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Solution-phase automated synthesis of an alpha-amino aldehyde as a versatile intermediate

A solution-phase automated synthesis of the versatile synthetic intermediate, Garner’s aldehyde, was demonstrated. tert-Butoxycarbonyl (Boc) protection, acetal formation, and reduction of the ester to the corresponding aldehyde were performed utilizing our originally developed automated synthesizer, ChemKonzert. The developed procedure was also useful for the synthesis of Garner’s aldehyde analogues possessing fluorenylmethyloxycarbonyl (Fmoc) or benzyloxycarbonyl (Cbz) protection.

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Reference:
Oxazolidine – Wikipedia,
Oxazolidine | C3H2536NO – PubChem

 

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Telomestatin: Formal total synthesis and cation-mediated interaction of its seco-derivatives with G-quadruplexes

The structurally unique natural product telomestatin incorporates seven oxazole rings and one sulfur-containing thiazoline in a macrocyclic arrangement. The compound is a potent inhibitor of the enzyme telomerase and therefore provides a structural framework for developing new potential therapeutic agents for cancer. An efficient formal total synthesis of telomestatin is reported in which the key steps are the use of dirhodium-(II)-catalyzed reactions of diazocarbonyl compounds to generate six oxazole rings, demonstrating the power of rhodium carbene methodology in organic chemical synthesis. CD spectroscopy establishes that seco-derivatives of telomestatin are potent stabilizers of G-quadruplex structures derived from the human telomeric repeat sequence. Mass spectrometry studies, confirmed by molecular dynamics simulations, provide the first evidence that high affinity binding to terminal G-tetrads in both 1:1 and 2:1 ligand complexes is mediated through the macrocycle coordinating a monovalent cation, with selectivity for the antiparallel structure.

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Reference:
Oxazolidine – Wikipedia,
Oxazolidine | C3H2532NO – PubChem

 

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Synthesis of 2-isoxazoline and alpha-hydroxy ketomethylene dipeptide isosteres

We have developed a simple and stereoselective method for synthesizing novel dipeptide isosteres using nitrile oxide cycloaddition as a key reaction. Employing this method, we have prepared efficiently various peptidomimetics containing 2-isoxazolines and alpha-hydroxy ketomethylene dipeptide isosteres.

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Reference:
Oxazolidine – Wikipedia,
Oxazolidine | C3H2500NO – PubChem

 

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Catalytic Enantioselective Direct Aldol Addition of Aryl Ketones to alpha-Fluorinated Ketones

The catalytic enantioselective synthesis of alpha-fluorinated chiral tertiary alcohols from (hetero)aryl methyl ketones is described. The use of a bifunctional iminophosphorane (BIMP) superbase was found to facilitate direct aldol addition by providing the strong Br¡ãnsted basicity required for rapid aryl enolate formation. The new synthetic protocol is easy to perform and tolerates a broad range of functionalities and heterocycles with high enantioselectivity (up to >99:1 e.r.). Multi-gram scalability has been demonstrated along with catalyst recovery and recycling. 1H NMR studies identified a 1400-fold rate enhancement under BIMP catalysis, compared to the prior state-of-the-art catalytic system. The utility of the aldol products has been highlighted with the synthesis of various enantioenriched building blocks and heterocycles, including 1,3-aminoalcohol, 1,3-diol, oxetane, and isoxazoline derivatives.

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Reference£º
Oxazolidine – Wikipedia,
Oxazolidine | C3H2489NO – PubChem

 

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Synthesis of D-erythro-sphingosine and D-erythro sphinganine via 3- ketosphinganine

D-erythro- sphingosine and D-erythro-sphinganine can be produced in protected form from serine by a synthetic approach in which the normal biological intermediate 3-ketosphinganine in protectyed form, is a key synthetic intermediate. The sequence is short and convergent, proceeds in good overall yields (? 30% for 6 steps) and with excellent stereocontrol (>91% de, >95% ee).

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Oxazolidine – Wikipedia,
Oxazolidine | C3H2520NO – PubChem

 

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Novel aliphatic compounds, process for their preparation and their usage

The present invention provides an aliphatic compound represented by the following formula (I) or pharmacologically acceptable salts thereof: 1 where n denotes an integer of 1 to 11, and 1 denotes an integer of 1 to 16,the aliphatic compound being an optical isomer of the (2R,3S,2?S) configuration when the 8-position thereof is a double bond, or an optical isomer of the (2S,3R,2?RS) configuration when the 8-position is a single bond; methods for producing the compound or pharmacologically acceptable salts thereof; and uses of the compound in the treatment of cardiovascular diseases (e.g. arteriosclerosis, cardiac diseases), cancer, rheumatism, diabetic retinopathy, and respiratory diseases.

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Reference£º
Oxazolidine – Wikipedia,
Oxazolidine | C3H2482NO – PubChem

 

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Synthesis of new trans double-bond sphingolipid analogues: Delta4,6 and Delta6 ceramides

Unsaturation was introduced at Delta4,6 and Delta6 of the sphingoid chain of naturally occurring ceramide 1 via a beta-keto sulfoxide (12) and sulfone (18) derived from N-Boc-L-serine methyl ester acetonide (9), affording two novel ceramide analogues, (2S,3R)-2-octanoylamidooctadeca-(4E,6E)-diene-1,3diol (2) and (2S,3R)-2-octanoylamidooctadec-(6E)-ene-1,3-diol (3). After C-alkylation of 12 with (E)1-bromo-2-tetradecene (8), a trans double bond was installed by elimination of PhS(O)H, providing conjugated dienone oxazolidine 13. Reaction of 18 with 8, followed by desulfonation (Al(Hg)), afforded keto-oxazolidine 20, which bears a (E)-Delta6 double bond. The syntheses of analogues 2 and 3 from ketones 13 and 20, respectively, were completed by the following sequence of reactions: diastereoselective reduction (NaBH4/CeCl3 or DIBAL-H), hydrolysis of the oxazolidine ring, liberation of the amino group, and installation of the N-amide group.

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Reference£º
Oxazolidine – Wikipedia,
Oxazolidine | C3H2499NO – PubChem

 

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IOOC route to substituted chiral pyrrolidines. Potential glycosidase inhibitors

Branched-chain five-membered ring aza-sugar analogues, synthesized from amino acids by an intramolecular oxime-olefin cycloaddition reaction, the IOOC route, were found to be selective glycosidase inhibitors. The derivative 2,4(S)-di(hydroxymethyl)-3(S)-aminopyrrolidine, obtained from D-serine, was about 1 order of potency more active than its enantiomer obtained from L- serine.

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Oxazolidine – Wikipedia,
Oxazolidine | C3H2511NO – PubChem

 

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In heterogeneous catalysis, the catalyst is in a different phase from the reactants. COA of Formula: C12H21NO5, At least one of the reactants interacts with the solid surface in a physical process called adsorption in such a way. 95715-86-9, name is Methyl (R)-N-Boc-2,2-dimethyloxazolidine-4-carboxylate. In an article£¬Which mentioned a new discovery about 95715-86-9

BISPHENYL COMPOUNDS USEFUL AS VITAMIN D3 RECEPTOR AGONISTS

The present invention discloses bisphenyl compounds of the formula (I): wherein R1, R2, R3, R4, R5, R6, X, Y, W are defined herein after. These compounds are useful as pharmaceuticals.

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Reference£º
Oxazolidine – Wikipedia,
Oxazolidine | C3H2486NO – PubChem

 

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2-Thiazolyl alpha-amino ketones: A new class of reactive intermediates for the stereocontrolled synthesis of unusual amino acids

The thiazole-based one carbon homologation of four alpha-amino acids (L-phenylalanine, L-leucine, L-threonine, and L-serine) to the corresponding alpha-hydroxy beta-amino aldehydes and acids in both configurations at C(alpha), is described. The methodology involves the following key operations: (i) the conversion of an alpha-amino ester to a 2-thiazolyl alpha-amino ketone; (ii) the stereocontrolled reduction of a ketone carbonyl to either syn or anti alpha,beta-amino alcohols; (iii) the aldehyde release from the thiazole ring; (iv) the oxidation of the aldehyde to a carboxylic acid. The methodology was only partially applied to L-phenylglycine because of some limitations in operation (i).

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Reference£º
Oxazolidine – Wikipedia,
Oxazolidine | C3H2509NO – PubChem