53907-28-1

Basic information

• Product Name: L-Cysteine, N-[(phenylmethoxy)carbonyl]-, methyl ester
• Synonyms: N-[(phenylmethoxy)carbonyl]-L-cysteine methyl ester;Na-(benzyloxycarbonyl)-L-cysteine methyl ester;N-benzyloxycarbonylcysteine methyl ester;N-phenylmethoxycarbonyl-L-cysteine methyl ester;N-Cbz-cysteine methyl ester;Z-Cys-OMe
• CAS NO: 53907-28-1
• Molecular Formula: C12H15NO4S
• Molecular Weight: 269.321
• Mol File: 53907-28-1.mol
• Article Data: 5

Chemical Properties

• Boiling Point: 429.5±45.0 °C(Predicted)
• Density: 1.232±0.06 g/cm3(Predicted)
• CAS DataBase Reference: L-Cysteine, N-[(phenylmethoxy)carbonyl]-, methyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: L-Cysteine, N-[(phenylmethoxy)carbonyl]-, methyl ester(53907-28-1)
• EPA Substance Registry System: L-Cysteine, N-[(phenylmethoxy)carbonyl]-, methyl ester(53907-28-1)

Safety Data

• Hazardous Substances Data: 53907-28-1(Hazardous Substances Data)

Upstream product

• 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 
• 75-09-2 dichloromethane 
• 3693-95-6 N-benzyloxycarbonyl cystine methyl ester 
• 3693-95-6 N,N'-bis[(phenylmethoxy)carbonyl]-L-cystine 1,1'-dimethyl ester 

Downstream Products

• 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 
• 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 
• 21142-83-6 6D-carbobenzyloxyamino-3D-carboxy-2,2-dimethyl-5-oxoperhydro-1,4-thiazepine 
• 77628-08-1 6L-carbobenzoxyamino-3D-carboxy-2,2-dimethyl-5-oxoperhydro-1,4-thiazepine benzhydryl ester 
• 77628-12-7 3D-benzhydryloxycarbonyl-6L-carbobenzoxyamino-2,2-dimethyl-5-oxoperhydro-1,4-thiazepine-1-oxide 
• 28819-05-8 (S)-2-benzyloxycarbonylamino-propionic acid methyl ester 
• 1277170-53-2 S-[[[(1,1-dimethylethyl)dimethylsilyl]oxy]methyl]-N-[(phenylmethoxy)carbonyl]-L-cysteine methyl ester 
• 1227929-17-0 (Z)-methyl 2-(benzyloxycarbonylamino)-3-(2-(2-oxooxazolidin-3-yl)vinylthio)propanoate 
• 1227929-16-9 (E)-methyl 2-(benzyloxycarbonylamino)-3-(2-(2-oxooxazolidin-3-yl)vinylthio)propanoate 
• 1227929-15-8 (Z)-methyl 3-(2-(N-benzylbenzamido)vinylthio)-2-(benzyloxycarbonylamino)propanoate 

Relevant articles and documents

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.

Synthesis and conformations of α-aminoadipyl- and glycyl-α-aminoadipylthiazepine sulfoxides

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