60538-17-2

Upstream product

• 60538-16-1 (2R,3S)-N-benzoylthreonine methyl ester 
• 906324-06-9 N-benzoyl-D_s-threonine 
• 75-07-0 acetaldehyde 
• 39994-75-7 L-threonine methyl ester hydrochloride 
• 7471-86-5 methyl benzimidate 
• 3373-59-9 L-threonine methyl ester 
• 5333-86-8 ethyl benzimidate hydrochloride 
• 60143-52-4 L-threonine methyl ester hydrochloride 
• 79893-89-3 N-benzoyl-L-threonine methyl ester 
• 267653-05-4 N-benzoyl-(2S,3S)-threonine methyl ester 
• 65-85-0 benzoic acid 

Downstream Products

• 24830-94-2 D-allo-threonine 
• 78508-98-2 lithium (2S,3R)-2,3-(N,O-benzylidyne)-2-amino-3-hydroxy-butyrate 
• 922179-52-0 (4R,5R)-2-(5-methyl-2-phenyl-4,5-dihydrooxazol-4-yl)-1,3-diphenyl-propan-2-ol 
• 100063-41-0 methyl 5-methyl-2-phenyloxazole-4-carboxylate 
• 88318-70-1 (4R,5R)-4,5-dimethyl-2-phenyl-4,5-dihydrooxazole-4-carboxylic acid methyl ester 
• 26927-54-8 (E)-α-N-benzoylamino-2-butenoic acid methylester 
• 60027-58-9 (Z)-α-N-benzoylamino-2-butenoic acid methylester 
• 88318-74-5 (4S,5S)-4-Isopropyl-5-methyl-2-phenyl-4,5-dihydro-oxazole-4-carboxylic acid methyl ester 
• 88318-73-4 (4S,5S)-5-Methyl-4-(3-methyl-butyl)-2-phenyl-4,5-dihydro-oxazole-4-carboxylic acid methyl ester 
• 88318-69-8 (4S,5S)-4,5-Dihydro-4,5-dimethyl-2-phenyloxazol-4-carbonsaeure-methylester 
• 88318-71-2 (4S,5S)-4-Ethyl-4,5-dihydro-5-methyl-2-phenyloxazol-4-carbonsaeure-methylester 
• 1383736-68-2 C₂₄H₂₇NO₇ 
• 1383736-55-7 (4R,5S)-4,6-dimethyl-2-phenyl-3-oxa-1-azaspiro[4.4]nona-1,6-diene-7-carbaldehyde 

Relevant academic research and scientific papers

Synthesis of the Siderophore Coelichelin and Its Utility as a Probe in the Study of Bacterial Metal Sensing and Response

A convergent total synthesis of the siderophore coelichelin is described. The synthetic route also provided access to acetyl coelichelin and other congeners of the parent siderophore. The synthetic products were evaluated for their ability to bind ferric iron and promote growth of a siderophore-deficient strain of the Gram-negative bacterium Pseudomonas aeruginosa under iron restriction conditions. The results of these studies indicate coelichelin and several derivatives serve as ferric iron delivery vehicles for P. aeruginosa.

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.

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.

Method for enantioselective hydrogenation of chromenes

A method for preparing an enantiomeric chromane, by asymmetrically hydrogenating a chromene compound in the presence of an Ir catalyst having a chiral ligand. The method includes the enantioselective preparation of enantiomeric equol. A preferred Ir catalyst has a chiral phosphineoxazoline ligand. Enantiomeric chromanes of high stereoselective purity can be obtained.

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

Functionalised 2,3-dimethyl-3-aminotetrahydrofuran-4-one and N-(3-oxo-hexahydrocyclopenta[b]furan-3a-yl)acylamide based scaffolds: Synthesis and cysteinyl proteinase inhibition

A stereoselective synthesis of functionalised (2R,3R)-2,3-dimethyl-3- amidotetrahydrofuran-4-one, its (2S,3R)-epimer and (3aR,6aR)-N-(3-oxo- hexahydrocyclopenta[b]furan-3a-yl)acylamide cysteinyl proteinase inhibitors has been developed using Fmoc-protected scaffolds 6-8 in a solid-phase combinatorial strategy. Within these scaffolds, the introduction of an alkyl substituent α to the ketone affords chiral stability to an otherwise configurationally labile molecule. Preparation of scaffolds 6-8 required stereoselective syntheses of suitably protected α-diazomethylketone intermediates 9-11, derived from appropriately protected α-methylthreonines (2R,3R)-12, (2R,3S)-13 and a protected analogue of (1R,2R)-1-amino-2- hydroxycyclopentanecarboxylic acid 14. Application of standard methods for the preparation of amino acid α-diazomethylketones, through treatment of the mixed anhydride or pre-formed acyl fluorides of intermediates 12-14 with diazomethane, proved troublesome giving complex mixtures. However, the desired α-diazomethylketones were isolated and following a lithium chloride/acetic acid promoted insertion reaction provided scaffolds 6-8. Elaboration of 6-8 on the solid phase gave α,β-dimethyl monocyclic ketone based inhibitors 38a-f, 39a,b,d,e,f and bicyclic inhibitors 40a-e that exhibited low micromolar activity against a variety of cysteinyl proteinases.

Materials and methods for the treatment of diabetes, hyperlipidemia, hypercholesterolemia, and atherosclerosis

The subject invention provides pharmaceutical compounds useful in the treatment of Type II diabetes. These compounds are advantageous because they are readily metabolized by the metabolic drug detoxification systems. Particularly, thiazolidinedione analogs that have been designed to include esters within the structure of the compounds are provided. This invention is also drawn to methods of treating disorders, such as diabetes, comprising the administration of therapeutically effective compositions comprising compounds that have been designed to be metabolized by serum or intracellular hydrolases and esterases. Pharmaceutical compositions of the ester-containing thiazolidinedione analogs are also taught.

Benzamide bioisosteres incorporating dihydroheteroazole substructures: EPC synthesis and SAR leading to a selective dopamine D4 receptor partial agonist (FAUC 179)

Conformationally restricted benzamide bioisosteres were investigated when the chiral phenyldihydroimidazole derivative 4e (FAUC 179) showed strong and highly selective dopamine D4 receptor binding (Kihigh = 0.95 nM). Mitogenesis experiments indicated partial agonist properties (42%). EPC syntheses of the target compounds of type 4 were performed starting from α-amino acids.

Synthese d'oxazolines insaturees isomeres a partir d'aminoalcools chiraux en vue du greffage sur silice

Synthesis of unsaturated oxazoline isomers from chiral amino alcohols for bonding to silica.In order to study their enantioselective ability, four chiral unsaturated oxazoline isomers were synthesized from (1S,2S)-2-amino-1-phenylpropane-1,3-diol and (2S,3R)-2-amino-3-hydroxybutanoic acid (S-threonine).A terminal double bond was introduced on these structures in order to be able to graft them onto silica and access chiral stationary phases for chromatography. - Keywords: chiral unsaturated oxazoline; heterocyclization; selective reaction; grafted silica