111060-65-2

Upstream product

• 6216-61-1 (S)-(-)-N-(benzyloxycarbonyl)leucinol 
• 100-39-0 benzyl bromide 
• 61-90-5 L-leucine 
• 7533-40-6 (S)-2-amino-4-methylpentan-1-ol 
• 111060-50-5 (S)-benzyl 2-(dibenzylamino)-4-methylpentanoate 
• 111060-53-8 (S)-2-(N,N-dibenzylamino)-4-methyl-1-pentanol 
• 95084-25-6 (S)-2-dibenzylamino-4-methylpentanoic acid 

Downstream Products

• 111060-90-3 (2S,3S)-3-(dibenzylamino)-5-methylhexan-2-ol 
• 111085-50-8 (2R,3S)-3-(dibenzylamino)-5-methylhexan-2-ol 
• 1529-17-5 phenyltrimethylsilyl ether 
• 127927-67-7 (4S,5R)-4-Dibenzylamino-5-isobutyl-dihydro-furan-2-one 
• 130708-26-8 (R)-4-Dibenzylamino-3-hydroxy-5-phenyl-pentanethioic acid S-(1,1-diethyl-propyl) ester 
• 130953-25-2 (2S,4R)-4-Dibenzylamino-3-hydroxy-2-methyl-5-phenyl-pentanethioic acid S-(1,1-diethyl-propyl) ester 
• 133148-54-6 (5S,1'S)-5-(1'-(dibenzylamino)-3'-methylbutyl)dihydrofuran-2(3H)-one 
• 133148-54-6 (5R,1'S)-5-(1'-(dibenzylamino)-3'-methylbutyl)dihydrofuran-2(3H)-one 
• 133148-61-5 (4R,5S)-5-Dibenzylamino-4-hydroxy-7-methyl-octanoic acid benzylamide 
• 133148-65-9 (4S,5S)-5-Dibenzylamino-4-hydroxy-7-methyl-octanoic acid benzylamide 
• 133148-58-0 (3S,5S)-5-((S)-1-Dibenzylamino-3-methyl-butyl)-3-methyl-dihydro-furan-2-one 
• 133148-58-0 (3S,5R)-5-((S)-1-Dibenzylamino-3-methyl-butyl)-3-methyl-dihydro-furan-2-one 
• 133148-58-0 (3R,5S)-5-((S)-1-Dibenzylamino-3-methyl-butyl)-3-methyl-dihydro-furan-2-one 
• 133148-59-1 (3R,5R)-5-((S)-1-Dibenzylamino-3-methyl-butyl)-3-methyl-dihydro-furan-2-one 

Relevant academic research and scientific papers

Regioselective Fluorination of α-Hydroxy-β-aminophosphonates by Using PyFluor

We report a simple protocol for the synthesis of α-fluoro-β-aminophosphonates by the regioselective fluorination of α-hydroxy-β-aminophosphonates under mild conditions. The fluorination reactions were mediated by the PyFluor reagent and occurred with the retention of configuration. The main products of this reaction were a series of α-fluoro-β-aminophosphonates, which can be used as precursors in the preparation of medicinally important compounds (e.g., dipeptide analogues).

Synthesis of Optically Active α-Trifluoromethylamines by Rearrangement of β-Amino-α-trifluoromethyl Alcohols

The synthesis of various optically active α-trifluoromethylamines has been realized from β-amino-α-trifluoromethyl alcohols via an aziridinium ion intermediate under kinetic conditions.

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

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.

Synthesis and identification of unprecedented selective inhibitors of CK1ε

A small and structure-biased library of enantiopure anti-β-amino alcohols was prepared in a straightforward manner by a simplified version of the Reetz protocol. Antiproliferative activity testing against a panel of five human solid tumor cell lines gave GI50 values in the range 1-20 μM. The reverse screening by computational methods against 58 proteins involved in cancer pointed to kinases as possible therapeutic target candidates. The experimental determination of the interaction with 456 kinases indicated that the compounds behave as selective CK1ε inhibitors. Our results demonstrate that the lead compound represents the first selective CK1ε inhibitor with proven antiproliferative activity in cancer cell lines.

A versatile and efficient approach for the synthesis of chiral 1,3-nitroamines and 1,3-diamines via conjugate addition to new (S,E)-Γ-aminated nitroalkenes derived from L-α-amino acids

New chiral (S,E)-γ-N,N-dibenzylated nitroalkenes 2a-c were synthesized from natural L-(α)-amino acids in five steps with overall yields of 68-88%. The conjugate addition of hydride, methoxide, nitronate and azide nucleophiles to 2a-c led to the corresponding chiral 1,3-nitroamines in 74-90% yield. The conjugate addition of cyanide anion to 2a,b was followed by HNO2 elimination affording chiral aminated acrylonitriles (73-98%). On the other hand, the azide anion reacted with 2a, in acetonitrile, via a [3 + 2]-cycloaddition in which HNO2 was lost, providing the corresponding 1,2,3-triazole derivative. Direct reduction of 1,3- nitroamine derivatives 9a,b produced the corresponding 1,3-diamines in good yields.

DAST mediated preparation of β-fluoro-α-aminophosphonates

Herein, we report a new and convenient method for the synthesis of β-fluoro-α-aminophosphonates starting from naturally occurring l-amino acids. A key step in the synthetic protocol involves nucleophilic fluorination of N,N-dibenzylated-β-amino alcohols with diethylaminosulfur trifluoride (DAST).

Diastereoselective synthesis of N,N-dibenzyl-protected aminoalkyl hydroxyethylamines: Key building blocks for hydroxyethylamine-based BACE1 inhibitor

(Chemical Equation Presented) L-Amino acids were reduced with NaBH 4 followed by reacting with benzyl bromide to give N,N-dibenzyl-protected aminoalkyl ethanol 3, which in turn underwent a Swern oxidation, a Johnson-Corey-Chaykovsky reaction, and a nucleophilic reaction to afford N,N-dibenzyl-protected aminoalkyl hydroxyethylamine 6 with a diastereomer ratio 2.5-2.9:1 of (2R, 3S)-6:(2S, 3S)-6. Copyright Taylor & Francis Group, LLC.

Total synthesis and absolute configuration of (-)-berkeleyamide A

[Chemical equation presented] A chiral-pool approach to (-)-berkeleyamide A 1 based on a diastereoselective nitrile oxide [3 + 2]-cycloaddition completes the first total synthesis establishing the absolute stereochemistry of the natural product.

Chiral ferrocenyl amino alcohols for enantioselective additions of diethylzinc to aldehydes

Optically active ferrocenyl amino alcohols have been prepared from commercially available L-alaninol, L-leucinol and L-valinol. They have been utilized as chiral ligands in the catalytic addition of diethylzinc to aldehydes. The influence of the substitue