85803-44-7

Usage

Chemical Properties

White solid

Upstream product

• 34805-17-9 methyl 2S-amino-3-(4-benzyloxyphenyl)propionate hydrochloride 
• 110-91-8 morpholine 
• 2130-96-3 O-benzyl-N-tert-butoxycarbonyl-L-tyrosine 
• 541-41-3 chloroformic acid ethyl ester 
• 83345-46-4 N-(tert-butyloxycarbonyl)-L-tyrosinol 
• 5034-68-4 4-[(2S)-2-amino-3-hydroxypropyl]phenol 
• 100-39-0 benzyl bromide 
• 127132-32-5 ethyl N-{[(1,1-dimethylethyl)oxy]carbonyl}-O-(phenylmethyl)-L-tyrosinate 
• 72594-77-5 N-(tert-butoxycarbonyl)-L-tyrosine ethyl ester 
• 16652-64-5 O-benzyl-S-tyrosine 
• 60-18-4 L-tyrosine 
• 4326-36-7 (S)-N-(tert-butoxycarbonyl)tyrosine methyl ester 
• 27513-44-6 N-tert-butoxycarbonyl-O-benzyl-(S)-tyrosine methyl ester 
• 1080-06-4 L-Tyr-OMe 

Downstream Products

• 183794-24-3 (S)-1-(4-Benzyloxy-benzyl)-2-[(Z)-4-(tert-butyl-dimethyl-silanyloxy)-but-2-enyloxy]-ethylamine 
• 600738-28-1 N₁,N₃-di{(1S)-1-[4-(benzyloxy)benzyl]-2-hydroxyethyl}-2,2-diethylmanonamide 
• 870450-04-7 6-[(S)-2-(4-Benzyloxy-phenyl)-1-methanesulfonyloxymethyl-ethylcarbamoyl]-nicotinic acid methyl ester 
• 468732-54-9 2,2'-(1-ethylpropylidene)bis[(4S)-4-(4-benzyloxy)benzyl-4,5-dihydro-1,3-oxazole] 
• 600738-30-5 N₁,N₃-di{(1S)-1-[4-(benzyloxy)benzyl]-2-chloroethyl}-2,2-diethylmanonamide 
• 1200694-93-4 (S)-2-(4-(benzyloxy)benzyl)aziridine 
• 109953-93-7 (S)-benzyl 1-(4-(benzyloxy)phenyl)-3-hydroxypropan-2-ylcarbamate 
• 1269269-60-4 (4S)-4-(4'-p-hydroxy)benzyl-4,5-dihydrooxazoline 
• 1394035-45-0 (S)-N₁-((1-(4-benzyloxy)benzyl)-2-hydroxyethyl)-N₂-phenylthiourea 

Relevant academic research and scientific papers

N-[4-phenyl-3-(benzoylamino)-1,1,1-trifluoro-butyl-2-yl]-phenylalaninol derivative as well as preparation method and application thereof

The present invention discloses an N-[4-phenyl-3-(benzoylamino)-1,1,1-trifluoro-butyl-2-yl]-phenylalaninol derivative, which is a compound represented by a general formula I and a pharmaceutically acceptable salt or hydrate thereof, and wherein R1 and R3

Chiral ethylene-bridged flavinium salts: the stereoselectivity of flavin-10a-hydroperoxide formation and the effect of substitution on the photochemical properties

A series of chiral non-racemic N1,N10-ethylene bridged flavinium salts 4 was prepared using enantiomerically pure 2-substituted 2-aminoethanols (R = isopropyl, phenyl, benzyl, 4-methoxybenzyl, 4-benzyloxybenzyl) derived from amino acids as the sole source of chirality. The flavinium salts were shown to form 10a-hydroperoxy- and 10a-methoxy-adducts with moderate to high diastereoselectivity depending on the ethylene bridge substituent originating from the starting amino acid. High diastereoselectivities (dr values from 80:20 to >95:5) were observed for flavinium salts bearing benzyl substituents attached to the ethylene bridge. The benzyl group preferred the face-to-face (syn) orientation relative to the flavinium unit; thereby effectively preventing nucleophilic attack from one side. This conformation was found to be the most stable according to the DFT calculations. Consequently, the presence of benzyl groups causes intermolecular fluorescence quenching resulting in a significant decrease in the fluorescence quantum yield from 11% for 4a bearing an isopropyl substituent to 0.3% for 4c containing a benzyl group and to a value lower than 0.1% for the benzyloxybenzyl derivative 4e.

Soluble polymer supported 2-imidazolidinone chiral auxiliary and method for manufacturing the same

The present invention relates to a chiral auxiliary agent and a manufacturing method thereof and, more specifically, to a 2-imidazolidinone chiral auxiliary agent supported onto a polymer soluble in an organic solvent and a manufacturing method thereof. The chiral auxiliary agent in the present invention shows effects of being easy to separate reaction products and the chiral auxiliary agent after a termination of a reaction while fulfilling an economic efficacy of chiral auxiliary molecules by being supported onto the polymer soluble in the organic solvent.COPYRIGHT KIPO 2015

Rigid spiroethers targeting the decoding center of the bacterial ribosome

Continuing our efforts towards understanding the principles governing ribosomal recognition and function, we have synthesized and evaluated a series of diversely functionalized 5,6-, 6,6- and 7,6-spiroethers. These compounds successfully mimic natural aminoglycosides regarding their binding to the decoding center of the bacterial ribosome. Their potential to inhibit prokaryotic protein production in vitro along with their antibacterial potencies have also been examined.

New practical synthesis of non-cross-linked polystyrene supported 2-phenylimino-2-oxazolidine

A new practical method for the synthesis of a non-cross-linked polystyrene supported 2-phenylimino-2-oxazolidine chiral auxiliary is reported. This method started from the same material as in a previous synthesis, N-Boc-L-tyrosine ethyl ester, but the overall yield was 42.5%, which was higher than the copolymerisation method.

Synthesis of a new chiral auxiliary-Non-cross-linked polystyrene-supported oxazolidine-2-selone

A new chiral auxiliary, non-cross-linked polystyrene-supported oxazolidine-2-selone was synthesized using N-Boc-l-tyrosine ethyl ester as starting material. The structure of the target product was detected by IR, NMR, elemental analysis, and the spectrum

Solid phase asymmetric alkylation reactions using 2-imidazolidinone chiral auxiliary

A novel solid supported 2-imidazolidinone chiral auxiliary was prepared from O-benzyl-l-tyrosine and Wang resin. Asymmetric alkylation reactions in the solid phase proceeded with excellent stereoselectivities, which were even higher than those observed in the conventional solution phase method.

Synthesis of novel N-protected β3-amino nitriles: study of their hydrolysis involving a nitrilase-catalyzed step

Several commercially available nitrilases were investigated with regard to their potential to hydrolyze N-protected β3-amino nitriles into their corresponding N-protected β3-amino acids. The biotransformations were obtained in different proportions depending on the nitrilase involved. The best hydrolysis results were achieved for the N-Cbz-β3-amino nitrile from l-alanine using the NIT-107, in a phosphate buffer at 0.05 M. However, no biotransformation into the corresponding acids was observed for the N-sulfonylamide β3-amino nitriles. Two simple and efficient procedures to prepare the β3-amino nitriles from their analogous α-amino acids are described. Thirty four new substances were synthesized and characterized over the course of this work.

Scope and mechanism of direct indole and pyrrole couplings adjacent to carbonyl compounds: Total synthesis of acremoauxin A and oxazinin 3

Full details are provided for a recently invented method to couple indoles and pyrroles to carbonyl compounds. The reaction is ideally suited for structurally complex substrates and exhibits high levels of chemoselectivity (functional group tolerability), regioselectivity (coupling occurs exclusively at C-3 of indole or C-2 of pyrrole), stereoselectivity (substrate control), and practicality (amenable to scaleup). In addition, quaternary stereocenters are easily and predictably generated. The reaction has been applied to a number of synthetic problems including total syntheses of members of the hapalindole family of natural products, ketorolac, acremoauxin A, and oxazinin 3. Mechanistically, this coupling protocol appears to operate by a single electron-transfer process requiring generation of an electron-deficient radical adjacent to a carbonyl which is then intercepted by an indole or pyrrole anion.

Ligand creation via linking - A rapid and convenient method for construction of novel supported PyOX-ligands

A novel supported amino alcohol linker was synthesized and utilized for attachment of picolinic acid derivatives onto different supports. When the resin bound molecule was further activated, the PyOX-moiety could be constructed reliably in enantiopure form. Furthermore, an efficient Pd-catalyzed modification of a picolinic acid derivative is presented.