(+/-)-ergothioneine

Base Information

• Chemical Name: (+/-)-ergothioneine
• CAS No.: 162240-56-4
• Molecular Formula: C₉H₁₅N₃O₂S
• Molecular Weight: 229.303
• Mol file: 162240-56-4.mol

Synonyms:

Chemical Property of (+/-)-ergothioneine

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (+/-)-ergothioneine

There total 5 articles about (+/-)-ergothioneine 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: 92.0%

methyl (S)-3-<1-(ethoxycarbonyl)-2-<(ethoxycarbonyl)thio>-1H-imidazol-4-yl>-2-(trimethylammonio)propionate iodide (162240-57-5) → (+/-)-ergothioneine (162240-56-4)

Guidance literature:

With TEA; In methanol; water; at 60 ℃; for 45h;

DOI:10.1021/jo00125a014

Reference yield:

l-histidine methyl ester dihydrochloride (4467-54-3,5619-10-3,7389-87-9,18684-16-7,22888-60-4,32381-17-2,92742-29-5,100009-20-9) → (+/-)-ergothioneine (162240-56-4)

Guidance literature:

Multi-step reaction with 5 steps

1: H₂ / Pd/C / H₂O / 5 h / 3800 Torr / Ambient temperature

2: 1.) NaHCO₃, ClC(S)OPh, 2.) TEA / 1.) H₂O, THF, room temperature, 5 h, 2.) MeOH, room temperature, 18 h

3: 99 percent / Et₃N / CH₂Cl₂ / 0.5 h / 10 °C

4: 85 percent / tetrahydrofuran / 24 h / Ambient temperature

5: 92 percent / TEA / H₂O; methanol / 45 h / 60 °C

With TEA; hydrogen; sodium hydrogencarbonate; triethylamine; phenylcarbonochloridothioate; palladium on activated charcoal; In tetrahydrofuran; methanol; dichloromethane; water;

DOI:10.1021/jo00125a014

Reference yield:

methyl (S)-3-(2-mercapto-1H-imidazol-4-yl)-2-(dimethylamino)propionate (162138-71-8) → (+/-)-ergothioneine (162240-56-4)

Guidance literature:

Multi-step reaction with 3 steps

1: 99 percent / Et₃N / CH₂Cl₂ / 0.5 h / 10 °C

2: 85 percent / tetrahydrofuran / 24 h / Ambient temperature

3: 92 percent / TEA / H₂O; methanol / 45 h / 60 °C

With TEA; triethylamine; In tetrahydrofuran; methanol; dichloromethane; water;

DOI:10.1021/jo00125a014

upstream raw materials:

methyl (S)-3-<1-(ethoxycarbonyl)-2-<(ethoxycarbonyl)thio>-1H-imidazol-4-yl>-2-(trimethylammonio)propionate iodide

l-histidine methyl ester dihydrochloride

methyl (S)-3-(2-mercapto-1H-imidazol-4-yl)-2-(dimethylamino)propionate

methyl (S)-3-<1-(ethoxycarbonyl)-2-<(ethoxycarbonyl)thio>-1H-imidazol-4-yl>-2-(dimethylamino)propionate