3693-95-6

Basic information

• Product Name: Z-CYS-OME
• Synonyms: Z-CYS-OME;N-Benzyloxycarbonyl-L-cystine methyl ester
• CAS NO: 3693-95-6
• Molecular Formula: C₂₄H₂₈N₂O₈S₂
• Molecular Weight: 536.62
• Mol File: 3693-95-6.mol
• Article Data: 12

Chemical Properties

• Boiling Point: 429.5°Cat760mmHg
• Flash Point: 213.5°C
• Appearance: /
• Density: 1.232g/cm³
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.547
• CAS DataBase Reference: Z-CYS-OME(CAS DataBase Reference)
• NIST Chemistry Reference: Z-CYS-OME(3693-95-6)
• EPA Substance Registry System: Z-CYS-OME(3693-95-6)

Safety Data

• Hazardous Substances Data: 3693-95-6(Hazardous Substances Data)

Usage

InChI:InChI=1/C12H15NO4S/c1-16-11(14)10(8-18)13-12(15)17-7-9-5-3-2-4-6-9/h2-6,10,18H,7-8H2,1H3,(H,13,15)

Upstream product

• 186581-53-3 diazomethane 
• 6968-11-2 N,N'-bis(benzyloxycarbonyl)-L-cystine 
• 67-56-1 methanol 
• 32854-09-4 L-cystine dimethyl ester dihydrochloride 
• 501-53-1 benzyl chloroformate 
• 53907-28-1 N-benzyloxycarbonyl-L-cysteine methyl ester 
• 62965-15-5 methyl 2-(R)-(benzyloxycarbonylamino)-3-bromomethylpropionate 
• 7647-01-0 hydrogenchloride 
• 1492-52-0 methyl (S)-2-(benzyloxycarbonlamino)-3-(p-toluenesulfonyl)propionate 
• 1145-80-8 N-(benzyloxycarbonyl)-L-serine 
• 1676-81-9 N-benzyloxycarbonyl-L-serine methyl ester 
• 56-89-3 L-cystine 
• 1277170-53-2 S-[[[(1,1-dimethylethyl)dimethylsilyl]oxy]methyl]-N-[(phenylmethoxy)carbonyl]-L-cysteine methyl ester 
• 1069-29-0 cystine dimethyl ester 

Downstream Products

• 13961-96-1 (Z-Cys-NH₂)2 
• 111961-30-9 N,N'-bis-benzyloxycarbonyl-L-cystine dihydrazide 
• 53907-28-1 N-benzyloxycarbonyl-L-cysteine methyl ester 
• 68836-00-0 N-<(Benzyloxy)carbonyl>-L-cysteine Methyl Ester Sulfinyl Chloride 
• 77826-53-0 N-<(Benzyloxy)carbonyl>-S-oxo-S-(bromomethyl)-L-cysteinol 
• 77826-51-8 N-<(Benzyloxy)carbonyl>-S-oxo-S-methoxy-L-cysteine Methyl Ester 
• 68835-92-7 N-<(Benzyloxy)carbonyl>-S-oxo-S-(chloromethyl)-L-cysteine Methyl Ester 
• 77826-52-9 N-<(Benzyloxy)carbonyl>-S-oxo-S-(bromomethyl)-L-cysteine Methyl Ester 
• 77398-52-8 N-<(Benzyloxy)carbonyl>-S-oxo-S-(chloromethyl)-L-cysteinol 
• 72843-11-9 N-<(Benzyloxy)carbonyl>-S-oxo-S-(chloromethyl)-L-cysteinol 
• 77880-67-2 N-<(Benzyloxy)carbonyl>-S-oxo-S-(chloromethyl)-O-(tetrahydropyranyl)-L-cysteinol 
• 77880-68-3 N-<(Benzyloxy)carbonyl>-S-oxo-S-(chloromethyl)-O-(tetrahydropyranyl)-L-cysteinol 
• 77880-69-4 N-<(Benzyloxy)carbonyl>-S-oxo-S-<(methylthio)methyl>-O-(tetrahydropyranyl)-L-cysteinol 
• 77880-70-7 N-<(Benzyloxy)carbonyl>-S-oxo-S-<(methylthio)methyl>-O-(tetrahydropyranyl)-L-cysteinol 

Relevant articles and documents

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.).

[[(tert-Butyl)dimethylsilyl]oxy]-methylGroup for sulfur protection

Aromatic and aliphatic thiols can be protected by reaction with t-BuMe 2SiOCH2Cl in DMF in the presence of a base (2,6-lutidine or proton sponge); the resulting t-BuMe2SiOCH2SR or t-BuMe2SiOCH2SAr are deprotected by sequential treatment with Bu4NF and I2 to give symmetrical disulfides. Another mode of deprotection involves reaction with a sulfenyl chloride; this process gives an unsymmetrical disulfide and was examined with Me(CH2) 11SCH2OSiMe2Bu-t and three sulfenyl chlorides.

Process for S-Aryl cysteine

The present invention provides methods for preparing S-aryl cysteines in enantiomeric excess of greater than about 96%. Specifically, the present invention provides enantioselective methods for preparing S-aryl cysteines starting from cystine, cysteine or