50705-28-7Relevant academic research and scientific papers
Synthesis of a 3-Thiomannoside
Comba, María B.,Suárez, Alejandra G.,Sarotti, Ariel M.,Mangione, María I.,Spanevello, Rolando A.,Giordano, Enrique D. V.
, p. 1748 - 1751 (2016)
An efficient and straightforward synthesis of a novel 3-thiomannoside derivative (1,2,4,6-tetra-O-acetyl-3-S-acetyl-3-thio-β-d-mannopyranoside) was developed starting from levoglucosenone. A xanthate-thiocarbonate exchange under acidic conditions was the key step for the new C-S bond. The product was obtained enantiospecifically in very good overall yield.
Ring-Opening Metathesis Polymerization of Biomass-Derived Levoglucosenol
Debsharma, Tapas,Behrendt, Felix N.,Laschewsky, André,Schlaad, Helmut
, p. 6718 - 6721 (2019)
The readily available cellulose-derived bicyclic compound levoglucosenol was polymerized through ring-opening metathesis polymerization (ROMP) to yield polylevoglucosenol as a novel type of biomass-derived thermoplastic polyacetal, which, unlike polysaccharides, contains cyclic as well as linear segments in its main chain. High-molar-mass polyacetals with apparent weight-average molar masses of up to 100 kg mol?1 and dispersities of approximately 2 were produced despite the non-living/controlled character of the polymerization due to irreversible deactivation or termination of the catalyst/active chain ends. The resulting highly functionalized polyacetals are glassy in bulk with a glass transition temperature of around 100 °C. In analogy to polysaccharides, polylevoglucosenol degrades slowly in an acidic environment.
Synthesis of 2-amino derivatives of levoglucosenone
Valeev,Kalimullina,Salikhov,Shitikova,Tsypysheva,Safarov
, p. 521 - 525 (2004)
2-Amino derivatives of levoglucosenone were prepared by reaction of the 2-methanesulfonyl (or p-toluenesulfonyl) derivatives with ammonia, methylamine, or octylamine under various conditions. The analogous reaction did not occur for saturated derivative 15. The 2-amino-3,4-dihydro derivative was prepared by catalytic hydrogenation of unsaturated amine 9. 2004 Springer Science + Business Media, Inc.
Ring-Opening Metathesis Polymerization of Unsaturated Carbohydrate Derivatives: Levoglucosenyl Alkyl Ethers
Debsharma, Tapas,Schmidt, Bernd,Laschewsky, André,Schlaad, Helmut
, p. 2720 - 2728 (2021)
A series of biomass-derived levoglucosenyl alkyl ethers (alkyl = methyl, ethyl, n-propyl, isopropyl, and n-butyl) were synthesized and polymerized by ring-opening olefin metathesis polymerization using the Grubbs catalyst C793 at room temperature. Polymerizations were successfully performed in conventional solvents such as 1,4-dioxane and dichloromethane as well as in polar aprotic "green"solvents such as 2-methyltetrahydrofuran, dihydrolevoglucosenone (Cyrene), and ethyl acetate. The prepared polyacetals with degrees of polymerization of ～100 exhibit Schulz-Flory-type molar mass distributions and are thermoplastic materials with rather low glass transition temperatures in the range of 43-0 °C depending on the length of the alkyl substituent. Kinetic studies revealed that the polymerization proceeded rapidly to a steady state with a certain minimum monomer concentration threshold. When the steady state was reached, just about half of the [Ru] catalyst had been effective to initiate the polymerization, indicating that the initiation step was a slow process. The remaining catalyst was still active and did no longer react with monomers but with in-chain double bonds, cutting the formed polymer chains into shorter fragments. In the long term, all catalyst was consumed and propagating [Ru] chain ends were deactivated by the elimination of [Ru] from the chain ends to form inactive chains with terminal aldehyde groups.
Cellulose-Derived Functional Polyacetal by Cationic Ring-Opening Polymerization of Levoglucosenyl Methyl Ether
Debsharma, Tapas,Yagci, Yusuf,Schlaad, Helmut
, p. 18492 - 18495 (2019)
The unsaturated bicyclic acetal levoglucosenyl methyl ether was readily obtained from sustainable feedstock (cellulose) and polymerized by cationic ring-opening polymerization to produce a semicrystalline thermoplastic unsaturated polyacetal with relatively high apparent molar mass (up to ca. 36 kg mol?1) and decent dispersity (ca. 1.4). The double bonds along the chain can undergo hydrogenation and thiol–ene reactions as well as crosslinking, thus making this polyacetal potentially interesting as a reactive functional material.
Reactions of levoglucosenone and its derivatives with diazo compounds
Novikov,Rafikov,Shulishov,Konyushkin,Semenov,Tomilov, Yu. V.
, p. 327 - 334 (2009)
The reaction of levoglucosenone with methyl diazoacetate gives first 1-pyrazoline, which then, depending on the reaction conditions, either undergoes denitrogenation to form a mixture of cyclopropane and unsaturated compounds, or isomerizes into 2-pyrazoline capable of easy cyclodimerizing in the presence of pyridine through the addition of the N-H fragments to the carbonyl groups. The product of levoglucosenone reduction, 6,8-dioxabicyclo [3.2.1]oct-2-en-4-ol, affords the corresponding cyclopropane upon the action of diazomethane in the presence of a Pd catalyst, whereas its reaction with methyl diazoacetate in the presence of Rh2(OAc)4 leads to the insertion of methoxycarbonyl carbene into the OH bond. From the ester obtained, l-diazo-3-6,8-dioxabicyclo[3.2.1]oct-2-en-4-yloxypropan-2-one was synthesized in several steps, its denitrogenation under the action of copper compounds is accompanied by the intramolecular insertion of the carbene into the C(4)-H bond of the levoglucosenone fragment to yield the corresponding spirane.
Synthesis of tri-O-acetyl-D-allal from levoglucosenone
Giordano, Enrique D.V.,Frinchaboy, Agustina,Suárez, Alejandra G.,Spanevello, Rolando A.
, p. 4602 - 4605 (2012)
Tri-O-acetyl-d-allal has been enantiospecifically synthesized in six steps from levoglucosenone in 55% overall yield. A key step in the synthesis is the anhydro bridge ring-opening with concomitant formation of a 1,3-oxathiolane-2- thione ring.
SYNTHESIS OF 1,6:3,4-DIANHYDRO-β-D-TALOPYRANOSE FROM LEVOGLUCOSENONE: EPOXIDATION OF OLEFIN VIA trans-IODOACETOXYLATION
Matsumoto, Katsuya,Ebata, Takashi,Koseki, Koshi,Okano, Koji,Kawakami, Hiroshi,Matsushita, Hajime
, p. 1935 - 1947 (1992)
Levoglucosenone (1,6-anhydro-3,4-dideoxy-β-D-glycero-hex-3-enopyranos-2-ulose, 1) was converted to give 1,6:3,4-dianhydro-β-D-talopyranose (8) in good yield through stereoselective trans-iodoacetoxylation followed by basic hydrolysis.
Diastereoselective sulfa-Michael reactions controlled by a biomass-derived chiral auxiliary
Klepp, Julian,Podversnik, Harald,Puschnig, Johannes,Wallace, Andrew,Greatrex, Ben W.
supporting information, p. 3894 - 3903 (2019/06/18)
A family of chiral auxiliaries derived from the lignocellulosic biomass pyrolysis product levoglucosenone (LGO) has been screened in the sulfa-Michael reaction. When promoted by inorganic bases with potassium counterions, the auxiliary with geminal benzyl substituents showed diastereoselectivity up to 90:10 for a broad range of α,β-unsaturated esters.
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.
