95364-14-0

Basic information

• Product Name: (S)-2-tert-butoxycarbonylamino-3-phenylthiopropionic acid S-benzyl ester
• Synonyms: (S)-2-tert-butoxycarbonylamino-3-phenylthiopropionic acid S-benzyl ester
• CAS NO: 95364-14-0
• Molecular Weight: 371.5
• Mol File: 95364-14-0.mol
• Article Data: 7

Chemical Properties

• CAS DataBase Reference: (S)-2-tert-butoxycarbonylamino-3-phenylthiopropionic acid S-benzyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: (S)-2-tert-butoxycarbonylamino-3-phenylthiopropionic acid S-benzyl ester(95364-14-0)
• EPA Substance Registry System: (S)-2-tert-butoxycarbonylamino-3-phenylthiopropionic acid S-benzyl ester(95364-14-0)

Safety Data

• Hazardous Substances Data: 95364-14-0(Hazardous Substances Data)

Upstream product

• 13734-34-4 N-tert-butoxycarbonyl-L-phenylalanine 
• 100-53-8 phenylmethanethiol 
• 100-39-0 benzyl bromide 
• 81000-39-7 (S)-2-((tert-butoxycarbonyl)amino)-3-phenylpropanethioic S-acid 
• 1333435-21-4 2-((S)-tert-butoxycarbonylamino)-3-phenylpropionic acid 4-chlorophenyl ester 
• 1274754-60-7 S-(tert-butyl) (2S)-2-[(tert-butoxycarbonyl)amino]-3-phenylpropanethioate 
• 514214-66-5 (S)-tert-butyl (1-(1H-benzo[d][1,2,3]triazol-1-yl)-1-oxo-3-phenylpropan-2-yl)carbamate 

Downstream Products

• 120125-43-1 (S)-tert-butyl (1-oxo-3-phenyl-1-(piperidin-1-yl)propan-2-yl)carbamate 
• 201146-30-7 L-phenylalanine S-benzyl ester 

Relevant articles and documents

Ynamide-Mediated Thioester Synthesis

A novel ynamide-mediated thioester synthesis strategy was developed. Importantly, no detectable racemization was observed for the thioesterifications of carboxylic acids containing an α-chiral center, enabling it to be useful for the synthesis of peptide thioester, which is the key component of native chemical ligation. It is worth mentioning that amino acid side chain functional groups such as -OH and indole -NH are compatible with the reaction conditions, rendering their protection unnecessary. Moreover, this method was also amenable to selenoesters.

Fe-catalyzed thioesterification of carboxylic esters

Second nature: Starting from shelf-stable aryl esters and thiols, a variety of carboxylic acid esters were transformed into the corresponding thioesters with no racemization of labile stereocenters (see scheme). The method was successfully applied in a native chemical-ligation-type peptide formation, which suggests that the thiol may act as a co-catalyst for future 1,2-additions of pronucleophiles to carboxylic esters.

Base catalyzed racemization of amino acid derivatives

Amino acid thioesters used as substrates for a chemo-enzymatic dynamic kinetic resolution (DKR) must be designed with a high enough acidity to be rapidly racemized in the presence of a suitable base. Kinetic data obtained from experimental proton exchange rates are correlated with thermodynamic data for the proton abstraction based on the density functional theory (DFT) calculations. The good correlation obtained allows to evaluate the contribution of different functional groups to the carbon acidity and to define bases able to perform the required racemization.