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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Studies on a catalytic version of the Matteson asymmetric homologation reaction
Smith, Keith,Saleh, Basil A.,Alshammari, Mohammed B.,El-Hiti, Gamal A.,Elliott, Mark C.
supporting information, p. 4279 - 4284 (2021/05/31)
Studies of a catalytic asymmetric version of the Matteson reaction between dichloromethylboronates and organolithium reagents have been undertaken. From several different chiral catalytic systems studied, only one based on a mannitol derivative has given substantial asymmetric induction close to that previously achieved with a bis(oxazoline) derivative and ytterbium triflate. More detailed study of the latter reaction revealed that fresh ytterbium triflate actually reduced the level of asymmetric induction, while "aged"ytterbium triflate, or a fresh sample that had been treated with water, brought about improved induction. The implications of these findings are discussed.
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.
