95084-26-7

Basic information

• Product Name: N-(benzyloxycarbonyl)-L-cysteine ethyl ester
• Synonyms: N-(benzyloxycarbonyl)-L-cysteine ethyl ester
• CAS NO: 95084-26-7
• Molecular Weight: 283.348
• Mol File: 95084-26-7.mol
• Article Data: 2

Chemical Properties

• CAS DataBase Reference: N-(benzyloxycarbonyl)-L-cysteine ethyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: N-(benzyloxycarbonyl)-L-cysteine ethyl ester(95084-26-7)
• EPA Substance Registry System: N-(benzyloxycarbonyl)-L-cysteine ethyl ester(95084-26-7)

Safety Data

• Hazardous Substances Data: 95084-26-7(Hazardous Substances Data)

Upstream product

• 868-59-7 L-cysteine ethyl ester hydrochloride 
• 501-53-1 benzyl chloroformate 
• 23926-58-1 N,N'-bis(benzyloxycarbonyl)-L-cystine diethyl ester 

Downstream Products

• 1227258-50-5 N-Boc, N-Cbz-L-cysteine disulfide diethyl diester 
• 1227258-52-7 N-CBz,N-Fmoc-L-cysteine disulfide ethyl(N-CBz), methyl(N-Fmoc) diester 
• 1253890-64-0 C₂₇H₃₆N₂O₁₂S₂ 
• 1443746-66-4 (R)-ethyl 2-(((benzyloxy)carbonyl)amino)-3-(((triisopropylsilyl)ethynyl)thio)propanoate 

Relevant articles and documents

One-pot synthesis of unsymmetrical disulfides using 1-chlorobenzotriazole as oxidant: Interception of the sulfenyl chloride intermediate

A high-yielding and low temperature one-pot procedure is described for unsymmetrical disulfide synthesis from two different thiols using 1-chlorobenzotriazole (BtCl) as oxidant. The mechanism of the coupling involves in situ trapping of the sulfenyl chloride intermediate R1SCl by nucleophilic benzotriazole (BtH) to form R1SBt, which protects R1SCl from forming the homodimer R1SSR1. The methodology is applicable to all types of thiol (aliphatic, aromatic, heteroaromatic), with a variation developed for aliphatic-aliphatic couplings. Differentially N-protected cysteines couple to afford the unsymmetrical cystine derivatives in high yield (90%), which serves as a model for the one-pot intermolecular coupling of cysteine-containing peptides to form peptide disulfide heterodimers. Minimal exchange in aromatic-aromatic disulfide synthesis is noted on account of the mild conditions.