1707-77-3Relevant articles and documents
Efficient conversion of D-mannitol into 1,2:5,6-diacetonide with Aquivion-H as a recyclable catalyst
Bolchi, Cristiano,Appiani, Rebecca,Roda, Gabriella,Bertolini, Valentina,Arnoldi, Sebastiano,Pallavicini, Marco
, (2021)
Heterogeneous solid catalysis by the commercially available perfluorosulfonic ionomer Aquivion-H allowed 1,2:5,6-diacetonide of D-mannitol (1), immediate precursor of important unichiral C3-synthons, to be efficiently obtained from D-mannitol and 2,2-dimethoxypropane in DMF at room temperature. The 1,2-monoacetonide, whose intermediate formation is the rate-limiting step, could be almost completely converted into 1 with limited concurrent transformation of 1 into triacetonides. In line with recent literature reports, these results indicate that heterogeneous catalysis by Aquivion-H surpasses the performances of homogeneous acidic catalysis assuring, presumably for its peculiar morphology, a higher product selectivity. Easy recovery at the end of the reaction and recyclability are additional advantages of this solid acid catalyst.
PHEROMONES COLEOPTERA. COMMUNICATION 3. SYNTHESIS OF R-γ-HEXANOLIDE
Zhdankina, G. M.,Serebryakov, E. P.
, p. 2414 - 2415 (1985)
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Synthesis of d-mannitol substituted ether-linked bis-1,2,3-triazoles as models of gemini surfactants
Mohammed, Adnan Ibrahim,Abboud, Zaid Hassan,Alghanimi, Atheer Hamed Odda
, p. 5081 - 5083 (2012)
Readily available and low cost D-mannitol was converted into 1,2,5,6-di-O-isopropylidene-D-mannitol (1) in the presence of acetone and zinc chloride. Williamson etherfication of 1 with propargyl bromide afforded the bisalkyne 2 in a very good yield. 1,3-Dipolar cycloaddition of 2 with four different alkyl azides using click conditions gave four novel bistriazoles 3a-d. Removal of the acetal groups of 3a-d afforded the deprotected bistriazoles 4a-d in excellent yields. Products 3 and 4 represent models of gemini surfactants.
Synthesis and properties of bio-based polyurethanes bearing hydroxy groups derived from alditols
Hashimoto, Kazuhiko,Hashimoto, Naoya,Kamaya, Takehiko,Yoshioka, Junya,Okawa, Haruki
, p. 976 - 985 (2011)
Four kinds of bio-based polyurethanes bearing hydroxy groups in the pendants were synthesized by the polyaddition of D-mannitol- and D,L-erythritol-derived diols (1,2:5,6-di-O-isopropylidene-D-mannitol and 1,2-O-isopropylidene-D,L-erythritol) with hexamethylene diisocyanate and methyl (S)-2,6-diisocyanatohexanoate and the subsequent deprotection of the isopropylidene groups. They were hydrolyzed much more quickly than the corresponding protected polyurethanes at 50 °C and pH 7.0, although their hydrolytic degradation rate was lower than that of polyurethanes with saccharic and glucuronic lactone groups, which had been reported in our previous articles. The introduction of D-mannitol units to the polyether-polyurethanes containing poly(oxytetramethylene) glycol units also enhanced their hydrolyzibility.
Selective Preparation of Mono- and Diacetals of D-Mannitol
Debost, Jean-Louis,Gelas, Jacques,Horton, Derek
, p. 1381 - 1382 (1983)
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Novel cytotoxic amphiphilic nitro-compounds derived from a synthetic route for paraconic acids
Ribeiro, Talita A.,Machado-Ferreira, Erik,Guimar?es, Lohaine F.,Cavaleiro, Jéssica,Britto, Alan Messala A.,Redua, Nátaly,de Souza, Lucas Miguel Pereira,Pimentel, André S.,Picciani, Paulo H.S.,Oliveira, Osvaldo N.,Barreto, Cléber Bonfim,Soares, Carlos Augusto G.
, (2021/06/21)
A series of precursors for bioactive paraconic acids (PA) were synthesized and their cytotoxicity assessed on human cells in vitro. Two amphiphilic nitro-containing precursors, Nitro-C15-EED and the butanolide Nitro-C12-GBL, were cytotoxic at the micromolar scale, with higher activity on tumor HeLa cells than on HEK-293T of non-tumor origin. The structure of these molecules is simple but different from reported bioactive nitro compounds. Nitro-C12-GBL was generally more cytotoxic, but after short-term (2 h) exposure both compounds reached maximum cytotoxicity. At 72 h post-treatments of HeLa cells the final dose-response for Nitro-C12-GBL (LC50 = 21.9 μmol L?1) was close to that for Nitro-C15-EED (LC50 = 25.3 μmol L?1), corresponding to LC50s ~ 3–3.6 times lower than those on HEK-293T. Short-term treatments with 50 μmol L?1 of these compounds promoted comparable outcomes, reducing tumor cells viability up to 27–36% of the controls and preserving ~70% of HEK-293T viability at 72 h post-treatments. Reduced cytotoxicity was observed in cultures continuously exposed to the compounds for longer periods (24–72 h), especially on tumor cells, underlining short-term treatments as alternatives to antiproliferative strategies. Due to their amphiphilic nature, these compounds show spontaneous surface activity and adsorption onto Langmuir monolayers of dipalmitoyl phosphatidyl choline (DPPC), especially Nitro-C12-GBL. The effects on DPPC monolayers are indicative of a possible physiological action that depends on the interaction with the cell membranes. Coarse-grained molecular dynamics indicate that individualized molecules of Nitro-C15-EED and the less toxic PA precursors are susceptible to trapping into phospholipid films. In contrast, Nitro-C12-GBL consistently forms large aggregates with outward polar domains, which could favor interaction with phospholipid polar heads of biological membranes.
Design and preparation of a novel prolinamide-based organocatalyst for the solvent-free asymmetric aldol reaction
Martins, Rafaela de S.,Pereira, Mathias P.,de Castro, Pedro P.,Bombonato, Fernanda I.
, (2019/12/24)
The preparation of four novel organocatalysts as highly diastereo and enantioselective catalysts for the solvent-free asymmetric aldol reaction was described. These organocatalysts were synthesized in eight steps applying simple and commercially available starting materials. The best results were obtained for the proline-derived catalyst, providing access to the desired adducts in up to 95% yield, 1:19 syn/anti and 98% e.e. Moreover, even sterically bulky aldehydes and substituted cyclohexanones were well tolerated. DFT calculations and control experiments indicated that several hydrogen bonding interactions between the aldehyde and the enamine intermediate are responsible for the stereoselective chiral induction process and that the trifluoroacetate counter-anion is crucial for the attainment of higher stereoselectivities.
