211677-21-3

Basic information

• Product Name: ((R)-1-Dimethylcarbamoyl-2-phenyl-ethyl)-carbamic acid tert-butyl ester
• Synonyms: ((R)-1-Dimethylcarbamoyl-2-phenyl-ethyl)-carbamic acid tert-butyl ester
• CAS NO: 211677-21-3
• Molecular Weight: 292.378
• Mol File: 211677-21-3.mol
• Article Data: 5

Chemical Properties

• CAS DataBase Reference: ((R)-1-Dimethylcarbamoyl-2-phenyl-ethyl)-carbamic acid tert-butyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: ((R)-1-Dimethylcarbamoyl-2-phenyl-ethyl)-carbamic acid tert-butyl ester(211677-21-3)
• EPA Substance Registry System: ((R)-1-Dimethylcarbamoyl-2-phenyl-ethyl)-carbamic acid tert-butyl ester(211677-21-3)

Safety Data

• Hazardous Substances Data: 211677-21-3(Hazardous Substances Data)

Upstream product

• 18942-49-9 Boc-D-Phe-OH 
• 124-40-3 dimethyl amine 
• 673-06-3 D-(R)-phenylalanine 
• 24424-99-5 di-tert-butyl dicarbonate 
• 506-59-2 N,N-dimethylammonium chloride 

Downstream Products

• 230643-52-4 D-Phe-NMe₂ 
• 1562416-51-6 C₃₆H₅₀N₆O₆ 
• 1175090-79-5 (R)-2-amino-N,N-dimethyl-3-phenyl-propionamide hydrochloride 

Relevant articles and documents

Structure–Activity Relationship Studies on (R)-PFI-2 Analogues as Inhibitors of Histone Lysine Methyltransferase SETD7

SETD7 is a histone H3K4 lysine methyltransferase involved in human gene regulation. Aberrant expression of SETD7 has been associated with various diseases, including cancer. Therefore, SETD7 is considered a good target for the development of new epigenetic drugs. To date, few selective small-molecule inhibitors have been reported that target SETD7, the most potent being (R)-PFI-2. Herein we report structure–activity relationship studies on (R)-PFI-2 and its analogues. A library of 29 structural analogues of (R)-PFI-2 was synthesized and evaluated for inhibition of recombinantly expressed human SETD7. The key interactions were found to be a salt bridge and a hydrogen bond formed between (R)-PFI-2′s NH2+ group and SETD7′s Asp256 and His252 residue, respectively.

Enantioselective Synthesis of 3-Arylquinazolin-4(3H)-ones via Peptide-Catalyzed Atroposelective Bromination

We report the development of a tertiary amine-containing β-turn peptide that catalyzes the atroposelective bromination of pharmaceutically relevant 3-arylquinazolin-4(3H)-ones (quinazolinones) with high levels of enantioinduction over a broad substrate scope. The structure of the free catalyst and the peptide-substrate complex were explored using X-ray crystallography and 2D-NOESY experiments. Quinazolinone rotational barriers about the chiral anilide axis were also studied using density functional theory calculations and are discussed in light of the high enantioselectivities observed. Mechanistic studies also suggest that the initial bromination event is stereodetermining, and the major monobromide intermediate is an atropisomerically stable, mono-ortho-substituted isomer. The observation of stereoisomerically stable monobromides stimulated the conversion of the tribromide products to other atropisomerically defined products of interest. For example, (1) a dehalogenation Suzuki-Miyaura cross-coupling sequence delivers ortho-arylated derivatives, and (2) a regioselective Buchwald-Hartwig amination procedure installs para-amine functionality. Stereochemical information was retained during these subsequent transformations.

Indole-2-carboxamide inhibitors of human liver glycogen phosphorylase [3]

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