111060-53-8

Basic information

• Product Name: (S)-(+)-2-(N,N-DIBENZYLAMINO)-4-METHYLPENTANOL, 90%
• Synonyms: 1-Pentanol,2-[bis(phenylmethyl)amino]-4-methyl-, (S)-; N,N-Dibenzyl-L-Leucinol
• CAS NO: 111060-53-8
• Molecular Formula: C₂₀H₂₇NO
• Molecular Weight: 297.43
• Mol File: 111060-53-8.mol
• Article Data: 21

Chemical Properties

• Appearance: /
• Refractive Index: n20/D 1.543
• CAS DataBase Reference: (S)-(+)-2-(N,N-DIBENZYLAMINO)-4-METHYLPENTANOL, 90%(CAS DataBase Reference)
• NIST Chemistry Reference: (S)-(+)-2-(N,N-DIBENZYLAMINO)-4-METHYLPENTANOL, 90%(111060-53-8)
• EPA Substance Registry System: (S)-(+)-2-(N,N-DIBENZYLAMINO)-4-METHYLPENTANOL, 90%(111060-53-8)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36
• Hazardous Substances Data: 111060-53-8(Hazardous Substances Data)

Usage

General Description

(S)-(+)-2-(N,N-DIBENZYLAMINO)-4-METHYLPENTANOL, 90% is a chemical compound with a 90% purity level that is commonly used in organic synthesis and pharmaceutical research. It is a chiral amine with a dibenzylamino group and a methylpentanol moiety, making it a versatile building block for the synthesis of various drugs and biologically active compounds. (S)-(+)-2-(N,N-DIBENZYLAMINO)-4-METHYLPENTANOL, 90% is often used as a resolving agent for chiral resolution processes, as well as a catalyst in asymmetric synthesis. Its high purity level makes it suitable for use in sensitive reactions and applications where precise stereochemistry is crucial. Additionally, its unique structure and reactivity make it a valuable tool for the development of new pharmaceuticals and biologically active molecules.

Upstream product

• 691-37-2 4-Methyl-1-pentene 
• 52742-32-2 N,N-dibenzyl-O-benzoylhydroxylamine 
• 7533-40-6 (S)-2-amino-4-methylpentan-1-ol 
• 100-52-7 benzaldehyde 
• 100-39-0 benzyl bromide 
• 61-90-5 L-leucine 
• 111060-50-5 (S)-benzyl 2-(dibenzylamino)-4-methylpentanoate 
• 95084-25-6 (S)-2-dibenzylamino-4-methylpentanoic acid 
• 6216-61-1 (S)-(-)-N-(benzyloxycarbonyl)leucinol 
• 2018-66-8 Z-Leu-OH 

Downstream Products

• 111085-50-8 (2R,3S)-3-(dibenzylamino)-5-methylhexan-2-ol 
• 111060-90-3 (2S,3S)-3-(dibenzylamino)-5-methylhexan-2-ol 
• 697754-01-1 (+)-(2R,3S)-3-(dibenzylamino)-1,1,1-trifluoro-5-methylhexan-2-ol 
• 697753-96-1 (-)-(2S,3S)-3-(dibenzylamino)-1,1,1-trifluoro-5-methylhexan-2-ol 
• 171815-93-3 (2R,1'S)-2-[1-(dibenzylamino)-3-methylbutyl]oxirane 
• 171962-77-9 Dibenzyl-((S)-3-methyl-1-(S)-oxiranyl-butyl)-amine 

Relevant articles and documents

Stereoselective Synthesis of (3R,4S)-Statine Utilising the Iron Acetyl Complex 5-C5H5)Fe(CO)(PPh3)COOMe> as a Chiral Acetate Enolate Equivalent

Diethylaluminium enolates derived from the iron acetyl complex 5-C5H5)Fe(CO)(PPh3)COMe> undergo highly diastereoselective aldol reactions with the homochiral aldehydes: N,N-dibenzyl valinal and N,N-dibenzyl leucinal.The diastereoselectivity is explained in terms of Masamune's model of double asymmetric induction using the concept of matched and mismatched pairs.The matched pair aldol product arising from the reaction with N,N-dibenzyl leucinal is converted into the known γ-amino-β-hydroxy acid, (3R,4S)-statine.

Chiral N-heterocyclic carbene-iridium complexes for asymmetric reduction of prochiral ketimines

Enantioselective reduction of imines to the corresponding chiral secondary amines has been studied using a series of chiral half-sandwich iridium complexes. Chiral N-heterocyclic carbene (NHC) ligands in these complexes were synthesized from readily available, naturally occurring amino acids. Inexpensive phenylsilane was used as a convenient hydrogen donor. Under the optimized conditions, Ir-NHC complexes could reduce ketimines in good yields, albeit with moderate enantiomeric excess (ee). The phenylglycine derived chiral NHC was shown to give the best Ir catalyst and it also gave the maximum ee compared to catalysts prepared from other NHCs in this series. The opposite enantiomer of the reduction product was always obtained while using the Ir complex bearing a valine based NHC. The yields were consistently high with a variety of imine substrates having different steric and electronic demands.

Copper-Catalyzed Regio- and Enantioselective Aminoboration of Unactivated Terminal Alkenes

A CuCl/(R,R)-PTBP-BDPP-catalyzed regioselective and enantioselective aminoboration of simple and unactivated terminal alkenes with bis(pinacolato)diboron (pinB-Bpin) and hydroxylamines has been developed. The amino group and boryl group were incorporated

Discovery of (S)-4-isobutyloxazolidin-2-one as a novel leucyl-tRNA synthetase (LRS)-targeted mTORC1 inhibitor

A series of leucinol analogs were investigated as leucyl-tRNA synthetase-targeted mTORC1 inhibitors. Among them, compound 5, (S)-4-isobutyloxazolidin-2-one, showed the most potent inhibition on the mTORC1 pathway in a concentration-dependent manner. Compound 5 inhibited downstream phosphorylation of mTORC1 by blocking leucine-sensing ability of LRS, without affecting the catalytic activity of LRS. In addition, compound 5 exhibited cytotoxicity against rapamycin-resistant colon cancer cells, suggesting that LRS has the potential to serve as a novel therapeutic target.