53907-28-1

Upstream product

• 3693-95-6 N,N'-bis[(phenylmethoxy)carbonyl]-L-cystine 1,1'-dimethyl ester 
• 3693-95-6 N-benzyloxycarbonyl cystine methyl ester 
• 75-09-2 dichloromethane 
• 501-53-1 benzyl chloroformate 
• 67-56-1 methanol 
• 96289-13-3 N-benzyloxycarbonyl-L-cysteine 
• 6968-11-2 N,N'-bis(benzyloxycarbonyl)-L-cystine 

Downstream Products

• 23435-52-1 (S)-2-[(R)-2-Benzyloxycarbonylamino-3-((R)-2-benzyloxycarbonylamino-2-methoxycarbonyl-ethyldisulfanyl)-propionylamino]-3-hydroxy-propionic acid methyl ester 
• 95018-02-3 methyl N^a-(benzyloxycarbonyl)<thio>-L-cysteinate 
• 95018-03-4 (R)-2-Benzyloxycarbonylamino-3-{4-[(1-biphenyl-4-yl-1-methyl-ethoxycarbonyl)-methyl-amino]-butyrylsulfanyl}-propionic acid methyl ester 
• 21149-17-7 methyl 2-(benzyloxycarbonylamino)acrylate 
• 137196-99-7 (R)-2-Benzyloxycarbonylamino-3-(2-cyano-ethylsulfanyl)-propionic acid methyl ester 
• 191721-67-2 (R)-2-Benzyloxycarbonylamino-3-(1,2-diacetoxy-ethylsulfanyl)-propionic acid methyl ester 
• 226899-29-2 (R)-2-Benzyloxycarbonylamino-3-((R)-2-benzyloxycarbonylamino-2-methoxycarbonyl-ethylsulfanylmethylsulfanyl)-propionic acid methyl ester 
• 297730-82-6 N-phenylmethoxycarbonyl-S-(2,3,4-tri-O-acetyl-6-O,N-carbonylidene-5-deoxy-1,5-imino-β-D-glucopyranosyl)-L-cysteine methyl ester 
• 426213-69-6 (R)-2-Benzyloxycarbonylamino-3-[(1R,2R)-2-tert-butoxycarbonylamino-3-hydroxy-1-(6-methoxy-benzo[1,3]dioxol-5-yl)-propylsulfanyl]-propionic acid methyl ester 
• 755005-24-4 (R)-2-Benzyloxycarbonylamino-3-((1R,2S,5R)-2-isopropyl-5-methyl-cyclohexyloxymethylsulfanyl)-propionic acid methyl ester 
• 77628-09-2 6L-carbobenzoxyamino-3D-carboxy-2,2-dimethyl-5-oxoperhydro-1,4-thiazepine p-nitrobenzyl ester 
• 77628-07-0 3D-carboxy-6L-carbobenzoxyamino-2,2-dimethyl-5-oxoperhydro-1,4-thiazepine methyl ester 
• 77647-80-4 3D-carboxy-6D-carbobenzoxyamino-2,2-dimethyl-5-oxoperhydro-1,4-thiazepine methyl ester 
• 21142-82-5 6L-carbobenzyloxyamino-3D-carboxy-2,2-dimethyl-5-oxoperhydro-1,4-thiazepine 

Relevant academic research and scientific papers

Pd/BIPHEPHOS is an Efficient Catalyst for the Pd-Catalyzed S-Allylation of Thiols with High n-Selectivity

The Pd-catalyzed S-allylation of thiols with stable allylcarbonate and allylacetate reagents offers several advantages over established reactions for the formation of thioethers. We could demonstrate that Pd/BIPHEPHOS is a catalyst system which allows the transition metal-catalyzed S-allylation of thiols with excellent n-regioselectivity. Mechanistic studies showed that this reaction is reversible under the applied reaction conditions. The excellent functional group tolerance of this transformation was demonstrated with a broad variety of thiol nucleophiles (18 examples) and allyl substrates (9 examples), and could even be applied for the late-stage diversification of cephalosporins, which might find application in the synthesis of new antibiotics. (Figure presented.).

Visible-Light-Mediated S?H Bond Insertion Reactions of Diazoalkanes with Cysteine Residues in Batch and Flow

We describe the application of S?H bond insertion reactions of aryl diazoacetates with cysteine residues that enabled metal-free, S?H functionalization under visible-light conditions. Moreover, this process could be intensified by a continuous-flow photomicroreactor on the acceleration of the reaction (6.5 min residence time). The batch and flow protocols described were applied to obtain a wide range of functionalized cysteine derivatives and cysteine-containing dipeptides, thus providing a straightforward and general platform for their functionalizations in mild conditions. (Figure presented.).

A new efficient method for S-CH2-S bond formation and its application to a djenkolic acid-containing cyclic enkephalin analog

An efficient methylene insertion reaction to construct an S-CH2-S bridge between two cysteine residues occurred when the thiol-protecting dimethylphosphinothioyl (Mpt) group of Z-Cys(Mpt)-OMe was removed with tetrabutylammonium fluoride hydrate in CH2Cl2. The thiol-free form gave similar results, albeit the yields were somewhat lower. In both cases, the best yields were obtained using 2 molar amounts of the reagent. Higher amounts of the reagent reduced the yield because of dehydroalanine formation. In the case of penicillamine, the thiol-free form was better in reactivity than the S-Mpt form, which required double the amount of the reagent to give the same yield. The reaction was successfully used in a synthesis of a cyclic enkephalin analog with the S-CH2-S bridge.

Highly Efficient Propane-1,3-dithiol Mediated Thiol-disulphide Interchange: a Facile and Clean Methodology for S-S Reduction in Peptides

Propane-1,3-dithiol, at room temperature and in the absence of any promoter, neatly brings about the S-S -> 2SH change, and the latter can be isolated as acrylonitrile adducts; the methodology has been tested with several substrates including c-lysozyme, insulin and oxytocin, and spontaneous imidazole promoted S-deprotection was observed in the case of Z-Cys(S-CH2CH2CN)His-OMe.