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A new methodology for the synthesis of beta-amino acids

A differentially functionalized succinic acid unit 6 undergoes alkylation with excellent regio- and high stereocontrol at the carbon alpha to the imide to furnish the alkylated product 7 in 60-83% yield. Selective removal of the imide provides 8 in 80-90% yields. Curtius rearrangement of 8 with retention of stereochemistry provides N-protected beta-amino acids (9) in 70-83% yields. Alternatively, selective deprotection of the ester group followed by Curtius rearrangement provides isomeric beta-amino acids 14a, 14b, and 14e in good yields. The methodology has been successfully applied to the synthesis of N-Boc-iturinic acid and 2-methyl-3-aminopropanoic acid, components of the antifungal peptide iturin and the cytotoxic depsipeptide cryptophycin respectively.

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Oxazolidine – Wikipedia,
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The important role of 102029-44-7

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Diastereoselective synthesis of fused lactone-pyrrolidinones; Application to a formal synthesis of (-)-salinosporamide a

A mild, diastereoselective synthesis of fused lactone-pyrrolidinones using an oxidative radical cyclization is reported. The methodology is demonstrated in a formal synthesis of (-)-salinosporamide A.

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Extended knowledge of 5,5-Dimethyloxazolidine-2,4-dione

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Photographic yellow dye-forming couplers

A photographic element comprises a light sensitive silver halide emulsion layer having associated therewith an open chain alpha-carbonyl acetanilide yellow dye-forming coupler having the formula: wherein R1is selected from the group consisting of alkyl, aryl, heterocyclic, and amino groups, provided that R1may form a ring bonded to another carbon atom which is a member of Ring “A”; each R2is independently selected from the group consisting of those substituents having a Hammett’s sigma value of 0 or less, and m is from 0 to 4; each R3and R4for each of the n carbon atoms is independently selected from the group consisting of hydrogen, alkoxy, aryl, heterocyclic, aryloxy, and alkyl groups, and n is 0 to 16; each R5independently selected from the group consisting of amino, alkyl groups, and groups linked to the “B” ring by oxygen or sulfur, and p is 1 to 3, provided that two R5groups may join to form a ring; R6is selected from the group consisting of alkyl, aryl, and amino groups; each L is independently a divalent linking group and q is 0 to 3; and Ring “A” is bonded indirectly to the 3-, 4-, or 5-position of Ring “B”; and Z is hydrogen, or a group capable of coupling-off when the coupler reacts with an oxidized color developing agent.

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Archives for Chemistry Experiments of (R)-4-Benzyl-2-oxazolidinone

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Oxazolidinone penetration enhancing compounds

Compositions for carrying physiologically active agents through body membranes having the structural formula I: STR1 where: R=H, Alkyl group containing from 1-18 carbon atoms, cycloalkyl, aryl, aralkyl, alkoxy, hydroxyalkyl, alkoyloxyalkyl, acyloxyalkyl and alkoxyalkyl; X=O and NR1, where R1 is selected from H, alkyl, aralkyl acyl group containing from 1-18 carbon atoms, cycloalkyl, hydroxyalkyl, alkoyloxyalkyl acyloxyalkyl and alkoxyalkyl; Y=O and NR2, where R2 is selected from H, alkyl, aralkyl, cycloalkyl, acyl group containing from 1-18 carbon atoms, hydroxyalkyl, alkoyloxyalkyl, acyloxyalkyl and alkoxyalkyl; m=2-4; and n=0-4, are disclosed.

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Discovery of (R)-4-Benzyl-2-oxazolidinone

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Chiral electrophilic ‘glycinal’ equivalents. New synthons for optically active alpha-amino acids and 4-substituted 2-oxazolidinones

The thermal reaction of 3-[(1S)-2-alkoxy-1-apocamphanecarbonyl]-2-oxazolones (21a-c) with dialkyl azodicarboxylates (9) results in exclusive formation of [4 + 2] type cycloadducts (22 and 23) with moderate levels of diastereofacial selection (up to 72% d.e.). The diastereomers thus obtained were readily purified and subsequent treatment with acidic methanol followed by removal of the auxiliary with LiBH4/MeOH (1:2) gave optically pure 4-methoxy-5-hydrazino-2-oxazolidinones (26 and 27), which serve as alpha-aminoaldehyde templates useful for the synthesis of a wide variety of optically active alpha-amino acids as well as 4-alkyl and 4-aryl-2-oxazolidinones.

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The Absolute Best Science Experiment for 3190-70-3

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New amphiphilic biodegradable beta-cyclodextrin/poly(l-leucine) copolymers: Synthesis, characterization, and micellization

A new amphiphilic biodegradable beta-cyclodextrin/poly(l-leucine) (beta-CD-PLLA) copolymer was synthesized by ring-opening polymerization of N-carboxy-l-alanine anhydride (LL-NCA) in N,N-dimethylformamide (DMF) initiated by mono-6-amino-beta-cyclodextrin (H2N-beta-CD). The structures of the copolymers were determined by IR, 1H NMR and GPC. The fluorescence technique was used to determine the critical micelle concentrations (CMC) of copolymer micelle solution. The diameter and distribution of micelles were characterized by dynamic light scattering (DLS) and its shape was observed by transmission electron microscopy (TEM). The results showed that LL-NCA could be initiated by H2N-beta-CD to produce the copolymer. These copolymers could self-assemble into nano-micelles in water. The CMC of copolymer solution and the size of micelle reduced with increasing proportion of the hydrophobic part. TEM images demonstrated the micelles are all spherical. Such block copolymers could be expected to find applications in drug delivery systems and other biomedical fields.

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Facile formation of N-acyl-oxazolidinone derivatives using acid fluorides

A mild method is presented for the formation of N-acylated oxazolidinones that employs acid fluorides and mild bases, such as iPr 2NEt and NEt3. Optimized reaction conditions for two types of substrates have been developed utilizing either the oxazolidinone itself or the corresponding in situ generated O-silyloxazolidinones resulting in the formation of the desired N-acylated products in high yields of up to 98%.

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More research is needed about (4S,5R)-4-Methyl-5-phenyloxazolidin-2-one

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POLYUNSATURATED FATTY ACIDS FOR THE TREATMENT OF DISEASES RELATED TO CARDIOVASCULAR, METABOLIC AND INFLAMMATORY DISEASE AREAS

The present disclosure relates to lipid compounds of the general formula (I): R1-O-C(R2)(R3) -X (I) wherein R1 is a C10-C22 alkyl group, a C10-C22 alkenyl group having 1-6 double bonds, or a C10-C22 alkynyl group having 1-6 triple bonds; R2 and R3 are the same or different and may be chosen from different substituents; and X is a carboxylic acid or a derivative thereof, such as a carboxylic ester, a carboxylic anhydride, a phospholipid, triglyceride, or a carboxamide; or a pharmaceutically acceptable salt, solvate, solvate of such salt or a prodrug thereof. The present disclosure also relates to pharmaceutical compositions and lipid compositions comprising at least one compound according to the present disclosure, and to such compounds for use as medicaments or for use in therapy, in particular for the treatment of diseases related to the cardiovascular, metabolic, and inflammatory disease area.

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New explortion of Oxazolidin-2-one

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Rhodium-catalyzed asymmetric cycloisomerization of 1,6-ene-ynamides

The rhodium-catalyzed asymmetric cycloisomerization of heteroatom-bridged 1,6-ene-ynamides proceeded to give high yields of functionalized 3-aza- and oxabicyclo[4.1.0]heptene derivatives with high enantioselectivity, which was achieved by use of a rhodium/chiral diene catalyst. The 1,6-ene-ynamides substituted with 2-oxazolidinone and 2-azetidinone moieties at the alkyne terminus were found to display high reactivity towards the rhodium/chiral diene catalyst, where the chelate coordination of the alkyne moiety and the carbonyl oxygen of the ene-ynamides might be responsible for the high catalytic activity. Copyright

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Can You Really Do Chemisty Experiments About 173604-33-6

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METHOD OF PRODUCING BERAPROST

An improved method is described for making single isomers of synthetic benzoprostacyclin analogue compounds, in particular the pharmacologically active 314-d isomer of beraprost. In contrast to the prior art, the method is stereoselective and requires fewer steps than the known methods for making these compounds.

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