- Silicate complexes of sugars in aqueous solution
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Certain sugars react readily with basic silicic acid to form soluble 2/1 (sugar/silicic acid) silicate complexes. Failure of monohydroxy compounds to give soluble products under these conditions indicates that the sugar silicates are chelates: five-membered diolato rings. Only furanose forms react. Pyranose sugars are stable under these conditions. Because all glycosides fail to react with silicic acid under these conditions, reaction appears to involve the anomeric position (C1 in aldoses, C2 in ketoses), which has a more acidic hydroxy group. Reaction is completed only when the anomeric hydroxy group is cis to an adjacent hydroxy group. The appropriate furanose form must have sufficient natural abundance and solubility to provide an observable product, as measured by 29Si and 13C NMR spectroscopy. These structural and practical constraints rationalize the successful reaction of the monosaccharides ribose, xylose, lyxose, talose, psicose, fructose, sorbose, and tagatose and the disaccharides lactulose, maltulose, and palatinose. Glucose, mannose, galactose, and sucrose, among others, failed to form complexes. This high selectivity for formation of sugar silicates may have ramifications in prebiotic chemistry.
- Lambert, Joseph B.,Lu, Gang,Singer, Stephanie R.,Kolb, Vera M.
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Read Online
- Dehydration of erythritol in high-temperature carbonated water
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Intramolecular dehydration of erythritol to 1,4-anhydroerythritol proceeded in liquid water at 573 K. The initial formation rate and final yield of 1,4-anhydroerythritol were 0.50 mmol h?1 and 71%, respectively. Addition of carbon dioxide up to the pressure of 17.7 and 24.8 MPa to water solvent at 573 K, the initial product formation rates dramatically increased to 1.45 and 2.10 mmol h?1, respectively; however, the final yields were almost the same as 73 and 71%, respectively. These results showed that the protons derived from carbonic acid catalyzed the intramolecular dehydration and the concentration of proton increased with an increase in the carbon dioxide pressure introduced.
- Taniguchi, Kenkichi,Nanao, Hidetaka,Sato,Yamaguchi, Aritomo,Shirai, Masayuki
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- A practical and scaleable preparation of 1,4-anhydroerythritol
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A practical and efficient kilogram-scale preparation of 1,4-anhydroerythritol from meso-erythritol is described. A novel silica gel and sodium bicarbonate slurry/filtration protocol is utilized to purify the product, giving commercial-grade material in 60-65% yield.
- Childers, Karla G.,Dreher, Spencer D.,Lee, Jaemoon,Williams, J. Michael
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Read Online
- Hydrido-bis(meso-oxolanylen-3,4-dioxy)-λ5-phosphane
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The symmetric hydrido-spiro-λ5-phosphane derived from anhydroerythritol (meso-oxolane-3,4-diol, AnEryt), HP(AnErytH- 2)2(3), was prepared by two different synthetic protocols. One route involves a three step synthesis starting from phosphorus trichloride via 2-chloro-tetrahydro-furo[3,4- d][1,3,2]dioxaphosphole (1) and diethyl-(tetrahydro-furo[3,4-d][1,3,2] dioxaphosphol-2-yl)-amine (2) as intermediates. The first intermediate, P(AnErytH- 2)Cl (1), was isolated as a crystalline solid and its structure was determined by single crystal X-ray diffraction. 1 is the first example of a halogeno substituted phosphane derived from an aliphatic diol whose molecular structure in the solid state was determined by X-ray diffraction studies. Alternatively, the title compound can also be obtained in a one-pot procedure starting from tris(N,N-dimethylamino)phosphane. All new compounds were characterized by their physical constants (melting point, refractory index), NMR, IR, Raman, UV/VIS, mass spectrometry, as well as elemental analysis. Some spectroscopic proofs for the spiro nature of the title compound are given. Copyright Taylor & Francis Group, LLC.
- Betz, Richard,Kluefers, Peter
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Read Online
- METHOD FOR THE HYDRODEOXYGENATION OF OXYGENATED COMPOUNDS TO UNSATURATED PRODUCTS
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The invention relates to methods of hydrodeoxygenation of oxygenated compounds into compounds with unsaturated carbon-carbon bonds, comprising the steps of: a) providing a reaction mixture comprising, an oxygenated compound containing one or more of a hydroxyl, keto or aldehyde group, an ionic liquid, a homogeneous metal catalyst, and carbon monoxide or a carbon monoxide releasing compound, b) reacting said reaction mixture under a H2 atmosphere at acidic conditions at a temperature between 180 and 250 °C and a pressure between 10 and 200 bar.
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Page/Page column 11
(2021/01/23)
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- Efficient synthesis of α-branched purine-based acyclic nucleosides: Scopes and limitations of the method
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An efficient route to acylated acyclic nucleosides containing a branched hemiaminal ether moiety is reported via three-component alkylation of N-heterocycle (purine nucleobase) with acetal (cyclic or acyclic, variously branched) and anhydride (preferentially acetic anhydride). The procedure employs cheap and easily available acetals, acetic anhydride, and trimethylsilyl trifluoromethanesulfonate (TMSOTf). The multi-component reaction is carried out in acetonitrile at room temperature for 15 min and provides moderate to high yields (up to 88%) of diverse acyclonucleosides branched at the aliphatic side chain. The procedure exhibits a broad substrate scope of N-heterocycles and acetals, and, in the case of purine derivatives, also excellent regioselectivity, giving almost exclusively N-9 isomers.
- Dra?ínsky, Martin,Frydrych, Jan,Janeba, Zlatko,Slavětínská, Lenka Po?tová
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- METHODS AND COMPOSITIONS FOR BIORENEWABLE POLYESTERS DERIVED FROM CAMPHORIC ACID
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In one aspect, the disclosure relates to biorenewable polyesters and polyester copolymers derived from camphoric acid, methods of making same, and articles comprising same. The disclosed biorenewable polyesters can have a Mn of from about 5,000 Da to about 500,000 Da. Also disclosed herein is the preparation of various monomers useful in the reactions disclosed herein, e.g., cis-1,4-anhydroerythritol and bis(2-hydroxyethyl) camphorate. In various aspects, the disclosed biorenewable polyesters and polyester copolymers can be used to the production of various articles utilizing a conventional polyester or polyester copolymer, that is, to replace, in part or in whole, a conventional nonbiorenewable polyester or polyester copolymer. This abstract is intended as a scanning tool for purposes of searching in the particular art and is not intended to be limiting of the present disclosure.
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Paragraph 0180
(2020/08/28)
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- A versatile biobased continuous flow strategy for the production of 3-butene-1,2-diol and vinyl ethylene carbonate from erythritol
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A versatile, tunable and robust continuous flow procedure for the deoxydehydration (DODH) of biobased erythritol toward 3-butene-1,2-diol is described. The procedure relies on specific assets of multistep continuous flow processing. Detailed mechanistic and computational studies on erythritol show that either 3-butene-1,2-diol or butadiene are obtained in high selectivity and yield on demand, as a function of the DODH reagent/substrate ratio and of the process parameters. Short reaction times (1-15 min) at high temperature (225-275 °C) and moderate pressure are reported. 3-Butene-1,2-diol is then further converted downstream into its corresponding carbonate, i.e. 4-vinyl-1,3-dioxolan-2-one (vinyl ethylene carbonate), an important industrial building block. The carbonation step uses a supported organocatalyst, and could be directly concatenated to the first DODH step. This unprecedented procedure also relies on a unique combination of on- and off-line analytical protocols for reaction monitoring and product quantification, and offers a biobased strategy toward important industrial building blocks otherwise petrosourced.
- Tshibalonza, Nelly Ntumba,Gérardy, Romaric,Alsafra, Zouheir,Eppe, Gauthier,Monbaliu, Jean-Christophe M.
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supporting information
p. 5147 - 5157
(2018/11/26)
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- A strategy of ketalization for the catalytic selective dehydration of biomass-based polyols over H-beta zeolite
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Biomass contains plentiful hydroxyl groups that lead to an oxygen-rich structure compared to petroleum-based chemicals. Dehydration is the most energy-efficient technique to remove oxygen; however, multiple similar vicinal hydroxyl groups in sugar alcohols impose significant challenges for their selective dehydration. Here, we present a novel strategy to control the etherification site in sugar alcohols by the ketalization of the vicinal-diol group for the highly selective formation of tetrahydrofuran derivatives. A ketone firstly reacts with terminal vicinal hydroxyl groups to form the 1,3-dioxolane structure. This structure of the constrained 1,3-dioxolane ring would improve the accessibility of reactive groups to facilitate intramolecular etherification. As a better leaving group than water, the ketone can also promote intramolecular etherification. Consequently, a range of tetrahydrofuran derivatives are produced in excellent yields with the H-beta zeolite catalyst under mild reaction conditions. This strategy opens up new opportunities for the efficient upgrading of biomass via the modification or protection of hydroxyl groups.
- Che, Penghua,Lu, Fang,Si, Xiaoqin,Ma, Hong,Nie, Xin,Xu, Jie
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supporting information
p. 634 - 640
(2018/02/14)
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- Selective C?O Hydrogenolysis of Erythritol over Supported Rh-ReOx Catalysts in the Aqueous Phase
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Bimetallic Rh-ReOx (Re/Rh molar ratio 0.4–0.5) catalysts supported on TiO2 and ZrO2 were prepared by the successive impregnation of dried and calcined unreduced supported Rh catalysts. Their catalytic performances were evaluated in the hydrogenolysis of erythritol to butanetriols (BTO) and butanediols (BDO) in aqueous solution at 150–240 °C under 30–120 bar H2. The activity depended on the nature of the support, and the highest selectivity to BTO and BDO at 80 % conversion was 37 and 29 %, respectively, in the presence of 3.7 wt %Rh-3.5 wt %ReOx/ZrO2 at 200 °C under 120 bar. The characterization of the catalysts by CO chemisorption, TEM with energy-dispersive X-ray spectroscopy, thermogravimetric analysis with MS, and X-ray photoelectron spectroscopy suggests a different distribution and reducibility of Re species over the supported Rh nanoparticles, which depends on the support.
- Said, Achraf,Da Silva Perez, Denilson,Perret, Noémie,Pinel, Catherine,Besson, Michèle
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p. 2768 - 2783
(2017/07/28)
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- MANUFACTURING METHOD OF ANHYDROSUGAR ALCOHOL
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PROBLEM TO BE SOLVED: To provide a technology for enhancing yield of anhydrosugar alcohol, a conducting form of a continuous reactions and effective manufacturing method of anhydrosugar alcohol. SOLUTION: By using a specific organic solvent as a solvent and conducting a dehydration reaction of sugar alcohol in presence of the organic solvent and a catalyst, a separation of the catalyst and a product after completion of the reaction becomes easy and anhydrosugar alcohol can be manufactured at high yield and high selectivity. The anhydrosugar alcohol can be manufactured at high yield and high selectivity by extracting the anhydrosugar alcohol by using the organic solvent from the product obtained by a reaction for dehydrating sugar alcohol. SELECTED DRAWING: None COPYRIGHT: (C)2017,JPOandINPIT
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Paragraph 0046; 0065; 0070
(2017/12/01)
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- Intramolecular dehydration of biomass-derived sugar alcohols in high-temperature water
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The intramolecular dehydration of biomass-derived sugar alcohols d-sorbitol, d-mannitol, galactitol, xylitol, ribitol, l-arabitol, erythritol, l-threitol, and dl-threitol was investigated in high-temperature water at 523-573 K without the addition of any acid catalysts. d-Sorbitol and d-mannitol were dehydrated into isosorbide and isomannide, respectively, as dianhydrohexitol products. Galactitol was dehydrated into anhydrogalactitols; however, the anhydrogalactitols could not be dehydrated into dianhydrogalactitol products because of the orientation of the hydroxyl groups at the C-3 and C-6 positions. Pentitols such as xylitol, ribitol, and l-arabitol were dehydrated into anhydropentitols. The dehydration rates of the pentitols containing hydroxyl groups in the trans form, which remained as hydroxyl groups in the product tetrahydrofuran, were larger than those containing hydroxyl groups in the cis form because of the structural hindrance caused by the hydroxyl groups in the cis form during the dehydration process. In the case of the tetritols, the dehydration of erythritol was slower than that of threitol, which could also be explained by the structural hindrance of the hydroxyl groups. The dehydration of l-threitol was faster than that of dl-threitol, which implies that molecular clusters were formed by hydrogen bonding between the sugar alcohols in water, which could be an important factor that affects the dehydration process.
- Yamaguchi, Aritomo,Muramatsu, Natsumi,Mimura, Naoki,Shirai, Masayuki,Sato, Osamu
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p. 2714 - 2722
(2017/08/17)
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- Kinetic analysis of aqueous-phase cyclodehydration of 1,4-butanediol and erythritol over a layered niobium molybdate solid acid
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Aqueous-phase reactions are desirable for the transformation of biomass-derived species because the use of water is inherently environmentally friendly. Cyclodehydration of C4 diols in aqueous solution was examined using a variety of water-tolerant solid acids including H-type zeolites (H-ZSM5, H-mordenite, H-beta), Amberlyst-15 ion-exchange resin, niobic acid and layered HNbMoO6. Cyclodehydration of 1,4-butanediol (HO-CH2CH2CH2CH2-OH) and erythritol (HO-CH2CH-OHCH-OHCH2-OH) proceeded on three of the Br?nsted solid acids, HNbMoO6, H-ZSM5 and Amberlyst-15. Although HNbMoO6 showed moderate activity for 1,4-butanediol dehydration, it exhibited the highest activity for erythritol dehydration. Kinetic analysis indicated that 1,4-butanediol and erythritol dehydration over HNbMoO6 followed a Tamaru-type mechanism with two successive irreversible steps. A statistical mechanics analysis of the pre-exponential factor gave good agreement with experimental results, in which the pre-exponential factor for erythritol dehydration was much larger than that for 1,4-butanediol dehydration. Both erythritol and 1,4-butanediol could be intercalated in the interlayer spaces of the oxide. The expansion of the interlayer spaces for erythritol was, however, much larger than that for 1,4-butanediol. This improvement of accessibility is considered to be responsible for the higher reactivity of erythritol.
- Takagaki, Atsushi
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p. 791 - 799
(2016/02/18)
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- Lewis acid promoted ruthenium(II)-catalyzed etherifications by selective hydrogenation of carboxylic acids/esters
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Ethers are of fundamental importance in organic chemistry and they are an integral part of valuable flavors, fragrances, and numerous bioactive compounds. In general, the reduction of esters constitutes the most straightforward preparation of ethers. Unfortunately, this transformation requires large amounts of metal hydrides. Presented herein is a bifunctional catalyst system, consisting of Ru/phosphine complex and aluminum triflate, which allows selective synthesis of ethers by hydrogenation of esters or carboxylic acids. Different lactones were reduced in good yields to the desired products. Even challenging aromatic and aliphatic esters were reduced to the desired products. Notably, the in situ formed catalyst can be reused several times without any significant loss of activity. An assist from Al: A bifunctional catalyst system consisting of a Ru/phosphine complex and aluminum triflate allows selective hydrogenation of esters to ethers. A variety of lactones were reduced to the desired products in good yields. The catalyst further provides a general method for the reduction of linear esters and reductive etherification of carboxylic acids with alcohols.
- Li, Yuehui,Topf, Christoph,Cui, Xinjiang,Junge, Kathrin,Beller, Matthias
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supporting information
p. 5196 - 5200
(2015/04/27)
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- METHOD FOR PRODUCING 3-HYDROXYTETRAHYDROFURAN AND METHOD FOR PRODUCING 1, 3-BUTANE DIOL
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An object of the present invention is to provide a method for producing 3-hydroxytetrahydrofuran that can be used as a raw material for 1,3-butane diol, using as a raw material a compound that can be derived from biomass. The present invention relates to a method for producing 3-hydroxytetrahydrofuran including a step of reacting 1,4-anhydroerythritol and hydrogen to produce 3-hydroxytetrahydrofuran. In the production method, the step of reacting 1,4-anhydroerythritol and hydrogen is preferably allowed to proceed in the presence of a catalyst comprising a carrier and at least one oxide selected from the group consisting of an oxide of a Group 6 element and an oxide of a Group 7 element, the oxide being supported on the carrier.
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- Carbon Dioxide as a Protecting Group: Highly Efficient and Selective Catalytic Access to Cyclic cis-Diol Scaffolds
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The efficient and highly selective formation of a wide range of (hetero)cyclic cis-diol scaffolds using aminotriphenolate-based metal catalysts is reported. The key intermediates are cyclic carbonates, which are obtained in high yield and with high levels of diastereo- and chemoselectivity from the parent oxirane precursors and carbon dioxide. Deprotection of the carbonate structures affords synthetically useful cis-diol scaffolds with different ring sizes that incorporate various functional groups. This atom-efficient method allows the simple construction of diol synthons using inexpensive and accessible precursors and green metal catalysts and showcases the use of CO2 as a temporary protecting group. Protective Carbon: Aminotriphenolate complexes of FeIII and AlIII are highly efficient and selective catalysts for the conversion of functional (multi)cyclic oxiranes into the corresponding cis carbonates. Basic hydrolysis of the latter provides a series of useful cyclic cis-diol scaffolds in high yield. In this process, CO2 acts as both a temporary protecting group and an oxygen donor.
- Laserna, Victor,Fiorani, Giulia,Whiteoak, Christopher J.,Martin, Eddy,Escudero-Adán, Eduardo,Kleij, Arjan W.
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supporting information
p. 10416 - 10419
(2016/02/18)
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- Transfer hydrogenation as a redox process in nucleotides
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Using a combined theoretical and experimental strategy, the heats of hydrogenation of the nucleotide bases uracil, thymine, cytosine, adenine, and guanine have been determined. The most easily hydrogenated base is uracil, followed by thymine and cytosine. Comparison of these hydrogenation enthalpies with those of ketones and aldehydes derived from sugar models indicates the possibility of near-thermoneutral hydrogen transfer between uracil and the sugar phosphate backbone in oligonucleotides. (Figure Presented)
- Achrainer, Florian,Emel'yanenko, Vladimir N.,Tantawy, Waled,Verevkin, Sergey P.,Zipse, Hendrik
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p. 10426 - 10429
(2015/04/14)
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- Ring expansion of cyclic 1,2-diols to form medium sized rings via ruthenium catalyzed transfer hydrogenative [4+2] cycloaddition
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A new method for the ring expansion of cyclic diols is described. Using improved conditions for the ruthenium(0) catalyzed cycloaddition of cyclic 1,2-diols with 1,3-dienes, fused [n.4.0] bicycles 3a-3r (n = 3-6) are formed, which upon exposure to iodosobenzene diacetate engage in oxidative cleavage to form the 9-12 membered rings 4a-4r. the Partner Organisations 2014.
- Kasun, Zachary A.,Geary, Laina M.,Krische, Michael J.
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supporting information
p. 7545 - 7547
(2014/07/07)
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- Intramolecular etherification of five-membered cyclic carbonates bearing hydroxyalkyl groups
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We report a new one-pot synthetic route to tetrahydrofuran derivatives, which were unexpectedly produced under basic conditions by intramolecular etherification of substituted five-membered cyclic carbonates. For alcohols with vicinal hydroxyl groups, and additional OH groups at the β-position, intramolecular etherification leading to 3-hydroxytetrahydrofuran derivatives was observed. These reactions were studied for compounds having from 2 to 6 hydroxyl groups per molecule, and the mechanism was proposed. The developed method provides a new environmentally friendly approach to the synthesis of five-membered cyclic ether derivatives under non-acidic conditions. The Royal Society of Chemistry.
- Tomczyk, Karolina M.,Gunka, Piotr A.,Parzuchowski, Pawel G.,Zachara, Janusz,Rokicki, Gabriel
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p. 1749 - 1758
(2013/02/22)
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- Polymer-mediated cyclodehydration of alditols and ketohexoses
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The polymer PEDOT+ (1 or 2) mediates a cyclodehydration reaction with alditols 3, 5, 7, 9, in hydrocarbon solvents, to give cyclic ethers 4, 6, 8, or 10, respectively, in high yield with a trivial isolation protocol. Polymers 1 or 2 also mediate the cyclodehydration of ketohexoses such as D-fructose, but not aldohexoses, to the important industrial intermediate 5-hydroxymethylfurfural (17), under milder conditions when compared to reactions mediated by mineral acids. A cascade reaction with ketohexoses is observed in toluene via cyclodehydration followed by Friedel-Crafts alkylation of the initially formed benzylic alcohol to give 16.
- Onorato, Amber,Pavlik, Christopher,Invernale, Michael A.,Berghorn, Ian D.,Sotzing, Gregory A.,Morton, Martha D.,Smith, Michael B.
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experimental part
p. 1662 - 1670
(2011/12/02)
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- An efficient didehydroxylation method for the biomass-derived polyols glycerol and erythritol. Mechanistic studies of a formic acid-mediated deoxygenation
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An efficient 1,2-deoxygenation method, involving an unexpected mechanism, was found for simple diols and for biomass-derived polyols (glycerol and erythritol) that results in the conversion of the 1,2-dihydroxy group to a carbon-carbon double bond.
- Arceo, Elena,Marsden, Peter,Bergman, Robert G.,Ellman, Jonathan A.
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supporting information; experimental part
p. 3357 - 3359
(2009/12/26)
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- An unexpectedly facile cyclization of polyhydric alcohols
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Image Presented Contrary to previous reports in the literature, the reaction of polyhydric alcohols such as sorbitol or mannitol gives good yields of the tetrahydroxyoxepane derivative in the presence of an acid catalyst, in refluxing toluene, with complete retention of stereochemistry.
- Pavlik, Christopher,Onorato, Amber,Castro, Steve,Morton, Martha,Peczuh, Mark,Smith, Michael B.
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supporting information; experimental part
p. 3722 - 3725
(2011/02/28)
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- The solvent-free thermal dehydration of tetritols on zeolites
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A new alditol dehydration method at high temperatures, in the presence of molecular sieves without solvent in an argon atmosphere, is described. Investigations on tetritols have been carried out. Products arising after the intramolecular and intermolecular elimination of water, with retention or inversion of the configuration of asymmetric carbon atoms, were observed. Complete analytical separation of reaction products was achieved by means of GLC. The chemical structures of the compounds obtained were assigned using co-injection with standards, GLC-CIMS and GLC-EIMS analyses. Two intermolecular dehydration products of tetritols were isolated by HPLC and identified by 1H and 13C NMR spectroscopy. Copyright (C) 2000 Elsevier Science Ltd.
- Kurszewska, Maria,Skorupa, Eugenia,Kasprzykowska, Regina,Sowinski, Pawel,Wisniewski, Andrzej
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p. 241 - 249
(2007/10/03)
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- A simple conversion of polyols into anhydroalditols
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A simple procedure, which consists of direct heating of pyridinium chloride and the starting material, is described for the dehydration of alditols. Anhydroalditols, of great interest for various applications, are thus obtained, and the selectivity of the reaction is discussed. Some selective protections for further uses of these products are studied.
- Duclos,Fayet,Gelas
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p. 1087 - 1090
(2007/10/02)
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- Enantiomerically Pure (R)- and (S)-3-Benzyloxy-2,3-dihydrofuran: Versatile Precursors for the Synthesis of Protected Glycerinaldehydes
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Pure enantiomers of 3-benzyloxy-2,3-dihydrofuran were prepared and converted into 2-O-benzyl-3-O-formyl-glycerinaldehyde.
- Altenbach, Hans-Josef,Wolf, Eckardt
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p. 2155 - 2158
(2007/10/02)
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- Tetrahydrofuran derivatives and process for their production
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A tetrahydrofuran derivative of the formula: STR1 wherein each of R1 and R2 is an alkyl group having from 1 to 20 carbon atoms, and the two alkoxy groups OR1 and OR2 take a cis form to the plane of the tetrahydrofuran ring.
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- Nonlinear Regression Models of Multicomponent Interactions of Anhydropolyols with Aqueous Ammonium Ion by Carbon-13 Nuclear Magnetic Resonance
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The anhydropolyhydric alcohols 1,4-anhydroerythritol and 1,4- anhydrothreitol were synthesized from the corresponding tetratols via acid-catalyzed dehydration, under vacuum, using H+ ion exchange resin.Comparison of temperature-dependent 13C NMR chemical shifts i aqueous and nonaqueous solvents demonstrated a significant molecular association interaction between 1,4-anhydroerythritol and water.The chemical shifts of C(1) and C(2) of 1,4-anhydrothreitol and C(1) of 1,4-anhydroerythritol showed a linear increase with temperature but C(2) of 1,4-anhydroerythritol showed a decrease between ca. 0 and ca. 55 deg C followed by an increase from ca. 55 to ca. 100 deg C.A multiligand complex was shown between 1,4-anhydroerythritol, water, and ammonium ion.The stoichiometry of the interaction between 1,4-anhydroerythritol, water, and aqueous ammonium ion was determined by nonlinear regression analysis applied to data obtained from 13C NMR chemical shifts through variation of temperature, solvent activity, aH2O(c,T), and solute activity, aNH4Cl(c,T).A general model was constructed for the dependence of the 13C NMR chemical shifts upon temperature and the activities of the two ligand species.
- Naugler, David G.,Cushley Robert J.
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p. 4720 - 4724
(2007/10/02)
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