18 h / 110 °C / 7600 Torr

4: 95 percent / 10percent NaOH / 1 h / Heating

5: 80 percent / HCl / 4 h

6: 1.) 6N HCl, sodium nitrite / 1.) -10 deg C; 2.) dioxane, water, 80 deg C, 10 min

7: 85 percent / MnO₂ / CH₂Cl₂ / Ambient temperature; 2-3 h

8: 1.) NaBH₄; 2.) MnO₂ / 1.) PdCl₂(PPh)2 / 1.) methanol, 15 min; 2.) DCM, 30 min

With hydrogenchloride; manganese(IV) oxide; sodium hydroxide; sodium tetrahydroborate; copper(l) iodide; tributyl-amine; sulfuric acid; water; triphenylphosphine; sodium nitrite; bis-triphenylphosphine-palladium(II) chloride; PdCl₂(PPh)2; In dichloromethane; N,N-dimethyl-formamide;

DOI:10.1016/S0040-4020(01)86970-2

upstream raw materials:

2-2'-carboxy-6'-methoxy-4'-methylphenyl-5-hydroxy-3-phenylthio-1,4-naphthoquinone

2-(2-methoxycarbonyl-6-methoxy-4-methyl)phenyljuglone

5-Hydroxy-2-<6-methoxy-4-methyl-2-<(diethylamino)carbonyl>phenyl>-1,4-naphthoquinone

2,6-Dibromo-4-methylaniline

Downstream raw materials:

8-hydroxy-1-methoxy-3-methyl-5H-benzonaphtho<2,3-b>pyran-5,7,12-trione

2-(2-methoxycarbonyl-6-methoxy-4-methyl)phenyljuglone

Refernces

• 1、 De Frutos, Oscar,Echavarren, Antonio M.. "Syntheses of fenanthroviridone, gilvocarcin BE-12406X2, and antibiotic WS 599B based on the palladium and copper catalyzed coupling of organostannanes with bromoquinones". . p. 8953 - 8956. Retrieved 2007/10/03.
• 2、 McKenzie, Thomas C.,Choi, Woo-Baeg. "THE TOTAL SYNTHESIS OF THE ANTI-COCCIDIAL AGENTS WS-5995". . p. 1523 - 1532. Retrieved 2007/10/02.