Crossref Cited-by Linking logo

Collect. Czech. Chem. Commun. 1974, 39, 1192-1209
https://doi.org/10.1135/cccc19741192

Preparation and the properties of 2,3-, 2,4-, and 3,4-dideoxy derivatives of 1,6-anhydro-β-D-glycero-hexopyranosuloses and corresponding alcohols

J. Pecka, J. Staněk, jr and M. Černý

Crossref Cited-by Linking

  • Jeřábek Vojtěch, Štejfa Vojtěch, Klajmon Martin, Řehák Karel: Thermodynamic Properties and Phase Equilibria of Dihydrolevoglucosenone and Its Mixtures with Hydrocarbons. J. Chem. Eng. Data 2023, 68, 3361. <https://doi.org/10.1021/acs.jced.3c00461>
  • Kong Dickson, Dolzhenko Anton V.: Cyrene: A bio-based sustainable solvent for organic synthesis. Sustainable Chemistry and Pharmacy 2022, 25, 100591. <https://doi.org/10.1016/j.scp.2021.100591>
  • Liu Xin, Pollard Brett, Banwell Martin G., Yu Li-Juan, Coote Michelle L., Gardiner Michael G., van Vugt-Lussenburg Barbara M. A., van der Burg Bart, Grasset Fabien L., Campillo Elisabeth, Sherwood James, Byrne Fergal P., Farmer Thomas J., Hutton Craig: Simple and modestly scalable synthesis of. Aust. J. Chem. 2022, 75, 331. <https://doi.org/10.1071/CH22046>
  • Quiquempoix Lucas, Wang Zhong, Graton Jérôme, Latchem Peter G., Light Mark, Le Questel Jean-Yves, Linclau Bruno: Synthesis of 2,3,4-Trideoxy-2,3,4-trifluoroglucose. J. Org. Chem. 2019, 84, 5899. <https://doi.org/10.1021/acs.joc.9b00310>
  • Ledingham Edward T., Greatrex Ben W.: Diastereoselective Weitz-Scheffer epoxidation of levoglucosenone for the synthesis of isolevoglucosenone and derivatives. Tetrahedron 2018, 74, 6107. <https://doi.org/10.1016/j.tet.2018.08.041>
  • Brel Valery K., Samet Aleksandr V., Konyushkin Leonid D., Stash Adam I., Belsky Vitaly K., Semenov Victor V.: Levoglucosenone-derived precursors for the stereoselective synthesis of methylene-expanded analogues of C-nucleosides. Mendeleev Communications 2015, 25, 44. <https://doi.org/10.1016/j.mencom.2015.01.016>
  • Ermolenko Mikhail S.: Convenient and Efficient Synthesis of 2,4-Dideoxy-levoglucosan. Synthetic Communications 2013, 43, 2841. <https://doi.org/10.1080/00397911.2012.745158>
  • Samet Alexander V., Lutov Dmitriy N., Konyushkin Leonid D., Strelenko Yuri A., Semenov Victor V.: Preparation of chiral cyclopropanecarboxylic acids and 3-oxabicyclo[3.1.0]hexane-2-ones from levoglucosenone. Tetrahedron: Asymmetry 2008, 19, 691. <https://doi.org/10.1016/j.tetasy.2008.02.016>
  • Kroutil Jiřı́, Černý Miloslav, Trnka Tomáš, Buděšı́nský Miloš: Synthesis of S-linked glucosaminyl-4-thiohex-2-enopyranosides via allylic SN2′ substitution of a tosylhexenose. Carbohydrate Research 2001, 334, 153. <https://doi.org/10.1016/S0008-6215(01)00175-6>
  • Belyk Kevin M., Leonard, William R., Bender Dean R., Hughes David L.: Practical Synthesis of 1,6-Anhydro-2,4-dideoxy-β-d-glycero- hexopyranos-3-ulose from Levoglucosan. J. Org. Chem. 2000, 65, 2588. <https://doi.org/10.1021/jo991719w>
  • Bartoš Petr, Černý Miloslav, Tišlerová Iva, Trnka Tomáš: Synthesis of Unsaturated Sulfur-Linked (1→4)-Disaccharides by Substitution of Tosyloxy Group in 1,6-Anhydro-3,4-dideoxy-2-O-tosyl-β-D-erythro-hex-3-enopyranose with 1-Thiohexopyranoses. Collect. Czech. Chem. Commun. 2000, 65, 1737. <https://doi.org/10.1135/cccc20001737>
  • Ton-That T.: Synthesis of Some Fully 3′ and 4′-C-Branched-Chain Sugar Nucleoside Analogues. Nucleosides and Nucleotides 1999, 18, 731. <https://doi.org/10.1080/15257779908041556>
  • Samet Alexander V., Niyazymbetov Murat E., Semenov Victor V., Laikhter Andrei L., Evans Dennis H.: Comparative Studies of Cathodically-Promoted and Base-Catalyzed Michael Addition Reactions of Levoglucosenone. J. Org. Chem. 1996, 61, 8786. <https://doi.org/10.1021/jo961019g>
  • Samet A. V., Laichter A. L., Reznikov D. N., Yamskov A. N., Ugrak B. I., Chernyshova N. B., Yolkin V. V., Semenov V. V.: Synthesis of heterocyclic systems with a carbohydrate fragment. Russ Chem Bull 1994, 43, 1073. <https://doi.org/10.1007/BF01558084>
  • Trnka Tomáš, Buděšínský Miloš, Černý Miloslav: Improved preparation of 1,6-anhydro-4-deoxy-2-O-p-toluenesulphonylβ-d-xylo-hexopyranose and of its d-[4-2H]gluco-analogue from 1,6 : 3,4-dianhydro-2-O-p-toluenesulphonyl-β-d-galactopyranose. Carbohydrate Research 1994, 259, 131. <https://doi.org/10.1016/0008-6215(94)84203-5>
  • Boquel P, Taillefumier C, Chapleur Y, Renaut P, Samreth S, Bellamy F.D: Towards a new type of HMG-CoA reductase inhibitors: Part II: Dramatic substituents effects in the C-5 epimerisation of carbohydrate derivatives. Tetrahedron 1993, 49, 83. <https://doi.org/10.1016/S0040-4020(01)80508-1>
  • Boquel P., Cazalet C.Loustau, Chapleur Y., Samreth S., Bellamy F.: An Expeditious Enantiospecific Synthesis of a Precursor of the Lactonic Portion of Mevinic Acids. Tetrahedron Letters 1992, 33, 1997. <https://doi.org/10.1016/0040-4039(92)88123-M>
  • Barton Derek H.R., Doo Ok Jang, Jaszberenyi Joseph Cs.: Tris(trimethylsilyl)silane and diphenylsilane in the radical chain dideoxygenation of 1,6-anhydro-D-glucose: A comparative study. Tetrahedron Letters 1992, 33, 6629. <https://doi.org/10.1016/S0040-4039(00)61003-1>
  • David C., Gesson J.P., Jacquesy J.C.: Mevinic acids and analogs : a novel efficient route to chiral synthons from 1,6-anhydro-D-glucose. Tetrahedron Letters 1989, 30, 6015. <https://doi.org/10.1016/S0040-4039(01)93842-0>
  • Okada Masahiko, Sumitomo Hiroshi, Ogasawara Ken: Chemical Synthesis of Polysaccharides III. A Synthetic Polysaccharide Having One Hydroxyl Group in Its Repeating Unit, 3,4-Dideoxy-(1→6)-α-DL-threo-hexopyranan. Polym J 1983, 15, 821. <https://doi.org/10.1295/polymj.15.821>
  • Toromanoff E.: Dynamic stereochemistry of the 5-, 6- and 7-membered rings using the torsion angle notation. Tetrahedron 1980, 36, 2809. <https://doi.org/10.1016/0040-4020(80)88015-X>
  • Jankowski K., Bélanger J., Söler F., Zamojski A.: Equation de Karplus appliquée à des systèmes sp2–sp3. Org. Magn. Reson. 1979, 12, 544. <https://doi.org/10.1002/mrc.1270120908>
  • Brimacombe John S., Hunedy Farouk, Mather Agnes M., Tucker Leslie C.N.: Studies related to the synthesis of derivatives of 2,6-diamino-2,3,4,6-tetradeoxy-D-erythro-hexose (purpurosamine C), a component of gentamicin C12. Carbohydrate Research 1979, 68, 231. <https://doi.org/10.1016/S0008-6215(00)83774-X>
  • Kelly Alan G., Roberts James S.: An improved synthesis of 1,6-anhydro-2,4-dideoxy-β-D-threo-hexopyranose. Carbohydrate Research 1979, 77, 231. <https://doi.org/10.1016/S0008-6215(00)83810-0>
  • Shafizadeh Fred, Furneaux Richard H., Stevenson Thomas T.: Some reactions of levoglucosenone. Carbohydrate Research 1979, 71, 169. <https://doi.org/10.1016/S0008-6215(00)86069-3>
  • Brimacombe John S., Hunedy Farouk, Tucker Leslie C.N.: The stereochemistry of the reduction of 1,6-anhydro-3,4-dideoxy-β-d-glycero-hex-3-enopyranos-2-ulose (levoglucosenone) with lithium aluminium hydride. Carbohydrate Research 1978, 60, C11. <https://doi.org/10.1016/S0008-6215(78)80052-4>
  • Paulsen Hans, Schnell Dagmar, Stenzel Wolfgang: Hydrazin‐Reaktionen, XIV. Reaktionen von Azido‐Zuckern mit Hydrazin. Chem. Ber. 1977, 110, 3707. <https://doi.org/10.1002/cber.19771101125>
  • Heyns Kurt, Soldat Wolf‐Dieter, Köll Peter: Über selektive katalytische Oxidationen, XXXV. Katalytische Oxidation der 2,7‐Anhydro‐β‐ D ‐ altro ‐2‐heptulopyranose („Sedoheptulosan”︁). Nachweis der 2,7‐Anhydro‐β‐ D ‐ arabino ‐2,5‐heptodiulopyranose. Chem. Ber. 1975, 108, 3611. <https://doi.org/10.1002/cber.19751081122>
  • Heyns Kurt, Rennecke Rolf‐Walter, Köll Peter: Optisch aktive Carbonylverbindungen mit 6,8‐Dioxabicyclo[3.2.1]octan‐System, I. Synthese der isomeren Epoxyketone aus der Reihe der 1,6‐Anhydro‐β‐ D ‐hexopyranosen. Chem. Ber. 1975, 108, 3645. <https://doi.org/10.1002/cber.19751081126>
  • Rennecke Rolf‐Walter, Eberstein Karsten, Köll Peter: Optisch aktive Carbonylverbindungen mit 6,8‐Dioxabicyclo[3.2.1]octan‐System, II. Synthese der isomeren 3‐Desoxyketone aus der Reihe der 1,6‐Anhydro‐β‐ D ‐hexopyranosen. Chem. Ber. 1975, 108, 3652. <https://doi.org/10.1002/cber.19751081127>
  • PECKA J., STANEK J. JUN., CERNY M.: ChemInform Abstract: SYNTHESES WITH ANHYDRO SUGARS PART 19, PREPARATION AND THE PROPERTIES OF 2,3‐, 2,4‐, AND 3,4‐DIDEOXY DERIVATIVES OF 1,6‐ANHYDRO‐BETA‐D‐GLYCERO‐HEXOPYRANOSULOSES AND CORRESPONDING ALCOHOLS. Chemischer Informationsdienst 1974, 5. <https://doi.org/10.1002/chin.197430429>