95084-26-7

Upstream product

• 501-53-1 benzyl chloroformate 
• 868-59-7 L-cysteine ethyl ester hydrochloride 
• 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 academic research and scientific papers

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.

Conversion of Thiosulfinate Derivatives of Cystine to Unsymmetrical Cystines and Lanthionines by Reaction with Tris(dialkylamino)phosphines

Synthetic routes to the unsymmetrical lanthionines 2 and 3 have been developed.Reaction of a thiosulfinate, derived by oxidation of the corresponding symmetrical cystine with m-chloroperbenzoic acid, with a protected cysteine in the presence of a tris(dialkylamino)phosphine, hexaethylphosphorus triamide, yielded an unsymmetrical or mixed cystine.Contraction of the disulfide linkage in the appropriate mixed cystine by reaction with hexaethylphosphorus triamide provided the unsymmetrical lanthionines 2 and 3.A second route to unsymmetrical lanthionines was investigated that involved the attempted displacement of sulfonate leaving groups from di- or tripeptides containing a serylvaline residue.The sulfonate ester function was observed to be very unreactive toward displacement by mercaptide anion in these peptides, a fact that may be due to steric or conformational effects originating from the adjacent valine residue.