(-)-Mitorubrinic acid

Base Information

• Chemical Name: (-)-Mitorubrinic acid
• CAS No.: 908291-85-0
• Molecular Formula: C₂₁H₁₆O₉
• Molecular Weight: 412.353
• UNII: RG5P6FYE53
• ChEMBL ID: CHEMBL1485208
• Mol file: 908291-85-0.mol

Synonyms:mitorubrinic acid

Chemical Property of (-)-Mitorubrinic acid

Chemical Property:

• XLogP3: 2.2
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 9
• Rotatable Bond Count: 5
• Exact Mass: 412.07943208
• Heavy Atom Count: 30
• Complexity: 923

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: CC1=CC(=CC(=C1C(=O)OC2(C(=O)C=C3C=C(OC=C3C2=O)C=CC(=O)O)C)O)O
• Isomeric SMILES: CC1=CC(=CC(=C1C(=O)OC2(C(=O)C=C3C=C(OC=C3C2=O)/C=C/C(=O)O)C)O)O

Technology Process of (-)-Mitorubrinic acid

There total 15 articles about (-)-Mitorubrinic acid 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: 31.0%

Bis-boc-Mitorubrinic acid t-butyl ester (908291-98-5) → mitorubrinic acid (908291-85-0)

Guidance literature:

With hydrogenchloride; In 1,4-dioxane; for 4h; Heating;

DOI:10.1021/ol0610993

Reference yield:

4-O-(t-butoxycarbonyl)-2-hydroxy-3,6-dimethyl methylbenzoate (908292-00-2) → mitorubrinic acid (908291-85-0)

Guidance literature:

Multi-step reaction with 12 steps

1.1: 99 percent / triphenylphosphine; diisopropyl diazodicarboxylate / tetrahydrofuran / 1 h

2.1: diisopropylamine; nBuLi / tetrahydrofuran; various solvent(s) / -78 - 0 °C

2.2: 81 percent / N,N,N',N'-tetramethylethylenediamine / 2 h / -78 °C

3.1: 98 percent / NaH; t-BuOH / tetrahydrofuran; various solvent(s) / -20 - 0 °C

4.1: 73 percent / selenium dioxide / dioxane / 12 h / Heating

5.1: 75 percent / CH₂Cl₂ / 3 h

6.1: diisobutylaluminum hydride / tetrahydrofuran; various solvent(s) / -78 - 20 °C

7.1: p-toluenesulfonic acid / 0.08 h

8.1: 86 percent / tetra-n-butylammonium flouride / tetrahydrofuran / 6 h / 20 °C

9.1: 1,2-dichloro-ethane / 0 °C

10.1: 42 mg / o-iodoxybenzoic acid; tetra-n-butylammonium iodide / 1,2-dichloro-ethane / 6 h / 0 °C

11.1: 2,4,6-trichlorobenzoyl chloride; Et₃N; 4-dimethylaminopyridine / CH₂Cl₂; toluene / 4 h / 40 °C

12.1: 31 percent / HCl / dioxane / 4 h / Heating

With hydrogenchloride; dmap; n-butyllithium; selenium(IV) oxide; di-isopropyl azodicarboxylate; 2,4,6-trichlorobenzoyl chloride; tetrabutyl ammonium fluoride; tetra-(n-butyl)ammonium iodide; sodium hydride; diisobutylaluminium hydride; toluene-4-sulfonic acid; triethylamine; diisopropylamine; triphenylphosphine; tert-butyl alcohol; 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione; In tetrahydrofuran; 1,4-dioxane; dichloromethane; 1,2-dichloro-ethane; toluene; 1.1: Mitsunobu reaction / 11.1: Yamaguchi reaction;

DOI:10.1021/ol0610993

Reference yield:

3-(7-hydroxy-7-methyl-6,8-dioxo-7,8-dihydro-6H-isochromen-3-yl)-acrylic acid tert-butyl ester (908291-92-9) → mitorubrinic acid (908291-85-0)

Guidance literature:

Multi-step reaction with 2 steps

1: 2,4,6-trichlorobenzoyl chloride; Et₃N; 4-dimethylaminopyridine / CH₂Cl₂; toluene / 4 h / 40 °C

2: 31 percent / HCl / dioxane / 4 h / Heating

With hydrogenchloride; dmap; 2,4,6-trichlorobenzoyl chloride; triethylamine; In 1,4-dioxane; dichloromethane; toluene; 1: Yamaguchi reaction;

DOI:10.1021/ol0610993

upstream raw materials:

Bis-boc-Mitorubrinic acid t-butyl ester

4-O-(t-butoxycarbonyl)-2-hydroxy-3,6-dimethyl methylbenzoate

3-(7-hydroxy-7-methyl-6,8-dioxo-7,8-dihydro-6H-isochromen-3-yl)-acrylic acid tert-butyl ester

2,4-bis-tert-butoxycarbonyloxy-6-methyl-benzoic acid

Refernces