Properties and Exciting Facts About (S)-tert-Butyl 4-(hydroxymethyl)-2,2-dimethyloxazolidine-3-carboxylate

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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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Reference:
Oxazolidine – Wikipedia,
Oxazolidine | C3H2322NO – PubChem

 

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Design, synthesis and in vitro evaluation on glucosamine-6P synthase of aromatic analogs of 2-aminohexitols-6P

The aminosugars are very important structural components of bacterial and fungi cell walls. Glucosamine-6-phosphate synthase (GlmS), which catalyses the first step of the aminosugar biosynthetic pathway i.e. the formation of D-glucosamine-6-phosphate from D-fructose-6- phosphate, is therefore an interesting target in the fight against microorganisms. In this work is described the synthesis of aromatic analogs of 2-amino-2-deoxy-D-glucitol-6- phosphate (ADGP) and its epimer 2-amino-2-deoxy-D-manitol-6-phosphate (ADMP), two important inhibitors of GlmS. The aromatic analogs displayed modest inhibitory activity against GlmS, with IC50 in the mmol L-1 range. 2010 Sociedade Brasileira de Quimica.

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Reference:
Oxazolidine – Wikipedia,
Oxazolidine | C3H2296NO – PubChem

 

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Grignard reactions to chiral oxazolidine aldehydes

Modest to high levels of asymmetric induction are observed with Grignard additions to Garner type aldehydes. The resultant secondary alcohols are important precursors of chiral building blocks for asymmetric synthesis and we have demonstrated that they can be readily converted into their respective gamma-hydroxy-beta-amino alcohols and beta-hydroxyamino acids. Additionally, aryloxy ethers, important components of many natural products, can be obtained from these precursors.

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Reference:
Oxazolidine – Wikipedia,
Oxazolidine | C3H2319NO – PubChem

 

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Photoredox-induced three-component Oxy-, Amino-, and Carbotrifluoromethylation of enecarbamates

A photoredox-catalzyed trifluoromethylation of enecarbamates process is reported. This pathway uses Togni’s reagent as the CF3 source and follows a radical/cationic pathway. Under the optimized conditions using [Ru(bpy)3(PF6)2] as the photocatalyst, a wide range of substituted enecarbamates can readily be difunctionalized by means of various O, N, and C nucleophiles.

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Reference:
Oxazolidine – Wikipedia,
Oxazolidine | C3H2291NO – PubChem

 

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Asymmetric allylboration of 2-N,3-O-isopropylidene-N-Boc-L-serinal: Diastereoselective synthesis of the calicheamicin gamma1(I) amino sugar

Syntheses of the calicheamicin amino sugar 6 and its erythro diastereomer 7 have been completed by a sequence involving the asymmetric allylboration of N-Boc-serinal acetonide L-8 with the tartrate ester modified allylboronates (R,R)-9 and (S,S)-9, respectively. The reaction of (R,R)-9 and L-8 in toluene provides 14 with 89:11 selectivity, whereas the reaction of (S,S)-9 with L-8 in Et2O provides the diastereomer 15 with 90:10 selectivity. It is shown that the relatively modest diastereoselectivity of these double asymmetric reactions is compromised by the low enantiomeric purity of 8 (86-87% ee), and data are provided indicating that these reactions should be highly diastereoselective (?95:5 in each case) if performed with enantiomerically pure aldehyde. The two diastereomeric homoallylic alcohols, 14 and 15, are easily elaborated into the targeted amino sugars 6 and 7 via the acetamide-substituted pyranosides 22 and 26. Methyl pyranosides 22a and 22e were shown to adopt preferentially the unexpected conformations B and D, with axial acetamide substituents, in nonpolar solvents, while the expected conformations A and C were strongly favored in d6-DMSO because of hydrogen bonding interactions with the solvent. The syntheses of 6 and 7 reported herein are expected to facilitate the design and synthesis of analogs of the calicheamicin aryl tetrasaccharide 3, which should prove useful in further analysis and applications of oligosaccharides as DNA binders.

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Reference£º
Oxazolidine – Wikipedia,
Oxazolidine | C3H2316NO – PubChem

 

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Orthogonally protected glycerols and 2-aminodiols: Useful building blocks in heterocyclic chemistry

The efficient synthesis of orthogonally protected glycerols, 2-aminopropane-1,3-diols and 2-aminobutane-1,4-diols that can constitute useful tools in heterocyclic chemistry, is reported. These interesting tri-functionalized small synthons were easily prepared from serine or aspartic acid. In addition, these substrates can be readily transformed into their iodide derivatives in very good yields. ARKAT USA, Inc.

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Reference£º
Oxazolidine – Wikipedia,
Oxazolidine | C3H2311NO – PubChem

 

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TREATMENT OF H. PYLORI INFECTIONS USING MTAN INHIBITORS

Methods of treating infections due to Helicobacter pylori (H. pylori), in particular in subjects having a peptic ulcer, are disclosed where the methods comprise administering inhibitors of H. pylori MTAN (5′-methylthioadenosine nucleosidase) to the subject.

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Reference£º
Oxazolidine – Wikipedia,
Oxazolidine | C3H2280NO – PubChem

 

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Design, Synthesis, and Evaluation of a Novel Series of Oxadiazine Gamma Secretase Modulators for Familial Alzheimer?s Disease

Herein we describe the design, synthesis, and evaluation of a novel series of oxadiazine-based gamma secretase modulators obtained via isosteric amide replacement and critical consideration of conformational restriction. Oxadiazine lead 47 possesses good in vitro potency with excellent predicted CNS drug-like properties and desirable ADME/PK profile. This lead compound demonstrated robust Abeta42 reductions and subsequent Abeta37 increases in both rodent brain and CSF at 30 mg/kg dosed orally.

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Oxazolidine – Wikipedia,
Oxazolidine | C3H2290NO – PubChem

 

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Metal-mediated alkynediol cycloisomerization: First and second generation formal total syntheses of didemniserinolipid B

A formal total synthesis of didemniserinolipid B was developed by employing a regioselective metal-mediated 6-endo-dig alkynol-cycloisomerization reaction. Two routes for the synthesis of key Burke’s intermediate have been developed. Our initial approach involved the introduction of a C17-alkynol followed by Pd-mediated cycloisomerization and then coupling with the serinol unit prior to the introduction of an alpha,beta-unsaturated ester unit through selective oxidation of 1-OH followed by a two-carbon Wittig homologation. Alternatively, the second generation strategy featuring the serinol coupling with the C17-alkynol followed by alkyne addition to the epoxide and subsequent Au-mediated cycloisomerization of an acetonide protected alkynediol unit has been executed. This approach has avoided several late stage protection-deprotection events.

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Reference£º
Oxazolidine – Wikipedia,
Oxazolidine | C3H2295NO – PubChem

 

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Design, synthesis and structure-activity relationship studies of a novel focused library of 2,3,4-substituted oxazolidines with antiproliferative activity against cancer cell lines

In the present work we describe the synthesis and antiproliferative evaluation of a focused library of 30 novel oxazolidines designed by modification of N-substituent, by ring variation, by alkyl variation or by extension of the structure. It was noted that carbamate and N,O-aminal groups were essential for activity. In general, replacement of the phenyl ring with pyridinyl was not tolerated. However, the introduction of a second phenyl ring with an appropriate spacer at the 3- or 4-position of the first phenyl ring generally enhanced the cytotoxic profile. Among all the prepared compounds, 24 was the most potent compound found in this class, being active on four of five cancer cell lines and it was 5-fold and 10-fold more potent than the lead compounds against HL60 and JURKAT cells, respectively. In addition, it showed relevant activity against MCF-7 and HCT-116 cells, which were resistant to lead. Moreover, 24 showed little antiproliferative activity against VERO, indicating low toxicity to normal cells. Thus, this compound has the potential to be developed as an anticancer agent.

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Reference£º
Oxazolidine – Wikipedia,
Oxazolidine | C3H2286NO – PubChem