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Multiple labeling of a potent CX3CR1 antagonist for the treatment of multiple sclerosis

Several methods for the preparation of five isotopologues of the CX 3CR1 antagonist 1 were developed. Volatile and radioactive 1-chloro- and 1-bromo-ethyl-benzene was handled in [2?-14C] and [3?, 5?-3H] labeling of 1. d-Leucinol ((R)-2-amino-4-methylpentan-1-ol) was labeled as [1-14C] and [4- 14C] via a Wittig reaction using Garner’s aldehyde and a Strecker amino acid synthesis with d-acylase resolvation, respectively. A [ 2H10]d-leucinol was used for the stable labeled [M + 10] isotopologue. The products were isolated with 97.6-100% stereo chemical and radiochemical purity as for specific activity 768 GBq/mmol and 1.6-2.0 GBq/mmol, respectively. Five isotopologues of the CX3CR1 antagonist 1 were developed. Volatile and radioactive 1-chloro- and 1-bromo-ethyl-benzene was handled in [2?-14C] and [3?, 5?-3H] labeling of 1. d-Leucinol was labeled as [1-14C] and [4- 14C] via a Wittig reaction using Garner’s aldehyde and a Strecker amino acid synthesis with d-acylase resolvation, respectively. A [ 2H10]d-leucinol was used for the stable labeled [M + 10] isotopologue. Copyright

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Oxazolidine – Wikipedia,
Oxazolidine | C3H2534NO – PubChem

 

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A concise synthesis of (2 S,3 S,4 S)-2-(hydroxymethyl)pyrrolidine-3,4-diol (LAB1)

The synthesis of (2S,3S,4S)-2-(hydroxymethyl)pyrrolidine-3,4-diol (LAB1) from Garners aldehyde is described using the Sharpless asymmetric dihydroxylation as the key step. Georg Thieme Verlag Stuttgart – New York.

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Oxazolidine – Wikipedia,
Oxazolidine | C3H2555NO – PubChem

 

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COMPOUNDS COMPRISING A CYCLOBUTOXY GROUP

The present invention relates to compounds comprising a cyclobutoxy group, processes for preparing them, pharmaceutical compositions comprising said compounds and their use as pharmaceuticals.

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Oxazolidine – Wikipedia,
Oxazolidine | C3H2470NO – PubChem

 

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NEW COMPOUNDS

The invention provides compounds of the formula I wherein Q is aryl or heterocyclyl any of which is optionally substituted; Z is O, S, NRa or S(=O)p; Y is NH, NHNH, CH2NH, O, S or S(=O)p; n is 0, 1, 2 or 3; m is 0, 1 or 2; p is 1 or 2; Ra is H or C1-C4alkyl; R1 is hydrogen, C1-C6alkyl, C0-C3alkanediylC3-C7cycloalkyl, C0-C3alkanediylaryl or C0- C3alkanediylheterocyclyl; R2 is hydrogen or C1-C6alkyl; X’ is hydrogen, fluoro, hydroxy, amino or C1-C6alkoxy; X” is hydrogen, or when X’ is fluoro, then X” may also be fluoro; R3is C1-C6alkyl; R4′ is C1-C6alkyl; R4″ is H or C1-C6alkyl; or R4′ and R4″ together with the carbon atom to which they are attached define a C3-C6cycloalkyl; W is C1-C6alkyl, C3-C7cycloalkyl, aryl or heterocyclyl any of which is optionally substituted; or a pharmaceutically acceptable salt, hydrate or N-oxide thereof. The compounds of the invention are inhibitors of aspartyl proteases such as renin and are among other things useful for the treatment of conditions associated with activities of the RAS, such as hypertension, heart failure and renal insufficiency. ”

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Oxazolidine – Wikipedia,
Oxazolidine | C3H2468NO – PubChem

 

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A straightforward preparation of chiral 5-(aminomethyl)oxazole derivatives from alpha-amino esters and alpha-lithiated isocyanides

An efficient and general preparation of several chiral N-protected 5- (aminomethyl)oxazoles has been accomplished by treatment of N-protected alpha- amino esters with alpha-lithiated isocyanides, obtained by metalation of methyl and benzyl isocyanides with BuLi or of ethyl isocyanide with lithium diisopropylamide.

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Oxazolidine – Wikipedia,
Oxazolidine | C3H2544NO – PubChem

 

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Efficient synthesis of a configurationally stable L-serinal derivative

An efficient synthesis of a configurationally stable L-serinal derivative 8 was achieved using an N-hydroxymethyl group in about 50% overall yield in four steps from L-serine. Not more than 1% racemization was observed during the preparation of 8. Its enantiomeric integrity was maintained for at least 15 days at room temperature, and it was stable on silica gel. The orthogonal protective groups of 8 would make it a useful chiral synthon.

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Oxazolidine – Wikipedia,
Oxazolidine | C3H2564NO – PubChem

 

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Related Products of 95715-86-9, Chemistry is the science of change. But why do chemical reactions take place? Why do chemicals react with each other? The answer is in thermodynamics and kinetics.In a document type is Article, and a compound is mentioned, 95715-86-9, Methyl (R)-N-Boc-2,2-dimethyloxazolidine-4-carboxylate, introducing its new discovery.

Synthesis of Nontoxic Fluorous Sphingolipids as Molecular Probes of Exogenous Metabolic Studies for Rapid Enrichment by Fluorous Solid Phase Extraction

Fluorous solid-phase extraction (FSPE) is a useful technique for efficient selective enrichment of fluorous compounds from nonfluorous molecules. Sphingolipids and their metabolites, which are ubiquitous building blocks of eukaryotic and prokaryotic cell membranes, play crucial roles, for example, as signaling molecules. However, details of the functions and metabolic mechanisms of exogenous sphingolipids have remained unknown compared with those of their endogenous analogs. To better understand these unknown roles, chemical probes with appropriate biological and physicochemical properties are needed. In this study, we designed and synthesized new fluorous sphingolipids to reveal these roles. Furthermore, we confirmed that they could be efficiently and rapidly separated from normal sphingolipids by FSPE, and that they hardly showed any cytotoxic activity, similarly to normal sphingolipids at the same dose. We also showed that these fluorinated ceramides could act as metabolic substrates for sphingomyelin synthase 2 (SMS2). This demonstrates their potential for further biological studies.

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Oxazolidine – Wikipedia,
Oxazolidine | C3H2553NO – PubChem

 

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The Synthesis and Configurational Stability of Differentially Protected beta-Hydroxy-beta-amino Aldehydes

Syntheses of 1,1-dimethylethyl (S)-4-formyl-2,2-dimethyl-3-oxazolidinecarboxylate (5) and 1,1-dimethylethyl (4S-trans)-4-formyl-2,2,5-trimethyl-3-oxazolidinecarboxylate (6) from commercially available serine and threonine derivatives are described.The method involves selective reduction of the corresponding oxazolidine esters 3 and 4 using diisobutylaluminum hydride at low temperature.These differentially protected beta-hydroxy-alpha-amino aldehydes are also shown to be produced in 93-95 percent enantiomeric excess (via NMR and HPLC analysis of the Mosher esterderivatives 8 and epi-8)-thus making them useful as chiral, nonracemic synthons for asymmetric synthesis.

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Oxazolidine – Wikipedia,
Oxazolidine | C3H2514NO – PubChem

 

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Total Synthesis of the Post-translationally Modified Polyazole Peptide Antibiotic Goadsporin

The structurally unique polyazole antibiotic goadsporin contains six heteroaromatic oxazole and thiazole rings integrated into a linear array of amino acids that also contains two dehydroalanine residues. An efficient total synthesis of goadsporin is reported in which the key steps are the use of rhodium(II)-catalyzed reactions of diazocarbonyl compounds to generate the four oxazole rings, which demonstrates the power of rhodium carbene chemistry in organic chemical synthesis.

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Oxazolidine – Wikipedia,
Oxazolidine | C3H2504NO – PubChem

 

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Capturing Intermediates in the Reaction Catalyzed by NosN, a Class C Radical S-Adenosylmethionine Methylase Involved in the Biosynthesis of the Nosiheptide Side-Ring System

Nosiheptide is a ribosomally synthesized and post-translationally modified thiopeptide natural product that possesses antibacterial, anticancer, and immunosuppressive properties. It contains a bicyclic structure composed of a large macrocycle and a unique side-ring system containing a 3,4-dimethylindolic acid bridge connected to the side chains of Glu6 and Cys8 of the core peptide via ester and thioester linkages, respectively. In addition to the structural peptide, encoded by the nosM gene, the biosynthesis of the side-ring structure requires the actions of NosI, -J, -K, -L, and -N. NosN is annotated as a class C radical S-adenosylmethionine (SAM) methylase, but its true function is to transfer a C1 unit from SAM to C4 of 3-methyl-2-indolic acid (MIA) with concomitant formation of a bond between the carboxylate of Glu6 of the core peptide and the nascent C1 unit. However, exactly when NosN performs its function during the biosynthesis of nosiheptide is unknown. Herein, we report the syntheses and use of three peptide mimics as potential substrates designed to address the timing of NosN’s function. Our results show that NosN clearly closes the side ring before NosO forms the pyridine ring and most likely before NosD/E catalyzes formation of the dehydrated amino acids, although the possibility of a more random process (i.e., NosN acting after NosD/E) cannot be ruled out. Using a substrate mimic containing a rigid structure, we also identify and characterize two reaction-based adducts containing SAM fused to C4 of MIA. The two SAM adducts are derived from a consensus radical-containing species proposed to be the key intermediate – or a derivative of the key intermediate – in our proposed catalytic mechanism of NosN.

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Reference£º
Oxazolidine – Wikipedia,
Oxazolidine | C3H2557NO – PubChem