153322-12-4

Usage

Uses

Used in Organic Synthesis:
(1S,2R)-N-BENZYL-2-AMINO-1,2-DIPHENYLETHANOL is utilized as a building block in organic synthesis due to its complex and versatile structure, allowing for the creation of a wide range of compounds with potential applications in various industries.
Used in Pharmaceutical Research:
As a chiral molecule, (1S,2R)-N-BENZYL-2-AMINO-1,2-DIPHENYLETHANOL serves as a valuable intermediate in the development of pharmaceuticals. Its unique stereochemistry is crucial for the synthesis of biologically active compounds, making it an essential component in medicinal chemistry.
Used in Drug Development:
The potential pharmacological properties of (1S,2R)-N-BENZYL-2-AMINO-1,2-DIPHENYLETHANOL make it an interesting target for drug development. Researchers explore its capacity to interact with biological targets, which could lead to the discovery of new therapeutic agents.
Used in Medicinal Chemistry Research:
In the field of medicinal chemistry, (1S,2R)-N-BENZYL-2-AMINO-1,2-DIPHENYLETHANOL is employed for studying its interactions with various biological systems. Understanding these interactions can provide insights into the design of more effective drugs and treatments.

InChI:InChI=1/C21H21NO/c23-21(19-14-8-3-9-15-19)20(18-12-6-2-7-13-18)22-16-17-10-4-1-5-11-17/h1-15,20-23H,16H2/t20-,21+/m1/s1

Upstream product

• 162237-42-5 (+/-)-erythro-α'-benzylidenamino-bibenzyl-α-ol; N-benzylidene-dl-diphenylhydroxyethylamine 
• 23364-44-5 (1S,2R)-2-Amino-1,2-diphenylethanol 
• 100-52-7 benzaldehyde 

Downstream Products

• 848572-70-3 Trifluoro-methanesulfinic acid benzyl-((1R,2S)-1,2-diphenyl-2-trimethylsilanyloxy-ethyl)-amide 

Relevant academic research and scientific papers

(β-amino alcohol)(arene)ruthenium(II)-catalyzed asymmetric transfer hydrogenation of functionalized ketones - Scope, isolation of the catalytic intermediates, and deactivation processes

The asymmetric transfer hydrogenation of functionalized ketones with (β-amino alcohol)(arene)RuII catalysts using 2-propanol as the hydrogen source has been studied. The structure of the catalyst has been systematically screened using a wide variety of [(η6-arene)RuCl2]2 complexes and β-amino alcohols R1CH(OH)CHR2NHR3, some of which were specifically designed for optimized performance, e.g. (1S,2R)-N-(4-biphenylmethyl)norephedrine (9ο). The efficiencies of the catalytic combinations have been evaluated in the reduction of β-oxo esters and ketones bearing heteroatoms at the α-position. The catalyst precursor [{η6-p-cymene}{η2-N,O-(9ο)}RuCl] (35), the 16-electron true catalyst [{η6-p-cymene}{η2-N,O-(9ο1-) }Ru] (36), and the hydride [{η6-p-cymene}{η2-N,O-(9ο)}RuH] (37) involved in the reduction process have been isolated, characterized by NMR and ESI-MS, as well as by X-ray crystallography in the case of 35, and their reactivities have been investigated. The results reveal two general trends regarding this catalytic process: (1) the apparent reaction rate and the enantioselectivity are largely controlled by the nature of the amine functionality of the chiral ligand and the arene ring of the RuII precursor; (2) side reactions occur between the ketone substrate and the active catalytic species that affect the concentration of the latter and consequently the apparent rate; the formation of inactive (β-diketonato)RuII complexes is demonstrated in the case of β-oxo esters.

Stereoselective synthesis of δ-lactones from 5-oxoalkanals via one-pot sequential acetalization, tishchenko reaction, and lactonization by cooperative catalysis of samarium ion and mercaptan

By the synergistic catalysis of samarium ion and mercaptan, a series of 5-oxoalkanals was converted to (substituted) δ-lactones in efficient and stereoselective manners. This one-pot procedure comprises a sequence of acetalization, Tishchenko reaction and lactonization. The deliberative use of mercaptan, by comparison with alcohol, is advantageous to facilitate the catalytic cycle. The reaction mechanism and stereochemistry are proposed and supported by some experimental evidence. Such samarium ion/mercaptan cocatalyzed reactions show the feature of remote control, which is applicable to the asymmetric synthesis of optically active δ-lactones. This study also demonstrates the synthesis of two insect pheromones, (2S,5R)-2-methylhexanolide and (R)-hexadecanolide, as examples of a new protocol for asymmetric reduction of long-chain aliphatic ketones.