53716-82-8Relevant articles and documents
Levoglucosenone-derived precursors for the stereoselective synthesis of methylene-expanded analogues of C-nucleosides
Brel, Valery K.,Samet, Aleksandr V.,Konyushkin, Leonid D.,Stash, Adam I.,Belsky, Vitaly K.,Semenov, Victor V.
, p. 44 - 46 (2015)
Simple chiral precursors for the preparation of methylene-expanded C-nucleosides were developed, using as key steps pyrolysis of cellulose to levoglucosenone followed by hydrogenation and introduction of vinyl and ethynyl fragments to the 2-position.
Determination of the Relative Configuration of Terminal and Spiroepoxides by Computational Methods. Advantages of the Inclusion of Unscaled Data
Zanardi, María M.,Suárez, Alejandra G.,Sarotti, Ariel M.
, p. 1873 - 1879 (2017)
The assignment of the relative configuration of spiroepoxides or related quaternary carbon-containing oxiranes can be troublesome and difficult to achieve. The use of GIAO NMR shift calculations can provide helpful assistance in challenging cases of structural elucidation. In this regard, the DP4 probability is one of the most popular methods to be employed when only one set of experimental data is available, though modest results were obtained when dealing with spiroepoxides. Recently, we introduced an improved probability (DP4+) that includes the use of both scaled and unscaled NMR data computed at higher levels of theory. Here, we report a comprehensive study to explore the scope and limitations of the DP4+ methodology in the stereoassignment of terminal or spiroepoxides bearing a wide variety of molecular complexity and conformational freedom. The excellent levels of correct classification achieved were interpreted on the basis of a constructive compensation of errors upon using both scaled and unscaled proton and carbon data. The advantages of the DP4+ methodology in solving two case studies that could not be unequivocally assigned by NOE experiments are also provided.
Enzymatic reduction of levoglucosenone by an alkene reductase (OYE 2.6): A sustainable metal- and dihydrogen-free access to the bio-based solvent Cyrene
Mouterde, Louis M. M.,Allais, Florent,Stewart, Jon D.
, p. 5528 - 5532 (2018)
Levoglucosenone (LGO) has been successfully converted into the green polar aprotic solvent 2H-LGO (aka Cyrene) through an enzymatic process involving alkene reductases: wild-type Old Yellow Enzyme 2.6 (OYE 2.6 wt.) from Pichia stipitis and its mutant (OYE 2.6 Tyr78Trp) present the best conversion rates. This enzymatic process has been optimized in order to avoid the formation of the side-product (1R,2S)-2-hydroxy-6,8-dioxabicyclo[3.2.1]octan-4-one (OH-LGO) and reach total conversion (99%). Cyrene was then successfully isolated by continuous extraction in quantitative yield (99%).
The Co-Entrapment of a homogeneous catalyst and an ionic liquid by a sol-gel method: Recyclable Ionogel hydrogenation catalysts
Craythorne, Steven J.,Lorenzini, Kris Anderson Fabio,McCausland, Christina,Smith, Emily F.,Licence, Peter,Marr, Andrew C.,Marr, Patricia C.
, p. 7094 - 7100 (2009)
Molecular hydrogenation catalysts have been co-entrapped with the ionic liquid [Bmim]NTf2 inside a silica matrix by a sol-gel method. These catalytic ionogels have been compared to simple catalyst-doped glasses, the parent homogeneous catalysts, commercial heterogeneous cata-lysts, and Rh-doped mesoporous silica. The most active ionogel has been characterised by transmission electron mi-croscopy, X-ray photoelectron spectroscopy, and solid state NMR before and after catalysis. The ionogel catalysts were found to be remarkably active, recyclable and resistant to chemical change. 2009 Wiley-VCH Verlag GmbH & Cu. KGaA.
Stereochemical aspects of the Beckman rearrangement of oximes of levoglucosenone and its dihydro derivative. Enantioselective synthesis of (+)-γ-pelargonolactone
Valeev,Gorobets,Tsypysheva,Singizova,Kalimullina,Safarov,Shitikova,Miftakhov
, p. 563 - 568 (2003)
Regiospecific C5-halogenation with retention of configuration occurred upon Beckman fragmentation of levoglucosenone oxime using SOCl 2 or PBr3. On the other hand, the oxime of its dihydro derivative gave under these conditions the C6-substitution product. A stereoselective synthetic scheme for (+)-γ-pelargonolactone, an attractant for the rice and corn weevils Sitophiltus zeamais, was developed from the fragmentation product of levoglucosenone oxime.
Reactivity, Selectivity, and Synthesis of 4-C-Silylated Glycosyl Donors and 4-Deoxy Analogues
J?ger Pedersen, Martin,Pedersen, Christian Marcus
supporting information, p. 2689 - 2693 (2020/12/01)
A method for introducing dimethylphenylsilyl at the 4-position in carbohydrates has been developed. Two C-silylated glycosyl donors were prepared via levoglucosenone, starting from cellulose. The glycosylation properties were studied using three glucoside
METHOD FOR CONVERTING LEVOGLUCOSENONE INTO 4-HYDROXYMETHYL BUTYROLACTONE AND 4-HYDROXYMETHYL BUTENOLIDE WITHOUT USING ANY ORGANIC SOLVENT AND CATALYST
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Paragraph 0063-0065, (2019/07/23)
The invention relates to a method for converting levoglucosenone into 4-hydroxymethyl butyrolactone and 4-hydroxymethyl butenolide without using any solvent or catalyst, wherein the oxidation and hydrolysis of the levoglucosenone or hydrogenated levoglucosenone are carried out in a single step using an aqueous solution of H2O2.
Tuning zirconia-supported metal catalysts for selective one-step hydrogenation of levoglucosenone
Mazarío, Jaime,Parre?o Romero, Miriam,Concepción, Patricia,Chávez-Sifontes, Marvin,Spanevello, Rolando A.,Comba, María B.,Suárez, Alejandra G.,Domine, Marcelo E.
, p. 4769 - 4785 (2019/09/09)
Levoglucosenone, directly produced from cellulose-containing residual biomass via pyrolysis treatments, is believed to be a promising bio-renewable platform for both fine and commodity chemicals. In this work, the possibilities given by tuneable catalysts based on Pd and Pt supported on metallic oxides to produce the desired product in the one-pot hydrogenation of levoglucosenone are evaluated. Particularly, the excellent catalytic performance of Pd/ZrO2 and Pt/ZrO2 type materials for the synthesis of dihydrolevoglucosenone (or Cyrene) and levoglucosanol, respectively, during the mild hydrogenation of levoglucosenone is demonstrated. In the Cyrene synthesis, the Pd/t-ZrO2 material showed the best catalytic activity compared to other Pd-supported on metallic oxides. This catalyst achieved nearly 95% yields of Cyrene by working under mild reaction conditions, with very low catalyst loadings (≈3 wt%) and using water as the solvent. On the other hand, the one-pot hydrogenation of levoglucosenone to levoglucosanol is reported for the first time with a Pt-based heterogeneous catalyst (Pt/ZrO2-mix, yield ≈90%), by working at low temperatures and mild H2 pressures with water as the solvent. Comparison of the results attained with other Pt-supported metallic oxides let us to conclude that the metal crystal facets (specifically the 100 facet) play an important role in the hydrogenation process to give levoglucosanol selectively. In addition, the stability and re-usability of both catalysts under operational conditions are also evaluated. Finally, catalytic tests including the use of crude bio-liquids obtained from cellulose-rich biomass pyrolysis and containing ≈66 wt% of levoglucosenone are also assayed, thus demonstrating the possibility of scaling-up the process over these metals supported on zirconia catalysts.
Preparation of the diastereomerically pure 2S-hydroxy derivative of dihydrolevoglucosenone (cyrene)
Sharipov, Bulat T.,Davydova, Anna N.,Faizullina, Liliya Kh.,Valeev, Farid A.
, p. 200 - 202 (2019/04/25)
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
Synthesis and fungicidal activity of methylsulfanylmethyl ether derivatives of levoglucosenone
Sharipov, Bulat T.,Davidova, Anna N.,Ryabova, Alena S.,Galimzyanova, Nailya F.,Valeev, Farid A.
, p. 31 - 37 (2019/02/25)
[Figure not available: see fulltext.] A series of derivatives were synthesized on the basis of levoglucosenone that contained hydroxy groups at the С-4 atom or С-2 and С-4 atoms or a hydroxy and methyl group at the С-4 atom. In addition, 4-hydroxymethylbutanolides were synthesized. Derivatives containing hydroxy groups were obtained as methylsulfanylmethyl ethers. It was established that compounds containing a 6,8-dioxabicyclo[3.2.1]-octane ring exhibited fungicidal activity against Rhizoctonia solani. It was shown that the presence of a methylsulfanylmethyl moiety in the ring could increase the fungicidal activity of compounds.
