23190-16-1

Usage

Uses

Used in Pharmaceutical Industry:
(1R,2S)-2-Amino-1,2-diphenylethanol is used as a chiral auxiliary for Pd(II)-assisted chiral tandem alkylation and carbonylative coupling reactions. Its stereoselective nature makes it a valuable tool in the synthesis of complex organic molecules, particularly in the development of pharmaceutical compounds.
Used in Neuroscience Research:
As a compound with affinity for the NMDA receptor, (1R,2S)-2-Amino-1,2-diphenylethanol is used in neuroscience research to study the function and role of NMDA receptors in the central nervous system. This can lead to a better understanding of neurological disorders and the development of potential therapeutic agents.
Used in Chemical Synthesis:
(1R,2S)-2-Amino-1,2-diphenylethanol is also used as a key intermediate in the synthesis of various organic compounds, particularly those with chiral centers. Its unique structure allows for the creation of novel molecules with potential applications in various industries, including pharmaceuticals, agrochemicals, and materials science.

InChI:InChI=1/C14H15NO/c15-13(11-7-3-1-4-8-11)14(16)12-9-5-2-6-10-12/h1-10,13-14,16H,15H2/t13-,14+/m0/s1

Upstream product

• 530-36-9 threo-1,2-diphenyl-2-aminoethan-1-ol 
• 618-65-5 helicin 
• 441-38-3 benzoin oxime 
• 574-15-2 benzilmonoxime 
• 1689-71-0 2,3-diphenyloxirane 
• 169899-58-5 2-(1-hydroxy-1-phenylmethyl)-4,5-dimethylthiazole 
• 5908-41-8 benzoyltrimethylsilane 
• 588-59-0 stilbene 
• 530-36-9 2-amino-1,2-diphenylethanol 
• 184674-48-4 (+)-(2R,3R)-trans-2,3-diphenylaziridine 
• 131350-15-7 N-[(1R,2S)-2-hydroxy-1,2-diphenylethyl]formamide 
• 77539-19-6 2-benzyloxyimino-1,2-diphenylethane-1-one 
• 412930-21-3 (4R,5R)-2,2-Dimethyl-4,5-diphenyl-oxazolidine 
• 23364-44-5 (1S,2R)-2-Amino-1,2-diphenylethanol 

Downstream Products

• 6275-45-2 dichloro-acetic acid-(α'-hydroxy-bibenzyl-α-ylamide) 
• 530-36-9 (1R,2R)-2-amino-1,2-diphenylethane-1-ol 
• 492-70-6 1,2-diphenyl-1,2-ethanediol 
• 530-36-9 (1S,2S)-2-amino-1,2-diphenylethanol 
• 664371-11-3 α'-salicylidenamino-bibenzyl-α-ol 
• 51675-69-5 2,2,3,3-tetramethyl-7,8-diphenyl-1,4,6-trioxa-9-aza-5λ⁵-phospha-spiro[4.4]nonane 
• 142452-47-9 2,3-Diphenyl-1-oxa-4-aza-spiro[4.5]decane 
• 142452-50-4 2-Benzyl-4,5-diphenyl-oxazolidine 
• 23364-44-5 (1S,2R)-2-Amino-1,2-diphenylethanol 
• 19190-95-5 rel-(4R,5R)-4,5-diphenyloxazolidin-2-one 
• 86286-49-9 cis-4,5-diphenyl-1,3-oxazolidin-2-one 
• 92552-75-5 4,5-diphenyl-2-oxazolidinone 
• 5197-11-5 N-chloroacetyl-2-hydroxy-1,2-diphenylethylamine 
• 1309791-27-2 1,2-diphenyl-2-(trimethylsilyloxy)ethanamine 

Relevant academic research and scientific papers

Double Asymmetric Hydrogenation of α-Iminoketones: Facile Synthesis of Enantiopure Vicinal Amino Alcohols

This study presents an Rh/DuanPhos-catalyzed double asymmetric hydrogenation of α-iminoketones for accessing chiral vicinal amino alcohols, which are privileged motifs in pharmaceuticals, agrochemicals, fine chemicals, chiral auxiliaries, organocatalysts, etc. Compared with existing methods, this methodology has the following advantages, such as one-pot operation, high efficiency, operational simplicity, limited waste, broad reaction scope, and high yields (90 to 96%) and stereoselectivities (up to >99:1 dr; >99.9% ee). In addition, the mechanism of the transformation was revealed to be a stepwise reaction by isolating and analyzing reaction intermediates.

NOVEL METHOD FOR PREPARING (2R)-2-(2-METHOXYPHENYL)-2-(OXANE-4-YLOXY)ETHANE-1-OL COMPOUND, AND INTERMEDIATE USED THEREIN

A novel method for preparing a compound of Chemical Formula 1 is disclosed. The method includes a step of obtaining a compound of Chemical Formula 1 by performing a reduction reaction on a compound of Chemical Formula 2; and an intermediate used therein. According to the preparation method of the present invention, the compound of Chemical Formula 1, which is useful for the production of an acetyl-CoA carboxylase (ACC) inhibitor, can be mass-produced more simply and efficiently than that of a conventional method:

Site-Specific C(sp3)–H Aminations of Imidates and Amidines Enabled by Covalently Tethered Distonic Radical Anions

The utilization of N-centered radicals to synthesize nitrogen-containing compounds has attracted considerable attention recently, due to their powerful reactivities and the concomitant construction of C?N bonds. However, the generation and control of N-centered radicals remain particularly challenging. We report a tethering strategy using SOMO-HOMO-converted distonic radical anions for the site-specific aminations of imidates and amidines with aid of the non-covalent interaction. This reaction features a remarkably broad substrate scope and also enables the late-stage functionalization of bioactive molecules. Furthermore, the reaction mechanism is thoroughly investigated through kinetic studies, Raman spectroscopy, electron paramagnetic resonance spectroscopy, and density functional theory calculations, revealing that the aminations likely involve direct homolytic cleavage of N?H bonds and subsequently controllable 1,5 or 1,6 hydrogen atom transfer.

Stereoinversion of Unactivated Alcohols by Tethered Sulfonamides

The direct, catalytic substitution of unactivated alcohols remains an undeveloped area of organic synthesis. Moreover, catalytic activation of this difficult electrophile with predictable stereo-outcomes presents an even more formidable challenge. Described herein is a simple iron-based catalyst system which provides the mild, direct conversion of secondary and tertiary alcohols to sulfonamides. Starting from enantioenriched alcohols, the intramolecular variant proceeds with stereoinversion to produce enantioenriched 2- and 2,2-subsituted pyrrolidines and indolines, without prior derivatization of the alcohol or solvolytic conditions.

Large-scale preparation of key building blocks for the manufacture of fully synthetic macrolide antibiotics

Key building blocks for the production of fully synthetic macrolides have been scaled-up in first time pilot plant and kilo-lab campaigns. These building blocks have supported the discovery of new macrolide antibiotics as well as ongoing preclinical studies.

Chiral morphine quinoline compound preparation method and chiral amino acid preparation method of compound

The invention provides chiral morpholine compounds. The structural general formula of the chiral morpholine compounds is as shown in the description. The invention further comprises a preparation method of the chiral morpholine compounds. The chiral morpholine compounds are prepared by using benzoin as a starting material, performing reductive amination, and performing chemical resolution on enantiomers and acid-catalyzed ester condensation reaction. The invention further provides amino acid compounds prepared from the chiral morpholine compounds, and a preparation method and application of the amino acid compounds.

Stereoretentive Addition of N-tert-Butylsulfonyl-α-Amido Silanes to Aldehydes, Ketones, α,β-Unsaturated Esters, and Imines

Enantioenriched N-tert-butylsulfonyl-α-amido silanes were successfully reacted with aldehydes, ketones, imines, and α,β-unsaturated esters in the presence of a sub-stoichiometric amount of CsF (0.5 equiv) in 1,2-dimethoxyethane (DME) at -20 °C to afford the corresponding coupling products with up to 89 % enantiospecificity in a retentive manner. Keep your cool! Enantioenriched N-tert-butylsulfonyl-α-amido silanes were successfully reacted with aldehydes, ketones, imines, and α,β-unsaturated esters in the presence of a sub-stoichiometric amount of CsF (0.5 equiv) in 1,2-dimethoxyethane (DME) at -20 °C to afford the corresponding coupling products with up to 89 % enantiospecificity in a retentive manner.

HETEROARYL ACID MORPHOLINONE COMPOUNDS AS MDM2 INHIBITORS FOR THE TREATMENT OF CANCER

The present invention provides MDM2 inhibitor compounds of Formula (I), or the pharmaceutically acceptable salts thereof, wherein the variables are defined above, which compounds are useful as therapeutic agents, particularly for the treatment of cancers. The present invention also relates to pharmaceutical compositions that contain an MDM2 inhibitor of Formula (I).

Solvent-induced reversed stereoselectivity in reciprocal resolutions of mandelic acid and erythro -2-amino-1,2-diphenylethanol

Solvent-induced chirality switching in reciprocal optical resolution between mandelic acid (1) and erythro-2-amino-1,2-diphenylethanol (2) has been demonstrated. The stereochemistry of the deposited salts was controlled by changing the crystallization solvent from 1-PrOH or 1-BuOH to 1,4-dioxane. It was revealed from 1H NMR spectra, thermogravimetric analysis, and X-ray crystallography of the salts that an equimolar amount of the crystallization solvent was incorporated in each diastereomeric salt. On the basis of the crystal structures, it was found that both the hydrogen-bonding ability and the size of the solvent molecule played an important role. Differences in the formed hydrogen-bonding networks (columnar or sheetlike structure) and their packing manner were found to be crucial for the reversed stereoselectivity. Furthermore, pseudopolymorphic salt crystals that incorporated 1,4-dioxane were obtained during the enantioseparation of racemic 2, and their solid-state properties were examined by measurement of their IR spectra. This solvent-induced dual stereocontrol technique was successfully applied to the successive resolution process, eliminating the need to change the resolving agent for access to both enantiomers of 1 and 2.

Pseudoephenamine: A practical chiral auxiliary for asymmetric synthesis

Unrestricted: Pseudoephenamine is introduced as a versatile chiral auxiliary and an alternative to pseudoephedrine in asymmetric synthesis. It is free from regulatory restrictions and leads to remarkable stereocontrol in alkylation reactions, especially in those that form quaternary carbon centers. Amides derived from pseudoephenamine exhibit a high propensity to be crystalline substances, and provide sharp, well-defined signals in NMR spectra. Copyright