N-Desmethyl L-Ergothioneine Methyl Ester

Base Information

• Chemical Name: N-Desmethyl L-Ergothioneine Methyl Ester
• CAS No.: 162138-71-8
• Molecular Formula: C9H15N3O2S
• Molecular Weight: 229.303
• DSSTox Substance ID: DTXSID80433796
• Mol file: 162138-71-8.mol

Synonyms:N-Desmethyl L-Ergothioneine Methyl Ester;162138-71-8;methyl (2S)-2-(dimethylamino)-3-(2-sulfanylidene-1,3-dihydroimidazol-4-yl)propanoate;DTXSID80433796;AKOS030243352;J-009897

Chemical Property of N-Desmethyl L-Ergothioneine Methyl Ester

Chemical Property:

• Boiling Point: 326.7±52.0 °C(Predicted)
• PKA: 11.31±0.70(Predicted)
• PSA: 97.02000
• Density: 1.25±0.1 g/cm3(Predicted)
• LogP: 0.34410
• Storage Temp.: Refrigerator
• Solubility.: Chloroform (Slightly), Methanol (Slightly)
• XLogP3: 0
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 5
• Exact Mass: 229.08849790
• Heavy Atom Count: 15
• Complexity: 302

Purity/Quality:

99% ^*data from raw suppliers

N-DesmethylL-ErgothioneineMethylEster ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CN(C)C(CC1=CNC(=S)N1)C(=O)OC
• Isomeric SMILES: CN(C)[C@@H](CC1=CNC(=S)N1)C(=O)OC
• Uses: Intermediate in the production of L-Ergothioneine

Technology Process of N-Desmethyl L-Ergothioneine Methyl Ester

There total 6 articles about N-Desmethyl L-Ergothioneine 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: 72.0%

N,N-dimethyl histidine methyl ester → methyl (S)-3-(2-mercapto-1H-imidazol-4-yl)-2-(dimethylamino)propionate (162138-71-8)

Guidance literature:

N,N-dimethyl histidine methyl ester; With sodium hydrogencarbonate; phenylcarbonochloridothioate; In diethyl ether; water; at 20 ℃;

With triethylamine; In methanol; at 20 ℃;

DOI:10.1039/c2gc35367a

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) → methyl (S)-3-(2-mercapto-1H-imidazol-4-yl)-2-(dimethylamino)propionate (162138-71-8)

Guidance literature:

Multi-step reaction with 2 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

With TEA; hydrogen; sodium hydrogencarbonate; phenylcarbonochloridothioate; palladium on activated charcoal; In water;

DOI:10.1021/jo00125a014

Reference yield:

Fmoc-L-His(Fmoc)-OH (98929-98-7,200926-18-7) → methyl (S)-3-(2-mercapto-1H-imidazol-4-yl)-2-(dimethylamino)propionate (162138-71-8)

Guidance literature:

Multi-step reaction with 4 steps

1: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; dmap / dichloromethane; methanol / 20 °C

2: trifluoroacetic acid / dichloromethane / 0 °C

3: sodium cyanoborohydride / methanol; water

4: phenylcarbonochloridothioate; sodium hydrogencarbonate / water; diethyl ether

With dmap; sodium cyanoborohydride; sodium hydrogencarbonate; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; trifluoroacetic acid; phenylcarbonochloridothioate; In methanol; diethyl ether; dichloromethane; water;

DOI:10.1002/1873-3468.14303

upstream raw materials:

l-histidine methyl ester dihydrochloride

Fmoc-L-His(Fmoc)-OH

Downstream raw materials:

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

(2S)-3-(2-thioxo-1,3-dihydroimidazol-4-yl)-2-(trimethylammonio) propanoate

(+/-)-ergothioneine

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

Refernces

• 1、 Erdelmeier, Irene,Daunay, Sylvain,Lebel, Remi,Farescour, Laurence,Yadan, Jean-Claude. "Cysteine as a sustainable sulfur reagent for the protecting-group-free synthesis of sulfur-containing amino acids: Biomimetic synthesis of l-ergothioneine in water". supporting information; scheme or table. p. 2256 - 2265. Retrieved 2012/09/08.