Bis-boc-Mitorubrinic acid t-butyl ester

Base Information

• Chemical Name: Bis-boc-Mitorubrinic acid t-butyl ester
• CAS No.: 908291-98-5
• Molecular Formula: C₃₅H₄₀O₁₃
• Molecular Weight: 668.695
• Mol file: 908291-98-5.mol

Synonyms:Bis-boc-Mitorubrinic acid t-butyl ester

Chemical Property of Bis-boc-Mitorubrinic acid t-butyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of Bis-boc-Mitorubrinic acid t-butyl ester

There total 14 articles about Bis-boc-Mitorubrinic acid t-butyl ester 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:

3-(7-hydroxy-7-methyl-6,8-dioxo-7,8-dihydro-6H-isochromen-3-yl)-acrylic acid tert-butyl ester (908291-92-9) + 2,4-bis-tert-butoxycarbonyloxy-6-methyl-benzoic acid (908291-93-0) → Bis-boc-Mitorubrinic acid t-butyl ester (908291-98-5)

Guidance literature:

With dmap; 2,4,6-trichlorobenzoyl chloride; triethylamine; In dichloromethane; toluene; at 40 ℃; for 4h;

DOI:10.1021/ol0610993

Reference yield:

4-O-(t-butoxycarbonyl)-2-hydroxy-3,6-dimethyl methylbenzoate (908292-00-2) → Bis-boc-Mitorubrinic acid t-butyl ester (908291-98-5)

Guidance literature:

Multi-step reaction with 11 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

With 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:

4-O-(t-butoxycarbonyl)-3,6-dimethyl-2-(trimethylsilyl)ethoxy methylbenzoate (908291-86-1) → Bis-boc-Mitorubrinic acid t-butyl ester (908291-98-5)

Guidance literature:

Multi-step reaction with 10 steps

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

1.2: 81 percent / N,N,N',N'-tetramethylethylenediamine / 2 h / -78 °C

2.1: 98 percent / NaH; t-BuOH / tetrahydrofuran; various solvent(s) / -20 - 0 °C

3.1: 73 percent / selenium dioxide / dioxane / 12 h / Heating

4.1: 75 percent / CH₂Cl₂ / 3 h

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

6.1: p-toluenesulfonic acid / 0.08 h

7.1: 86 percent / tetra-n-butylammonium flouride / tetrahydrofuran / 6 h / 20 °C

8.1: 1,2-dichloro-ethane / 0 °C

9.1: 42 mg / o-iodoxybenzoic acid; tetra-n-butylammonium iodide / 1,2-dichloro-ethane / 6 h / 0 °C

10.1: 2,4,6-trichlorobenzoyl chloride; Et₃N; 4-dimethylaminopyridine / CH₂Cl₂; toluene / 4 h / 40 °C

With dmap; n-butyllithium; selenium(IV) oxide; 2,4,6-trichlorobenzoyl chloride; tetrabutyl ammonium fluoride; tetra-(n-butyl)ammonium iodide; sodium hydride; diisobutylaluminium hydride; toluene-4-sulfonic acid; triethylamine; diisopropylamine; 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; 10.1: Yamaguchi reaction;

DOI:10.1021/ol0610993

upstream raw materials:

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

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

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

Downstream raw materials:

mitorubrinic acid

Refernces