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A novel linking-protecting group strategy for solid-phase organic chemistry with configurationally stable alpha-[N-(phenylfluorenyl)]amino carbonyl compounds: Synthesis of enantiopure norephedrines on solid support

A novel linking strategy has been developed for synthesizing configurationally stable alpha-amino aldehyde on polymeric supports. Alkylation of L-alanine methyl ester with 9-bromo-9-p-bromophenylfluorenene, followed by ester hydrolysis and coupling to isoxazolidine, provided N-(9-p- bromophenylfluoren-9-yl)alanine isoxazolidide (5), which was transformed into its corresponding boronate 2 by a palladium-catalyzed cross-coupling reaction with diboron pinacol ester. Boronate 2 was anchored to four different polymeric aryl halides 6-9 in 70-99% yields. Polymer-bound alaninal 1b was then synthesized on non-cross-linked polystyrene by hydride reduction of isoxazolidide 10b. Treatment of alaninal 1b with phenylmagnesium bromide, cleavage of the resulting amino alcohol in a 1:2:2 TFA/CH2Cl2/anisole cocktail, and acylation with di-tert-butyl dicarbonate furnished N- (BOC)norephedrines 14 that were demonstrated to be enantiopure by conversion to diastereomeric thioureas 15 and analysis by HPLC. In summary, we have developed a process by which the 9-phenylfluoren-9-yl protecting group has been converted into a new linker for the solid-phase synthesis and manipulation of alpha-amino carbonyl compounds.

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Reference£º
Oxazolidine – Wikipedia,
Oxazolidine | C3H1285NO – PubChem

 

Discovery of Isoxazolidine hydrochloride

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39657-45-9, Name is Isoxazolidine hydrochloride, belongs to oxazolidine compound, is a common compound. Product Details of 39657-45-9In an article, once mentioned the new application about 39657-45-9.

Chirospecific Syntheses of Nitrogen and Side-Chain Modified Anatoxin Analogues. Synthesis of (1R)-Anatoxinal and (1R)-Anatoxinic Acid Derivatives

A straightforward and good yielding route to side-chain analogues of the potent neurotoxin and neurotransmitter (+)-anatoxin (1) has been developed.Peroxy acid oxidation of the (silyloxy)butadiene 43 derived from readily synthesized, optically pure (1R)-t-BOC-anatoxin (42) affords silyloxy ketone 44.Fluorolysis of 44 followed by oxidative cleavage of the resultant alpha-hydroxy ketone 45 gives a mixture of alpha,beta-unsaturated acid 46 and ester 41 in 57percent combined yield.Other approaches to these compounds, based on literature precedent, failed. (1R)-t-BOC-anatoxinic acid (46) then serves as educt for the synthesis of a wide variety of anatoxin derivatives with modified side-chain functionality.These analogues, designed to serve as probes of the antagonist binding site of the nicotinic acetylcholine receptor, include alcohol, aldehyde, amide, hydroxamate, and oxime ether functional groups.

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Oxazolidine – Wikipedia,
Oxazolidine | C3H1288NO – PubChem

 

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Amidinoureas

A new class of chemical compounds and their process of preparation is described. These compounds have valuable properties as anti-secretory, anti-spasmodic, anti-ulcerogenic and anti-diarrheal agents.

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Oxazolidine – Wikipedia,
Oxazolidine | C3H1259NO – PubChem

 

Top Picks: new discover of Isoxazolidine hydrochloride

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Reference of 39657-45-9, Because a catalyst decreases the height of the energy barrier, its presence increases the reaction rates of both the forward and the reverse reactions by the same amount.39657-45-9, Name is Isoxazolidine hydrochloride, molecular formula is C3H8ClNO. In a article£¬once mentioned of 39657-45-9

alpha-Amino Acids as Chiral Educts for Asymmetric Products. The Synthesis of alpha’-Amino-alpha,beta-ynones

alpha-Amino acid isoxazolidides have been developed as educts for the preparation of optically pure alpha’-amino-alpha,beta-ynones.The alpha-amino acids were first N-protected as their ethoxycarbonyl, tert-butoxycarbonyl, or phenylsulfonyl derivatives.The isoxazolidides then were formed by the simple, high yield acylation of isoxazolidine by in situ generated alpha-amino acid isobutyl carbonic anhydrides.Individual isoxazolidides of L-alpha-N-substituted alanine, phenylalanine, and methionine, when treated with lithium acetylide, lithium (trimethylsilyl)acetylide, or 1-hexynyllithium, gave high yields of the corresponding optically pure alpha,beta-acetylenic ketones.

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Oxazolidine – Wikipedia,
Oxazolidine | C3H1282NO – PubChem

 

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Synthesis of anisolylated aspartyl and glutamyl tripeptides

A process has been developed for transforming the beta-carboxyl of aspartate and the gamma-carboxyl of glutamate into anisolyl ketones. These ketones are occasional byproducts in peptide synthesis, resulting from deprotection or resin-removal processes in the presence of anisole as a scavenger. The ketone amino acids have been incorporated in a tripeptide by coupling with CBMIT. During peptide bond formation the keto group of the glutamyl residue required protection, which was provided as the ethylene dithioketal.

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Oxazolidine – Wikipedia,
Oxazolidine | C3H1275NO – PubChem

 

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The alpha-effect in cyclic secondary amines: new scaffolds for iminium ion accelerated transformations

Five-membered secondary amine heterocycles containing an alpha-heteroatom were prepared and shown to be ineffective as catalysts for the iminium ion catalysed Diels-Alder reaction between cinnamaldehyde and cyclopentadiene. Their six-membered counterparts proved to be highly active catalysts. In stark contrast, the catalytic activity observed when comparing the non alpha-heteroatom cyclic amines proline methyl ester and methyl pipecolinate showed the five-membered ring amine was significantly more active. Concurrent density functional theoretical calculations suggest a rationale for the observed trends in reactivity, highlighting that LUMO activation through an iminium ion intermediate plays a key role in catalytic activity.

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Oxazolidine – Wikipedia,
Oxazolidine | C3H1279NO – PubChem

 

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Synthesis and antimicrobial activity of 4H-4-oxoquinolizine derivatives: Consequences of structural modification at the C-8 position

The antibacterial 4H-4-oxoquinolizines were introduced recently to overcome bacterial resistance to fluoroquinolones. They exhibit potent antibacterial activity against Gram-positive, Gram-negative, and anaerobic organisms and are highly active against some quinolone-resistant bacteria including quinolone-resistant MRSA. Preliminary studies indicated that oxoquinolizines possess distinct activity and toxicity profiles as compared with their parent quinolones. In order to develop a potent antibacterial agent with the desired spectrum of activity, good tolerability, and balanced pharmacokinetic profile, we synthesized and evaluated a series of oxoquinolizines with various substituents at the C-8 position. Most compounds tested in this study demonstrated better activity against Gram-positive bacteria than ciprofloxacin and exhibited good susceptibility against ciprofloxacin- and methicillin-resistant S. aureus. While maintaining potent in vitro activity, several compounds showed improved in vivo efficacy over ABT-719 as indicated by the mouse protection test. As an example, the oral ED50 values for the cis-3-amino-4-methylpiperidine analogue 3ss against S. aureus NCTC 10649M, S. pneumoniae ATCC 6303, and E. coli JUHL were 0.8, 2.0, and 1.4 mg/kg, compared to 3.0, 10.0, and 8.3 mg/kg for ABT-719. The current study revealed that the steric and electronic environment conformation, and absolute stereochemistry of the C-8 group are very important to the antibacterial profiles. Structural modifications of the C-8 group provide a useful means to improve the antibacterial activities, physicochemical properties, and pharmacokinetic profiles. Manipulation of the C-8 group also allows us to generate analogues with the desired spectrum of activity, such as analogues that are selective against respiratory pathogens.

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Oxazolidine – Wikipedia,
Oxazolidine | C3H1290NO – PubChem

 

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THE REACTION OF AMINES WITH PHTALIMIDE DERIVATIVES. A CONVENIENT SYNTHESIS OF ISOXAZOLIDINE

The reaction of tert-butylamine, isoxazolidine and hydrazine with N-<(3-chloropropyl)oxy>phtalimide is investigated.A convenient synthesis of oxazolidine is described.

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Reference£º
Oxazolidine – Wikipedia,
Oxazolidine | C3H1278NO – PubChem

 

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A herbicide wicked grass ether original medicine and its preparation method (by machine translation)

This invention relates to a herbicide wicked grass ether original medicine and its preparation method, which belongs to the technical field of agricultural chemical raw material, its preparation process is as follows: in order to 2 – (4 – hydroxy-phenoxy) propionic acid, 2, 3, 5 – trichloro-pyridine as raw materials in organic solvent A, alkali A and catalyst A etherification reaction under the conditions of the synthesis of the key intermediate (R, S) – 2 – (4 – ((3, 5 – dichloro pyridine – 2 – yl) oxy) phenoxy) propionic acid, the intermediate and oxalyl reaction preparation (R, S) – 2 – (4 – ((3, 5 – dichloro pyridine – 2 – yl) oxy) phenoxy) propionyl chloride, finally with the Isoxazolidine hydrochloride in alkali B, catalyst B and organic solvent B carry out the esterification reaction under the conditions of the original drug preparation wicked grass ether. In the preparation method, and is simple, synthesis is easy to operate, easy post treatment, low requirements on equipment, has a relatively high content and yield. (by machine translation)

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Reference£º
Oxazolidine – Wikipedia,
Oxazolidine | C3H1274NO – PubChem

 

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CYCLIC IMINOPEPTIDE DERIVATIVES

The invention concerns antibacterial cyclic iminopeptide derivatives, methods for producing same, use thereof for treating and/or preventing diseases, as well as their use for producing drugs for treating and/or preventing diseases, in particular bacterial infections.

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Reference£º
Oxazolidine – Wikipedia,
Oxazolidine | C3H1264NO – PubChem