111138-83-1

Usage

Uses

Used in Organic Synthesis:
BENZYL N,N-DIBENZYL-L-PHENYLALANINATE is used as a synthetic building block for the creation of various complex organic molecules. Its unique structure allows it to be a valuable component in the synthesis of pharmaceuticals, agrochemicals, and other specialty chemicals.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, BENZYL N,N-DIBENZYL-L-PHENYLALANINATE is used as an intermediate in the development of new drugs. Its specific chemical properties make it a suitable candidate for the synthesis of novel therapeutic agents, potentially leading to the discovery of new treatments for various diseases and conditions.
Used in Agrochemical Industry:
BENZYL N,N-DIBENZYL-L-PHENYLALANINATE is also utilized in the agrochemical industry for the synthesis of new pesticides and other crop protection agents. Its incorporation into these products can contribute to the development of more effective and environmentally friendly solutions for agricultural challenges.
Used in Specialty Chemicals:
In the specialty chemicals sector, BENZYL N,N-DIBENZYL-L-PHENYLALANINATE is employed as a key component in the production of various high-value chemicals. These chemicals can be used in a wide range of applications, from advanced materials to innovative consumer products.

InChI:InChI=1/C30H29NO2/c32-30(33-24-28-19-11-4-12-20-28)29(21-25-13-5-1-6-14-25)31(22-26-15-7-2-8-16-26)23-27-17-9-3-10-18-27/h1-20,29H,21-24H2/t29-/m0/s1

Upstream product

• 63-91-2 L-phenylalanine 
• 100-44-7 benzyl chloride 
• 100-39-0 benzyl bromide 

Downstream Products

• 126773-92-0 (S)-4-Dibenzylamino-3-oxo-5-phenyl-pentanoic acid ethyl ester 
• 156732-12-6 (4S)-4-(N,N-dibenzylamino)-3-oxo-5-phenyl-pentanonitrile 
• 111060-52-7 (S)-2-(dibenzylamino)-3-phenylpropan-1-ol 
• 180193-72-0 ((S)-3-Dibenzylamino-2-oxo-4-phenyl-butyl)-phosphonic acid dimethyl ester 
• 123054-12-6 (2S)-N,N-dibenzylphenylalaninal 
• 220887-32-1 (5S)-2-Amino-5-(N,N-dibenzylamino)-4-oxo-1,6-diphenylhex-2-ene 
• 247575-87-7 2,2,4,4-Tetramethyl-oxazolidine-3-carboxylic acid (1S,3S)-3-dibenzylamino-1-((S)-1-dibenzylamino-2-phenyl-ethyl)-2-oxo-4-phenyl-butyl ester 
• 188774-99-4 tert-butyl 4-(N,N-dibenzylamino)-3-oxo-5-phenylpentanoate 
• 184537-69-7 (3S)-3-(N,N-dibenzyl)amino-1-methylsulfinyl-2-oxo-4-phenylbutane 
• 189562-37-6 (3S)-3-(N,N-dibenzyl)amino-1-hydroxy-1-methylthio-2-oxo-4-phenylbutane 
• 189562-38-7 (3S)-1-acetoxy-3-(N,N-dibenzyl)amino-1-methylthio-2-oxo-4-phenylbutane 
• 109389-10-8 (2R,3S)-3-Amino-4-phenyl-butane-1,2-diol 
• 200616-28-0 Acetic acid (1R,2S)-1-bromomethyl-2-tert-butoxycarbonylamino-3-phenyl-propyl ester 
• 200616-25-7 Acetic acid (1R,2S)-1-bromomethyl-2-dibenzylamino-3-phenyl-propyl ester 

Relevant academic research and scientific papers

An Efficient Stereocontrolled Strategy for the Synthesis of Hydroxyethylene Dipeptide Isosteres

A novel and practical synthesis of hydroxyethylene dipeptide isostere 9 from L-phenylalanine via the formation and stereospecific reduction of an enaminone is described.

Preparation method of ritonavir and lopinavir intermediates

The invention discloses a preparation method of ritonavir and lopinavir intermediates. The method comprises the steps: using L-phenylalanine as a raw material to react with benzyl chloride in potassium carbonate and an alkaline aqueous solution to obtain N, N-dimethylformamide; condensing with acetonitrile under the action of sodium amide; carrying out addition reaction with benzyl magnesium chloride; sequentially reducing enamine and carbonyl by using sodium borohydride/methanesulfonic acid and sodium borohydride/trifluoroacetic acid reagents; obtaining a stereoselective product, namely, dibenzylamino-3-hydroxy-5-amino-1, 2, 4-triazole under the induction effect of a chiral inducer; the stereoselective product reacts with di-tert-butyl methyl dicarbonate in a potassium carbonate/tetrahydrofuran solution, ammonium formate and palladium/carbon are used for reduction debenzylation, and the intermediate BDH is obtained. The preparation method is high in stereoselectivity, the diastereomeric excess (de%) value of the chiral product is high, the reaction steps are short, the product yield is high and generated three wastes are few.

Structural Analysis of Potent Hybrid HIV-1 Protease Inhibitors Containing Bis-tetrahydrofuran in a Pseudosymmetric Dipeptide Isostere

The design, synthesis, and X-ray structural analysis of hybrid HIV-1 protease inhibitors (PIs) containing bis-tetrahydrofuran (bis-THF) in a pseudo-C2-symmetric dipeptide isostere are described. A series of PIs were synthesized by incorporating bis-THF of darunavir on either side of the Phe-Phe isostere of lopinavir in combination with hydrophobic amino acids on the opposite P2/P2′ position. Structure-activity relationship studies indicated that the bis-THF moiety can be attached at either the P2 or P2′ position without significantly affecting potency. However, the group on the opposite P2/P2′ position had a dramatic effect on potency depending on the size and shape of the side chain. Cocrystal structures of inhibitors with wild-type HIV-1 protease revealed that the bis-THF moiety retained similar interactions as observed in the darunavir-protease complex regardless of the position on the Phe-Phe isostere. Analyses of cocrystal structures and molecular dynamics simulations provide insights into optimizing HIV-1 PIs containing bis-THF in non-sulfonamide dipeptide isosteres.

Molecular tools that block maturation of the nuclear lamin A and decelerate cancer cell migration

Lamin A contributes to the structure of nuclei in all mammalian cells and plays an important role in cell division and migration. Mature lamin A is derived from a farnesylated precursor protein, known as prelamin A, which undergoes post-translational cleavage catalyzed by the zinc metalloprotease STE24 (ZPMSTE24). Accumulation of farnesylated prelamin A in the nuclear envelope compromises cell division, impairs mitosis and induces an increased expression of inflammatory gene products. ZMPSTE24 has been proposed as a potential therapeutic target in oncology. A library of peptidomimetic compounds were synthesized and screened for their ability to induce accumulation of prelamin A in cancer cells and block cell migration in pancreatic ductal adenocarcinoma cells. The results of this study suggest that inhibitors of lamin A maturation may interfere with cell migration, the biological process required for cancer metastasis.

A (2 R, 3 S) - 1 - chloro - 3 - tert-butoxy amide - 4 - phenyl - 2 - butanol preparation method

The invention provides a preparation method for (2R,3S)-1-chlorine-3-tert-butoxycarbonylamino-4-phenyl-2-butanol. The preparation method comprises the steps that L-phenylalanine is taken as raw materials, protected by adopting benzyl, esterified and then catalyzed through NMM to generate a mixed anhydride compound, the mixed anhydride compound reacts with diazomethane to generate diazoketone, a reduction reaction and palladium carbon reduction are performed, and finally the intermediate (2R,3S)-1-chlorine-3-tert-butoxycarbonylamino-4-phenyl-2-butanol is obtained. According to the preparation method, the low-cost benzyl is adopted to protect amidogen, the synthetic route is reasonable, the operation technology is simple, safe and high in yield, industrialization can be well achieved, and the production efficiency is improved.

Method for synthesizing ritonavir intermediate

The invention relates to a method for synthesizing a ritonavir intermediate. The intermediate is (S,Z)-5-amino-2-(dibenzylamino)-1,6-diphenylhex-4-en-3-one. The method comprises the following steps: mixing L-phenylalanine, water and sodium hydroxide, adding benzyl chloride, adding heptane, washing the above obtained material with a methanol-water solution, and carrying out reduced pressure evaporation to obtain yellow oil benzyl 2-dibenzylamino-3-phenylpropionate; and dissolving the yellow oil in methyl tert-butyl ether under the protection of nitrogen, reacting the obtained solution with anhydrous acetonitrile, adding sodium hydride, stirring all above materials, slowly dropwise adding a Grignard reagent, cooling, adding anhydrous methanol for hydrolyzing superfluous sodium amide, allowing the obtained solution to stand for layering, extracting the obtained water layer with methyl tert-butyl ether, mixing oil layers, concentrating the obtained oil layer mixture, evaporating the obtained concentrate to obtain oil, adding anhydrous methanol, filtering the oil, and carrying out vacuum drying to obtain white powder which is the ritonavir intermediate (S,Z)-5-amino-2-(dibenzylamino)-1,6-diphenylhex-4-en-3-one. Compared with traditional technologies, the method provided by the invention has the advantages of reaction step simplification, reaction cost reduction, and reduction of use of toxic reagents.

Carbohydrates as efficient catalysts for the hydration of α-amino nitriles

Directed hydration of α-amino nitriles was achieved under mild conditions using simple carbohydrates as catalysts exploiting temporary intramolecularity. A broadly applicable procedure using both formaldehyde and NaOH as catalysts efficiently hydrated a variety of primary and secondary susbtrates, and allowed the hydration of enantiopure substrates to proceed without racemization. This work also provides a rare comparison of the catalytic activity of carbohydrates, and shows that the simple aldehydes at the basis of chemical evolution are efficient organocatalysts mimicking the function of hydratase enzymes. Optimal catalytic efficiency was observed with destabilized aldehydes, and with difficult substrates only simple carbohydrates such as formaldehyde and glycolaldehyde proved reliable.

A - And B -fluorinated aminophosphonates-Synthesis and properties

Interest in synthesis of fluorinated aminophosphonates has grown significantly in recent years due to their promising applications in medicinal and bioorganic chemistry. We report herein efficient and general methods for the synthesis of α- and β-monofluo

An asymmetric pericyclic cascade approach to 3-alkyl-3-aryloxindoles: Generality, applications and mechanistic investigations

The reaction of L-serine derived N-arylnitrones with alkylarylketenes generates asymmetric 3-alkyl-3-aryloxindoles in good to excellent yields (up to 93%) and excellent enantioselectivity (up to 98% ee) via a pericyclic cascade process. The optimization, scope and applications of this transformation are reported, alongside further synthetic and computational investigations. The preparation of the enantiomer of a Roche anti-cancer agent (RO4999200) 1 (96% ee) in three steps demonstrates the potential utility of this methodology.

Synthesis of (S,Z)-5-amino-2-(dibenzylamino)-1,6-diphenylhex-4-en-3-one

L-Phenylalanine taken as a starting material is protected with benzyl chloride and procedure simplified by not charging with ethyl alcohol. Subsequently with the further simplification of skipping the atmospheric distillation of MTBE (methyl tert-butyl ether), (S,Z)-5-amino-2-(dibenzylamino)-1,6-diphenylhex-4-en-3-one, the significant intermediate of Ritonavir and Lopinavir, is obtained from cyanidation, Grignard reaction and reduction.