400652-45-1

Usage

Uses

Used in Organic Synthesis:
TERT-BUTYL [(1R)-1-CYANO-2-PHENYLETHYL]CARBAMATE is used as a reagent in organic synthesis for its ability to facilitate various chemical reactions, contributing to the formation of complex organic molecules.
Used in Peptide Chemistry:
In peptide chemistry, TERT-BUTYL [(1R)-1-CYANO-2-PHENYLETHYL]CARBAMATE is utilized as a protecting group to shield functional groups from unwanted reactions during the synthesis of peptides, ensuring the desired product is obtained.
Used in Pharmaceutical Research and Development:
TERT-BUTYL [(1R)-1-CYANO-2-PHENYLETHYL]CARBAMATE is used as a potential drug candidate in pharmaceutical research due to its potential biological activity, which is being explored for various therapeutic applications.
Used in Agrochemical Synthesis:
As an important intermediate, TERT-BUTYL [(1R)-1-CYANO-2-PHENYLETHYL]CARBAMATE is used in the synthesis of agrochemicals, playing a crucial role in the development of new pesticides and other agricultural products.
Used in Chemical Research and Development:
TERT-BUTYL [(1R)-1-CYANO-2-PHENYLETHYL]CARBAMATE is employed in the field of chemical research and development for its potential to contribute to the discovery and creation of new chemical entities with practical applications.

Upstream product

• 129095-62-1 (R)-tert-butyl (1-amino-1-oxo-3-phenylpropan-2-yl)carbamate 
• 914955-62-7 [1-(4-methylbenzenesulfonyl)-2-phenylethyl]carbamic acid tert-butyl ester 
• 75-86-5 2-hydroxy-2-methylpropanenitrile 
• 77119-85-8 N-(tert-butoxycarbonyl)-D-phenylalaninal 
• 1033194-57-8 N-Boc D-E/Z-phenylalaninal oxime 
• 19901-50-9 methyl (2R)-2-(t-butoxycarbonylamino)-3-phenylpropionate 
• 13033-84-6 D-phenylalanine methyl ester hydrochloride 

Downstream Products

• 159517-27-8 (R)-2-amino-3-phenylpropanenitrile 

Relevant academic research and scientific papers

Optimization strategy of single-digit nanomolar cross-class inhibitors of mammalian and protozoa cysteine proteases

Cysteine proteases (CPs) are involved in a myriad of actions that include not only protein degradation, but also play an essential biological role in infectious and systemic diseases such as cancer. CPs also act as biomarkers and can be reached by active-

Synthesis and structure-activity relationship of nitrile-based cruzain inhibitors incorporating a trifluoroethylamine-based P2 amide replacement

The structure-activity relationship for nitrile-based cruzain inhibitors incorporating a P2 amide replacement based on trifluoroethylamine was explored by deconstruction of a published series of inhibitors. It was demonstrated that the P3 biphenyl substituent present in the published inhibitor structures could be truncated to phenyl with only a small loss of affinity. The effects of inverting the configuration of the P2 amide replacement and linking a benzyl substituent at P1 were observed to be strongly nonadditive. We show that plotting affinity against molecular size provides a means to visualize both the molecular size efficiency of structural transformations and the nonadditivity in the structure-activity relationship. We also show how the relationship between affinity and lipophilicity, measured by high-performance liquid chromatography with an immobilized artificial membrane stationary phase, may be used to normalize affinity with respect to lipophilicity.

METHOD FOR PRODUCING CHIRAL AMINONITRILES

The invention relates to a method for preparing an N-acyl- or N-sulfonyl-α-aminonitrile, comprising the following steps: a) condensation of an N-acyl- or N-sulfonyl-α-aminoaldehyde with hydroxylamine to give an aldoxime, and b) dehydration of the aldoxime

Synthesis of Enantiomerically Pure N-Acyl Amino Nitriles via Catalytic Dehydration of Oximes and Application in a de Novo Synthesis of Vildagliptin

An alternative route toward enantiomerically highly enriched N-acyl amino nitriles based on the Cu(OAc)2-catalyzed dehydration of aldoximes, which are readily available from N-acyl l- or d-α-amino aldehydes through condensation with hydroxylamine, has been developed. The desired products were obtained with high conversion and in enantiomeric excesses of 97-99% ee. Furthermore, this method has been applied in the synthesis of an N-chloroacetylated 2-cyanopyrrolidine, which represents a building block for the synthesis of Vildagliptin.

One-pot conversion of aldehydes to nitriles mediated by TiCl4

A simple and convenient one-pot synthesis of nitriles from the corresponding aliphatic and aromatic aldehydes has been developed. The titanium tetrachloride assisted reaction was conducted in pyridine under mild conditions using various types of aldehyde precursors and gave the corresponding nitriles in excellent yields. The application of the adopted protocol to isolated aldoxime intermediates provided the corresponding nitriles with yields comparable to those using the one-pot procedure.

The preparation of optically active α-amino 4H-[1,2,4]oxadiazol-5-ones from optically active α-amino acids

Optically active α-amino 4H-[1,2,4]oxadiazol-5-ones (oxadiazolones) were prepared from optically active α-amino acids in five synthetic steps. The oxadiazolone moiety serves as a bioisosteric replacement for the carboxylic acid. Incorporation of an α-amino oxadiazolone into a representative dipeptide mimic is described.

Phase transfer catalyzed enantioselective strecker reactions of α-amido sulfones with cyanohydrins

A study into the use of a chiral phase-transfer catalyst in conjunction with acetone cyanohydrin to effect the enantioselective formation of α-amino nitriles from α-amido sulfones is described. This novel catalytic asymmetric Strecker reaction is analyzed

Design, Synthesis, Molecular Modeling Studies, and Calpain Inhibitory Activity of Novel α-Ketoamides Incorporating Polar Residues at the P 1′-Position

A series of novel α-ketoamides incorporating stereoisomeric residues with different electronic properties at the P1′-position were synthesized to study the electronic requirements for inhibitor binding to the S1′-subsite of calpain I