(2E,4E)-2-Methyl-hexa-2,4-dienedioic acid 1-((1S,2S)-2-hydroxy-1,2-diphenyl-ethyl) ester 6-methyl ester

Base Information

• Chemical Name: (2E,4E)-2-Methyl-hexa-2,4-dienedioic acid 1-((1S,2S)-2-hydroxy-1,2-diphenyl-ethyl) ester 6-methyl ester
• CAS No.: 177036-71-4
• Molecular Formula: C₂₂H₂₂O₅
• Molecular Weight: 366.414
• Mol file: 177036-71-4.mol

Synonyms:(2E,4E)-2-Methyl-hexa-2,4-dienedioic acid 1-((1S,2S)-2-hydroxy-1,2-diphenyl-ethyl) ester 6-methyl ester

Chemical Property of (2E,4E)-2-Methyl-hexa-2,4-dienedioic acid 1-((1S,2S)-2-hydroxy-1,2-diphenyl-ethyl) ester 6-methyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2E,4E)-2-Methyl-hexa-2,4-dienedioic acid 1-((1S,2S)-2-hydroxy-1,2-diphenyl-ethyl) ester 6-methyl ester

There total 2 articles about (2E,4E)-2-Methyl-hexa-2,4-dienedioic acid 1-((1S,2S)-2-hydroxy-1,2-diphenyl-ethyl) ester 6-methyl 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:

(2E,4E)-2-Methyl-hexa-2,4-dienedioic acid 6-methyl ester (177036-68-9) → (2E,4E)-2-Methyl-hexa-2,4-dienedioic acid 1-((1S,2S)-2-hydroxy-1,2-diphenyl-ethyl) ester 6-methyl ester (177036-71-4)

Guidance literature:

Multi-step reaction with 2 steps

1: oxalyl chloride / dimethylformamide; CH₂Cl₂ / 1 h / Heating

2: NEt₃ / tetrahydrofuran / Ambient temperature

With oxalyl dichloride; triethylamine; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1021/ja9602509

Reference yield:

(S,S)-hydrobenzoin (2325-10-2) + (2E,4E)-5-Chlorocarbonyl-hexa-2,4-dienoic acid methyl ester → (2E,4E)-2-Methyl-hexa-2,4-dienedioic acid 1-((1S,2S)-2-hydroxy-1,2-diphenyl-ethyl) ester 6-methyl ester (177036-71-4)

Guidance literature:

With triethylamine; In tetrahydrofuran; Yield given; Ambient temperature;

DOI:10.1021/ja9602509

Reference yield:

(2E,4E)-2-Methyl-hexa-2,4-dienedioic acid 1-((1S,2S)-2-hydroxy-1,2-diphenyl-ethyl) ester 6-methyl ester (177036-71-4) → adrenosterone (382-45-6)

Guidance literature:

Multi-step reaction with 8 steps

1: DMAP / tetrahydrofuran / 0 - 20 °C

2: toluene / 18 h / 200 °C

3: K₂CO₃ / 14 h / Ambient temperature

4: 76 percent / Mg, MeOH / 2.5 h / Heating

5: t-BuOK / benzene / 5 h / Heating

6: AcOH, aq. HCl / 1 h / Heating

7: 5percent aq. NaOH / methanol / 1 h / Heating

8: aq. Hg(ClO₄)2 / tetrahydrofuran / 1 h / Ambient temperature

With hydrogenchloride; methanol; dmap; sodium hydroxide; mercury(II) perchlorate; potassium tert-butylate; potassium carbonate; magnesium; acetic acid; In tetrahydrofuran; methanol; toluene; benzene;

DOI:10.1021/ja9602509

upstream raw materials:

(S,S)-hydrobenzoin

(2E,4E)-2-Methyl-hexa-2,4-dienedioic acid 6-methyl ester

Downstream raw materials:

C₄₉H₅₀O₆S₂Si

adrenosterone