1079950-08-5

Basic information

• Product Name: N-Acetyl-S-(3-aMino-2-hydroxy-3-oxopropyl)-L-cysteine-1,1-diMethylethyl Ester
• Synonyms: N-Acetyl-S-(3-aMino-2-hydroxy-3-oxopropyl)-L-cysteine-1,1-diMethylethyl Ester
• CAS NO: 1079950-08-5
• Molecular Formula: C12H22N2O5S
• Molecular Weight: 306.37848
• Product Categories: Amino Acids & Derivatives;Chiral Reagents
• Mol File: 1079950-08-5.mol
• Article Data: 1

Chemical Properties

• Boiling Point: 569.6±50.0 °C(Predicted)
• Appearance: /
• Density: 1.229±0.06 g/cm3(Predicted)
• Solubility: Dichloromethane
• PKA: 12.54±0.20(Predicted)
• CAS DataBase Reference: N-Acetyl-S-(3-aMino-2-hydroxy-3-oxopropyl)-L-cysteine-1,1-diMethylethyl Ester(CAS DataBase Reference)
• NIST Chemistry Reference: N-Acetyl-S-(3-aMino-2-hydroxy-3-oxopropyl)-L-cysteine-1,1-diMethylethyl Ester(1079950-08-5)
• EPA Substance Registry System: N-Acetyl-S-(3-aMino-2-hydroxy-3-oxopropyl)-L-cysteine-1,1-diMethylethyl Ester(1079950-08-5)

Safety Data

• Hazardous Substances Data: 1079950-08-5(Hazardous Substances Data)

Usage

Chemical Properties

Off-white Solid

Uses

Protected metabolite of Acrylamide.

Upstream product

• 5694-00-8 glycidamide 
• 178432-67-2 t-butyl N-acetyl-(L)-cysteinate 

Relevant articles and documents

Syntheses of D-labelled oxidative metabolites of acrylamide and acrylonitrile for the quantification of their toxicities in humans

Syntheses of the labelled oxidative metabolites of acrylamide and acrylonitrile - reference compounds for the evaluation of human exposure to important toxicants - are reported. For that, L-cystine tert-butyl ester was acetylated and the product reductively cleaved to L-cysteine tert-butyl ester, which reacted with carbamoyl[D3]oxirane (obtained from [D 3]acrylonitrile and 30% aq. H2O2 at pH = 7.0-7.5) and afforded a separable mixture of tert-butyl N-acetyl-S-(2-hydroxy-2- carbamoyl[ D3]ethyl)cysteinate and tert-butyl N-acetyl-S-(1- carbamoyl-2-hydroxy[D3]ethyl)cysteinate (ca. 9:1). Removal of the tert-butyl group in these intermediates with aq. HCl gave the final deuterated internal standards with carbamoyl residues. Protection of the secondary hydroxy group in the major intermediate with tBuMe2SiCl/imidazole in DMF followed by dehydration of the carbamoyl group (trifluoroacetic anhydride/pyridine in CH2Cl2) and stepwise removal of the tert-butyl and tBuMe2Si protecting groups (TFA, Et3SiH, CH2Cl2; aq. HF in MeCN) yielded N-acetyl-S-(2-cyano-2- hydroxy[D3]ethyl)cysteine. Monoprotection of [D4]ethylene glycol with tBuMe2SiCl and NaH in THF, oxidation to tBuMe 2SiOCD2CDO, conversion to tBuMe2SiOCD 2CD(OH)CN and tBuMe2SiOCD2CD(OTs)CN followed by nucleophilic substitution of the tosyloxy group with N-acetyl-L-cysteine (MeOD, Et3N) and deprotection with 4 M HCl in dioxane resulted in N-acetyl-S-(1-cyano-2-hydroxy[D3]ethyl)cysteine. All transformations (except the last but one) gave the respective products in good yields. Wiley-VCH Verlag GmbH & Co. KGaA, 2008.