162240-57-5

Basic information

• Product Name: N(Im)-Ethoxycarbonyl-S-ethoxycarbonyl L-Ergothioneine Methyl Ester Iodide
• Synonyms: N(Im)-Ethoxycarbonyl-S-ethoxycarbonyl L-Ergothioneine Methyl Ester Iodide;(S)-1-(Ethoxycarbonyl)-2-[(ethoxycarbonyl)thio]-α-(Methoxycarbonyl)-N,N,N-triMethyl-1H-iMidazole-4-ethanaMiniuM Iodide
• CAS NO: 162240-57-5
• Molecular Formula: C16H26IN3O6S
• Molecular Weight: 515.36361
• Product Categories: Amino Acids & Derivatives;Heterocycles;Intermediates & Fine Chemicals;Pharmaceuticals;Amino Acids & Derivatives, Heterocycles, Pharmaceuticals, Intermediates & Fine Chemicals
• Mol File: 162240-57-5.mol
• Article Data: 2

Chemical Properties

• Appearance: /
• CAS DataBase Reference: N(Im)-Ethoxycarbonyl-S-ethoxycarbonyl L-Ergothioneine Methyl Ester Iodide(CAS DataBase Reference)
• NIST Chemistry Reference: N(Im)-Ethoxycarbonyl-S-ethoxycarbonyl L-Ergothioneine Methyl Ester Iodide(162240-57-5)
• EPA Substance Registry System: N(Im)-Ethoxycarbonyl-S-ethoxycarbonyl L-Ergothioneine Methyl Ester Iodide(162240-57-5)

Safety Data

• Hazardous Substances Data: 162240-57-5(Hazardous Substances Data)

Usage

InChI:InChI=1/C16H26N3O6S.HI/c1-7-24-15(21)18-10-11(17-14(18)26-16(22)25-8-2)9-12(13(20)23-6)19(3,4)5;/h10,12H,7-9H2,1-6H3;1H/q+1;/p-1/t12-;/m0./s1

Upstream product

• 162138-72-9 methyl (S)-3-<1-(ethoxycarbonyl)-2-<(ethoxycarbonyl)thio>-1H-imidazol-4-yl>-2-(dimethylamino)propionate 
• 74-88-4 methyl iodide 
• 162138-71-8 methyl (S)-3-(2-mercapto-1H-imidazol-4-yl)-2-(dimethylamino)propionate 
• 4467-54-3 l-histidine methyl ester dihydrochloride 

Relevant articles and documents

Cysteine as a sustainable sulfur reagent for the protecting-group-free synthesis of sulfur-containing amino acids: Biomimetic synthesis of l-ergothioneine in water

Biomass-derived cysteine was used as a sustainable sulfur source for the synthesis of rare sulfur-containing amino acids, such as l-ergothioneine (4), which might be a new vitamin, and various l- or d-2-thiohistidine compounds. Key in this simple, one-pot two-step procedure in water is a bromine-induced regioselective introduction of cysteine followed by a novel thermal cleavage reaction in the presence of thiols, a safer alternative to hazardous red phosphorus. Besides avoiding hazardous sulfur reagents, the new protecting-group-free approach reduces drastically the total number of steps, compared to described procedures. The main drawback, i.e. handling of liquid bromine as an activating and oxidizing reagent in water, was addressed by evaluating four alternative methods using in situ generation of bromine or HOBr, and first encouraging results are described.