74272-77-8

Basic information

• Product Name: (4S,5R)-4-methyl-2-phenyl-4,5-dihydrooxazole-4-carboxylic acid methyl ester
• CAS NO: 74272-77-8
• Molecular Weight: 219.24
• Mol File: 74272-77-8.mol
• Article Data: 10

Chemical Properties

• CAS DataBase Reference: (4S,5R)-4-methyl-2-phenyl-4,5-dihydrooxazole-4-carboxylic acid methyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: (4S,5R)-4-methyl-2-phenyl-4,5-dihydrooxazole-4-carboxylic acid methyl ester(74272-77-8)
• EPA Substance Registry System: (4S,5R)-4-methyl-2-phenyl-4,5-dihydrooxazole-4-carboxylic acid methyl ester(74272-77-8)

Safety Data

• Hazardous Substances Data: 74272-77-8(Hazardous Substances Data)

Upstream product

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

Downstream Products

• 88318-70-1 (4R,5R)-4,5-dimethyl-2-phenyl-4,5-dihydrooxazole-4-carboxylic acid methyl ester 
• 1040384-34-6 C₁₃H₁₇NO₂ 
• 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 
• 1383736-56-8 (4R,5S)-8-bromo-4,6-dimethyl-2-phenyl-3-oxa-1-azaspiro[4.4]nona-1,6-diene-7-carbaldehyde 
• 1397758-42-7 C₁₆H₂₀N₂O₅S 
• 1383736-54-6 1-((4R,5R)-5-methyl-4-(pent-4-en-1-yl)-2-phenyl-4,5-dihydrooxazol-4-yl)ethanone 
• 1383736-52-4 4-((4R,5R)-4-acetyl-5-methyl-2-phenyl-4,5-dihydrooxazol-4-yl)butanal 
• 1383736-67-1 C₂₄H₂₇NO₆ 
• 1383736-66-0 (4R,5S,7R)-8-(hydroxymethyl)-4,9-dimethyl-2-phenyl-3-oxa-1-azaspiro[4.4]nona-1,8-dien-7-ol 
• 1383736-65-9 (4R,5S,7R)-8-formyl-4,9-dimethyl-2-phenyl-3-oxa-1-azaspiro[4.4]nona-1,8-dien-7-yl benzoate 
• 1383736-63-7 (4R,5S,7S)-7-hydroxy-8-formyl-4,9-dimethyl-2-phenyl-3-oxa-1-azaspiro[4.4]nona-1,8-diene 

Relevant articles and documents

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.

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.