82659-84-5

Usage

InChI:InChI=1/C12H13NO3/c1-8-10(12(14)15-2)13-11(16-8)9-6-4-3-5-7-9/h3-8,10H,1-2H3/t8-,10-/m0/s1

Upstream product

• 79893-89-3 N-benzoyl-L-threonine methyl ester 
• 27696-01-1 (2S,3R)-threo-N-benzoyl-threonine 
• 99843-24-0 (4S)-5t-methyl-2-phenyl-4,5-dihydro-oxazole-4r-carboxylic acid 
• 99843-24-0 (+/-)-5t-methyl-2-phenyl-4,5-dihydro-oxazole-4r-carboxylic acid 
• 98-88-4 benzoyl chloride 
• 3373-59-9 (2S,3S)-methyl 2-amino-3-hydroxybutanoate 
• 75-07-0 acetaldehyde 
• 3373-59-9 L-threonine methyl ester 
• 5333-86-8 ethyl benzimidate hydrochloride 
• 60143-52-4 L-threonine methyl ester hydrochloride 
• 65-85-0 benzoic acid 
• 267653-05-4 N-benzoyl-(2S,3S)-threonine methyl ester 
• 39994-75-7 L-threonine methyl ester hydrochloride 
• 7471-86-5 methyl benzimidate 

Downstream Products

• 114041-55-3 (4R/S,5S)-(4-2H)-4,5-Dihydro-5-methyl-2-phenyloxazol-4-carbonsaeure-methylester 
• 88318-71-2 (4S,5S)-4-Ethyl-4,5-dihydro-5-methyl-2-phenyloxazol-4-carbonsaeure-methylester 
• 88318-69-8 (4S,5S)-4,5-Dihydro-4,5-dimethyl-2-phenyloxazol-4-carbonsaeure-methylester 
• 88318-67-6 Lithium; methoxy-[(S)-5-methyl-2-phenyl-oxazol-(4E)-ylidene]-methanolate 
• 223505-36-0 (4S,5S)-4-[(S)-3-(1,3-Dioxo-1,3-dihydro-isoindol-2-yl)-1-methoxycarbonylmethyl-propyl]-5-methyl-2-phenyl-4,5-dihydro-oxazole-4-carboxylic acid methyl ester 
• 28954-12-3 (2S,3S)-2-amino-3-hydroxybutanoic acid 
• 129783-77-3 (4R,5S)-2-phenyl-4-(hydroxymethyl)-5-methyl-4,5-dihydrooxazole 
• 100063-41-0 methyl 5-methyl-2-phenyloxazole-4-carboxylate 

Relevant academic research and scientific papers

Phosphorus-Based Organocatalysis for the Dehydrative Cyclization of N-(2-Hydroxyethyl)amides into 2-Oxazolines

A metal-free, biomimetic catalytic protocol for the cyclization of N-(2-hydroxyethyl)amides to the corresponding 2-oxazolines (4,5-dihydrooxazoles), promoted by the 1,3,5,2,4,6-triazatriphosphorine (TAP)-derived organocatalyst tris(o-phenylenedioxy)cyclotriphosphazene (TAP-1) has been developed. This approach requires less precatalyst compared to the reported relevant systems, with respect to the phosphorus atom (the maximum turnover number (TON) ～30), and exhibits a broader substrate scope and higher functional-group tolerance, providing the functionalized 2-oxazolines with retention of the configuration at the C(4) stereogenic center of the 2-oxazolines. Widely accessible β-amino alcohols can be used in this approach, and the cyclization of N-(2-hydroxyethyl)amides provides the desired 2-oxazolines in up to 99% yield. The mechanism of the reaction was studied by monitoring the reaction using spectral and analytical methods, whereby an 18O-labeling experiment furnished valuable insights. The initial step involves a stoichiometric reaction between the substrate and TAP-1, which leads to the in situ generation of the catalyst, a catechol cyclic phosphate, as well as to a pyrocatechol phosphate and two possible active intermediates. The dehydrative cyclization was also successfully conducted on the gram scale.

The rapid synthesis of oxazolines and their heterogeneous oxidation to oxazoles under flow conditions

A rapid flow synthesis of oxazolines and their oxidation to the corresponding oxazoles is reported. The oxazolines are prepared at room temperature in a stereospecific manner, with inversion of stereochemistry, from β-hydroxy amides using Deoxo-Fluor. The

Synthesis of 2-oxazolines by in situ desilylation and cyclodehydration of β-hydroxyamides

A powerful method for the synthesis of 2-oxazolines from silyl-protected β-hydroxyamides is reported. Using diethylaminosulfur trifluoride (DAST) or its tetrafluoroborate salt (XtalFluor-E), silyl-protected β-amidoalcohols can be in situ deprotected and d

Synthesis of 2-oxazolines and related N-containing heterocycles using [Et2NSF2]BF4 as a cyclodehydration agent

The preparation of 2-oxazolines and related N-containing heterocycles from the corresponding hydroxyamides using XtalFluor-E ([Et2NSF 2s]BF4) as a cyclodehydration agent is described. A wide range of heterocycles are obtai

ETHYNYLBENZENE DERIVATIVES

Disclosed are compounds of formulae (I), (II), and (II)I: and pharmaceutically acceptable salts thereof, wherein the variables, R, R1, R2, R3, R101, L, D, Q, Y, X, and Z are defined herein. These compounds are useful for treating Gram-negative bacteria infections.

Syntheses, structures and antibiotic activities of LpxC inhibitors based on the diacetylene scaffold

Compounds inhibiting LpxC in the lipid A biosynthetic pathway are promising leads for novel antibiotics against multidrug-resistant Gram-negative pathogens. We report the syntheses and structural and biochemical characterizations of LpxC inhibitors based on a diphenyl-diacetylene (1,4-diphenyl-1,3-butadiyne) threonyl-hydroxamate scaffold. These studies provide a molecular interpretation for the differential antibiotic activities of compounds with a substituted distal phenyl ring as well as the absolute stereochemical requirement at the C2, but not C3, position of the threonyl group.

Structure-activity relationship of new anti-tuberculosis agents derived from oxazoline and oxazole benzyl esters

During the syntheses and studies of natural iron chelators (mycobactins), we serendipitously discovered that a simple, small molecule, oxazoline-containing intermediate 3 displayed surprising anti-tuberculosis activity (MIC of 7.7?μM, average). Herein we

Modular phosphite-oxazoline/oxazine ligand library for asymmetrie Pd-catalyzed allylic substitution reactions: scope and limitations - origin of enantioselectivity

A library of phosphite-oxazoline/oxazine ligands L1-L15a-h has been synthesized and screened in the Pd-catalyzed allylic substitution reactions of several substrate types. These series of ligands can be prepared efficiently from easily accessible hydroxyl amino acid derivatives. Their modular nature enables the substituents/configurations in the oxazoline/oxazine moiety, alkyl backbone chain and in the biaryl phosphite moiety to be easily and systematically varied. By carefully selecting the ligand components, therefore, high regio- and enantioselectivities (ee values up to 99%) and good activities have been achieved in a broad range of mono- and disubstituted linear hindered and unhindered liner and cyclic substrates. The NMR studies on the Pd-π-allyl intermediates provide a deeper understanding about the effect of the ligand parameters on the origin of enantioselectivity. It also indicates that the nucleophilic attack takes place predominantly at the allylic terminal carbon atom located trans to the phosphite moiety.

Determination of the complete absolute configuration of petriellin A

We report the full structural determination of the depsipeptide petriellin A. The absolute configuration of the amino acid residues, N-methyl isoleucine and N-methyl threonine, have been determined by a combination of HPLC and TLC comparison of synthetic Marfey's derivatives and Marfey's derivatives of the natural product hydrolysate. The configuration of the chiral centres in these two N-methylated residues was found to be the same as those of the common unmethylated l-amino acids. CSIRO 2006.

New Dihydroxy Bis(Oxazoline) Ligands for the Palladium-Catalyzed Asymmetric Allylic Alkylation: Experimental Investigations of the Origin of the Reversal of the Enantioselectivity

The origin of the reversal of the enantioselectivity in the palladium-catalyzed allylic alkylation of rac-1,3-diphenyl-2-propenyl acetate with dimethyl malonate anion using chiral dihydroxy bis(oxazoline) "BO" ligands derived from (1S,2S)-(+)-2-amino-1-ph