thielocin A1alpha

Base Information

• Chemical Name: thielocin A1alpha
• CAS No.: 134892-23-2
• Molecular Formula: C₅₄H₆₀O₁₈
• Molecular Weight: 997.06
• Mol file: 134892-23-2.mol

Synonyms:1H-Xanthene-2,7-dicarboxylicacid,4,4a,9,9a-tetrahydro-4,4a-dihydroxy-6-methoxy-3,4,5,8,9a-pentamethyl-1-oxo-,2-[4-[(4-carboxy-3-methoxy-2,5,6-trimethylphenoxy)carbonyl]-3-methoxy-2,5,6-trimethylphenyl]7-(4-carboxy-3-methoxy-2,5,6-trimethylphenyl) ester, (4R,4aR,9aS)-rel- (9CI);1H-Xanthene-2,7-dicarboxylic acid,4,4a,9,9a-tetrahydro-4,4a-dihydroxy-6-methoxy-3,4,5,8,9a-pentamethyl-1-oxo-, 2-[4-[(4-carboxy-3-methoxy-2,5,6-trimethylphenoxy)carbonyl]-3-methoxy-2,5,6-trimethylphenyl]7-(4-carboxy-3-methoxy-2,5,6-trimethylphenyl) ester, (4a,4aa,9ab)-; (?à)-Thieolcin A 1a; Thielocin A 1a

Chemical Property of thielocin A1alpha

Chemical Property:

• Vapor Pressure: 0mmHg at 25°C
• Boiling Point: 1129.8°Cat760mmHg
• Flash Point: 320°C
• PSA: 257.18000
• Density: 1.317g/cm³
• LogP: 7.83380

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of thielocin A1alpha

There total 13 articles about thielocin A1alpha 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: 59.0%

C55H58O19 → thielocin A1β (134892-23-2)

Guidance literature:

With sodium hydroxide; In 1,4-dioxane; at -10 ℃; for 15h;

Reference yield:

ethyl 3-formyl-4,6-dihydroxy-2,5-dimethylbenzoate (148238-89-5) → thielocin A1β (134892-23-2)

Guidance literature:

Multi-step reaction with 8 steps

1: 61 percent / H₂SO₄ / 120 h / 25 °C

2: 90 percent / K₂CO₃ / acetone / 3 h / 50 °C

3: 96 percent / triethylsilane; TFA / 15 h / 25 °C

4: triethylamine / CH₂Cl₂ / 15 h / 25 °C

5: 84 percent / Cd; acetic acid / dimethylformamide / 15 h / 25 °C

6: 83 percent / trifluoroacetic anhydride / benzene / 15 h / 25 °C

7: 80 percent / Cd powder; acetic acid / dimethylformamide / 15 h / 25 °C

8: 59 percent / aq.NaOH / dioxane / 10 h / -10 °C

With triethylsilane; sodium hydroxide; sulfuric acid; potassium carbonate; acetic acid; triethylamine; trifluoroacetic acid; trifluoroacetic anhydride; cadmium; In 1,4-dioxane; dichloromethane; N,N-dimethyl-formamide; acetone; benzene;

DOI:10.1021/ja0112341

Reference yield:

4-Hydroxy-2-methoxy-3,5,6-trimethyl-benzoic acid 2,2,2-trichloro-ethyl ester (153790-86-4) → thielocin A1β (134892-23-2)

Guidance literature:

Multi-step reaction with 5 steps

1: triethylamine / CH₂Cl₂ / 15 h / 25 °C

2: 84 percent / Cd; acetic acid / dimethylformamide / 15 h / 25 °C

3: 83 percent / trifluoroacetic anhydride / benzene / 15 h / 25 °C

4: 80 percent / Cd powder; acetic acid / dimethylformamide / 15 h / 25 °C

5: 59 percent / aq.NaOH / dioxane / 10 h / -10 °C

With sodium hydroxide; acetic acid; triethylamine; trifluoroacetic anhydride; cadmium; In 1,4-dioxane; dichloromethane; N,N-dimethyl-formamide; benzene;

DOI:10.1021/ja0112341

upstream raw materials:

ethyl 3-formyl-4,6-dihydroxy-2,5-dimethylbenzoate

4-Hydroxy-2-methoxy-3,5,6-trimethyl-benzoic acid 2,2,2-trichloro-ethyl ester

3-Formyl-4,6-dihydroxy-2,5-dimethyl-benzoic acid 2,2,2-trichloro-ethyl ester

3-Formyl-4-hydroxy-6-methoxy-2,5-dimethyl-benzoic acid 2,2,2-trichloro-ethyl ester

Refernces

• 1、 Génisson, Yves,Tyler, Peter C.,Young, Robert N.. "Total synthesis of (±)-thielocin A1β: A novel inhibitor of phospholipase A2". . p. 759 - 760. Retrieved 2007/10/02.