111138-83-1

Basic information

• Product Name: BENZYL N,N-DIBENZYL-L-PHENYLALANINATE
• Synonyms: BENZYL N,N-DIBENZYL-L-PHENYLALANINATE ;(S)-2-Dibenzylamino-3-phenyl-propionic acid benzyl ester;N,N-Dibenzyl-L-phenylalanine benzyl ester;N,N-Dibenzylphenylalanine benzyl este
• CAS NO: 111138-83-1
• Molecular Formula: C₃₀H₂₉NO₂
• Molecular Weight: 435.55676
• Product Categories: Amino Acids & Derivatives;Aromatics;Chiral Reagents;Intermediates
• Mol File: 111138-83-1.mol
• Article Data: 39

Chemical Properties

• Boiling Point: 566.32oC at 760 mmHg
• Flash Point: 157.565oC
• Appearance: /
• Density: 1.142g/cm3
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.616
• PKA: 5.27±0.50(Predicted)
• CAS DataBase Reference: BENZYL N,N-DIBENZYL-L-PHENYLALANINATE(CAS DataBase Reference)
• NIST Chemistry Reference: BENZYL N,N-DIBENZYL-L-PHENYLALANINATE(111138-83-1)
• EPA Substance Registry System: BENZYL N,N-DIBENZYL-L-PHENYLALANINATE(111138-83-1)

Safety Data

• Hazardous Substances Data: 111138-83-1(Hazardous Substances Data)

Usage

Description

BENZYL N,N-DIBENZYL-L-PHENYLALANINATE, also known as L-N,N-Dibenzylphenylalanine Benzyl Ester (CAS# 111138-83-1), is a chemical compound that is characterized by its light yellow oil appearance. It is primarily used in the field of organic synthesis due to its unique chemical properties.

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 articles and documents

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.

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.

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.