Abstract:
Diastereomerically pure levoglucosenone alcohol, synthesized from levoglucosenone, upon hydrogenation on Raney Ni or Pd/BaSO4 undergoes epimerization at C2 atom caused by formation of cyrene by-product and its subsequent non-specific reduction. A microbiological stereospecific technique using baker's yeast (Saccharomyces cerevisiae) has been developed levoglucosenone for cyrene reduction into cyrene alcohol and also applied to reduce 4-alkoxy and 4-benzyloxy derivatives of cyrene.
Citation:
B. T. Sharipov, A. N. Davydova, L. Kh. Faizullina, F. A. Valeev, “Preparation of the diastereomerically pure 2S-hydroxy derivative of dihydrolevoglucosenone (cyrene)”, Mendeleev Commun., 29:2 (2019), 200–202
Linking options:
https://www.mathnet.ru/eng/mendc1471
https://www.mathnet.ru/eng/mendc/v29/i2/p200
This publication is cited in the following 12 articles:
Oscar Lamb, Johannes Puschnig, Stephen Glover, Ben W. Greatrex, “Acid‐Catalyzed Redox Isomerizations of 6,8‐Dioxabicyclo[3.2.1]octan‐4‐ols Provide Mechanistic Insights for Levoglucosenone Formation”, ChemSusChem, 2025
Caio M. Pacheco, Wesley Lima, Fernanda A. Lima, Mauro R. B. P. Gomez, Isabela G. da Silva, Leandro S. M. Miranda, Pierre M. Esteves, Ivaldo Itabaiana, Robert Wojcieszak, Raquel A. C. Leão, Rodrigo O. M. A. de Souza, “Levoglucosenone as a starting material for cascade continuous-flow synthesis of (R)-γ-carboxy-γ-butyrolactone”, RSC Adv., 14:47 (2024), 34611
Takumi Ichimura, Hiroki Maeda, Takuya Shimbayashi, Kohei Okubo, Masayuki Fukushima, Norimitsu Tohnai, Ken-ichi Fujita, Kouki Oka, “Sustainable hydrogen production & storage cycle with dihydrolevoglucosenone (Cyrene™): Hydrogen fixing and release based on alcoholic fermentation with Baker's yeast and dehydrogenation”, International Journal of Hydrogen Energy, 72 (2024), 815
Enzo Petracco, Amandine L. Flourat, Marie-Charlotte Belhomme, Stéphanie Castex, Fanny Brunissen, Fanny Brunois, Aurélien A. M. Peru, Florent Allais, Arnaud Haudrechy, “Green synthesis of (R)-3-hydroxy-decanoic acid and analogs from levoglucosenone: a novel access to the fatty acid moiety of rhamnolipids”, Front. Chem., 12 (2024)
Yadong Wang, Mingfei Dai, Gang Luo, Jiajun Fan, James H. Clark, Shicheng Zhang, “Preparation and Application of Green Sustainable Solvent Cyrene”, Chemistry, 5:4 (2023), 2322
Chuanqi Geng, Xinyu Li, Xiaojia Wu, Hui Yu, Fan Zhang, Zhiyong Zhou, Zhongqi Ren, “Liquid–liquid equilibrium and mechanism study on separation of short carbon chain hydrocarbon mixtures by Cyrene”, Can J Chem Eng, 101:8 (2023), 4731
L. Kh. Faizullina, Yu. S. Galimova, A. S Ryabova, N. F Galimzyanova, F. A Valeev, “Synthesis of 4-isopropyl derivatives of levoglucosenone”, Žurnal organičeskoj himii, 59:6 (2023), 797
Yu. A. Khalilova, L. Kh. Faizullina, Sh. M. Salikhov, F. A. Valeev, “Reactions of cyrene with formaldehyde”, Mendeleev Commun., 33:5 (2023), 648–649
Florian Diot-Néant, Louis M. M. Mouterde, Clémence Veith, Julien Couvreur, Stephen A. Miller, Florent Allais, “Sustainable One-Pot Synthesis and Polycondensation of a Levoglucosenone-Derived Cyclic Acetal Diol”, ACS Sustainable Chem. Eng., 10:31 (2022), 10132
L. Kh. Faizullina, Yu. S. Galimova, A. S. Ryabova, N. F. Galimzianova, F. A. Valeev, “Synthesis of 4-Isopropyl Derivatives of Levoglucosenone”, Russ J Org Chem, 58:12 (2022), 1797
L. Kh. Faizullina, Yu. S. Galimova, Yu. A. Khalilova, A. R. Tagirov, Sh. M. Salikhov, F. A. Valeev, “Regioselective reduction of keto groups in Michael adducts of levoglucosenone and cyclohexanone”, Mendeleev Commun., 32:5 (2022), 632–633
Rosario Figliolia, Paolo Cavigli, Clara Comuzzi, Alessandro Del Zotto, Denise Lovison, Paolo Strazzolini, Sabina Susmel, Daniele Zuccaccia, Maurizio Ballico, Walter Baratta, “CNN pincer ruthenium complexes for efficient transfer hydrogenation of biomass-derived carbonyl compounds”, Dalton Trans., 49:2 (2020), 453
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