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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 42, 2012 - Issue 21
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Original Articles

Solvent-Free Preparation of 5-(α-D-Glucosyloxymethyl)furfural from Isomaltulose–Choline Chloride Melts

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Pages 3112-3116 | Received 21 Mar 2011, Published online: 17 Aug 2012

REFERENCES

  • Lichtenthaler , F. W. ; Mondel , S. Perspectives in the use of low-molecular-weight carbohydrates as organic raw materials . Pure Appl. Chem. 1997 , 69 ( 9 ), 1853 – 1866 .
  • Chheda , J. N. ; Huber , G. W. ; Dumesic , J. A. Liquid-phase catalytic processing of biomass-derived oxygenated hydrocarbons to fuels and chemicals . Angew. Chem. Internat. Ed. 2007 , 46 ( 38 ), 7164 – 7183 .
  • Bozell , J. J. ; Petersen , G. R. Technology development for the production of biobased products from biorefinery carbohydrates: The US Department of Energy's “Top 10” revisited . Green Chem. 2010 , 12 ( 4 ), 539 – 554 .
  • Antal , M. J. ; Mok , W. S. L. ; Richards , G. N. Mechanism of formation of 5-(hydroxymethyl)-2-furaldehyde from -fructose and sucrose . Carbohydr. Res. 1990 , 199 ( 1 ), 91 – 109 .
  • Sakurai , K. ; Yasuda , H. ; Makino , M. ; Ogiwara , H. ; Konno , S. Paratinose degradation products as deodorants for foods, beverages, oral compositions and, toiletry products. EP Patent 1062941 A2 , 2000 .
  • Lin , A. S. ; Qian , K. ; Usami , Y. ; Lin , L. ; Itokawa , H. ; Hsu , C. ; Morris-Natschke , S. L. ; Lee , K. H. 5-Hydroxymethyl-2-furfural, a clinical trials agent for sickle cell anemia, and its mono/di-glucosides from classically processed steamed Rehmanniae radix . J. Nat. Med. 2008 , 62 ( 2 ), 164 – 167 .
  • Adhikari , D. P. ; Schutzki , R. E. ; DeWitt , D. L. ; Nair , M. G. Effects of Amelanchier fruit isolates on cyclooxygenase enzymes and lipid peroxidation . Food Chem. 2006 , 97 ( 1 ), 56 – 64 .
  • Urashima , T. ; Suyama , K. ; Adachi , S. The condensation of 5-(hydroxymethyl)-2-furfuraldehyde with some aldoses on heating. Food Chem. 1988, 29 (1), 7–17.
  • Lichtenthaler , F. W. ; Martin , D. ; Weber , T. ; Schiweck , H. Studies on ketoses, 7–5-(α-D-Glucosyloxymethyl)furfural: Preparation from isomaltulose and exploration of its ensuing chemistry . Liebigs Ann. Chem. 1993 , 9 , 967 – 974 .
  • Lichtenthaler , F. W. Germany. EP 0 426 176 A2, 13 , 1991 .
  • Schiweck , H. ; Munir , M. ; Rapp , K. M. ; Schneider , B. ; Vogel , M. Zuckerind. (Berlin) 1990 , 115 , 555 – 565 .
  • Avalos , M. ; Babiano , R. ; Cintas , P. ; Jiménez , J. L. ; Palacios , J. C. Greener media in chemical synthesis and processing . Angew. Chem. Internat. Ed. 2006 , 45 ( 24 ), 3904 – 3908 .
  • Imperato , G. ; Eibler , E. ; Niedermaier , J. ; Konig , B. Low-melting sugar–urea–salt mixtures as solvents for Diels–Alder reactions . Chem. Commun. 2005 , ( 9 ), 1170 – 1172 .
  • Imperato , G. ; Hoger , S. ; Lenoir , D. ; Konig , B. Low melting sugar–urea–salt mixtures as solvents for organic reactions: Estimation of polarity and use in catalysis . Green Chem. 2006 , 8 ( 12 ), 1051 – 1055 .
  • Imperato , G. ; Vasold , R. ; König , B. Stille reactions with tetraalkylstannanes and phenyltrialkylstannanes in low melting sugar–urea–salt mixtures . Adv. Synth. Catal. 2006 , 348 ( 15 ), 2243 – 2247 .
  • Russ , C. ; Ilgen , F. ; Reil , C. ; Luff , C. ; Haji Begli , A. ; Koenig , B. Efficient preparation of [small beta]-d-glucosyl and [small beta]-d-mannosyl ureas and other N-glucosides in carbohydrate melts . Green Chem. 2011 , 13 , 156 – 161 .
  • Ilgen , F. ; Ott , D. ; Kralisch , D. ; Reil , C. ; Palmberger , A. ; Konig , B. Conversion of carbohydrates into 5-hydroxymethylfurfural in highly concentrated low melting mixtures . Green Chem. 2009 , 11 ( 12 ), 1948 – 1954 .
  • Hu , S. ; Zhang , Z. ; Zhou , Y. ; Song , J. ; Fan , H. ; Han , B. Direct conversion of inulin to 5-hydroxymethylfurfural in biorenewable ionic liquids . Green Chem. 2009 , 11 ( 6 ), 873 – 877 .
  • Kuster , B. F. M. 5-Hydroxymethylfurfural (HMF): A review focussing on its manufacture . Starch - Stärke 1990 , 42 ( 8 ), 314 – 321 .

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