Toward Green and Sustainable Chemical Glycosylation: Enhanced Lewis Acidity of Recyclable Solid Super Acid Catalyst, SO₄/ZrO₂ by CaCl₂ Doping

REFERENCES

• Fischer , E. 1893 . Ueber die Glucoside der Alkohole . Ber. Dtsch. Chem. Ges. , 26 : 2400 – 2412 .
   Google Scholar
• Toshima , K. and Tatsuta , K. 1993 . Recent progress in O-glycosylation methods and its application to natural products synthesis . Chem. Rev. , 93 : 1503 – 1531 .
   Web of Science ®Google Scholar
• Schmidt , R. R. and Kinzy , W. 1994 . Anomeric-oxygen activation for glycoside synthesis: the trichloroacetimidate method . Adv. Carbohydr. Chem. Biochem. , 50 : 21 – 123 .
   PubMed Web of Science ®Google Scholar
• Davis , B. G. 2000 . Recent developments in oligosaccharide synthesis . J. Chem. Soc. Perkin Trans. , 1 : 2137 – 2160 .
   Google Scholar
• Dwek , R. A. 1996 . Glycobiology: toward understanding the function of sugars . Chem. Rev. , 96 : 683 – 720 .
   PubMed Web of Science ®Google Scholar
• Lütteke , T. 2008 . Web resources for the glycoscientist . Chem. Bio. Chem. , 9 : 2155 – 2160 .
   Google Scholar
• Nakahara , T. , Hashimoto , R. , Nakagawa , H. , Monde , K. , Miura , N. and Nishimura , S.-I. 2008 . Glycoconjugate Data Bank: structures an annotated glycan structure database and N-glycan primary structure verification service . Nucleic Acid Res. , 36 : D368 – D371 .
   PubMedGoogle Scholar
• For example, see: (a) , Jessop , P. G. , Ikariya , T. and Noyori , R. 1994 . Homogeneous catalytic hydrogenation of supercritical carbon dioxide . Nature , 368 : 231 – 233 .
   Google Scholar
• Collins , T. 2001 . Toward sustainable chemistry . Science , 291 : 48 – 49 .
   PubMed Web of Science ®Google Scholar
• Curzons , A. D. , Constable , D. J.C. , Mortimer , D. N. and Cunningham , V. L. 2001 . So you think your process is green, how do you know?—using principles of sustainability to determine what is green–a corporate perspective . Green Chem. , 3 : 1 – 6 .
   Web of Science ®Google Scholar
• Hino , M. , Kobayashi , S. and Arata , K. 1979 . Solid catalyst treated with anion. 2. Reactions of butane and isobutane catalyzed by zirconium oxide treated with sulfate ion. Solid superacid catalyst . J. Am. Chem. Soc. , 101 : 6439 – 6441 .
   Web of Science ®Google Scholar
• Hino , M and Arata , K. 1980 . Synthesis of solid superacid catalyst with acid strength of He <-16.04 . J. Chem. Soc. Chem. Commun. , : 851 – 852 .
   Google Scholar
• Yadav , G. D. and Nair , J. J. 1999 . Sulfated zirconia and its modified versions as promising catalysts for industrial processes . Microporous Mater. , 33 : 1 – 48 .
   Google Scholar
• Reddr , B. M. and Patil , M. K. 2009 . Organic syntheses and transformations catalyzed by sulfated zirconia . Chem. Rev. , 109 : 2185 – 2208 .
   PubMed Web of Science ®Google Scholar
• Toshima , K. , Kasumi , K. and Matsumura , S. 1998 . Novel stereocontrolled glycosidations using a solid acid, SO4/ZrO2, for direct syntheses of α- and β-mannopyranosides . Synlett , : 643 – 645 .
   Web of Science ®Google Scholar
• Toshima , K. , Kasumi , K. and Matsumura , S. 1999 . Novel stereocontrolled glycosidations of 2-deoxyglucopyranosyl fluoride using a heterogeneous solid acid, sulfated zirconia (SO4/ZrO2) . Synlett , : 813 – 815 .
   Web of Science ®Google Scholar
• Toshima , K. , Nagai , H. and Matsumura , S. 1999 . Novel dehydrative glycosidations of 1-hydroxy sugars using a heteropoly acid . Synlett , : 1420 – 1422 .
   Web of Science ®Google Scholar
• Toshima , K. , Nagai , H. , Kasumi , K. , Kawahara , K. and Matsumura , S. 2004 . Stereocontrolled glycosidations using a heterogeneous solid acid, sulfated zirconia, for the direct syntheses of α- and β-manno- and 2-deoxyglucopyranosides . Tetrahedron , 60 : 5331 – 5339 .
   Web of Science ®Google Scholar
• Li , X.-B. , Ogawa , M. , Monden , T. , Maeda , T , Yamashita , E. , Naka , M. , Matsuda , M. , Hinou , H. and Nishimura , S.-I. 2006 . Glycosidation promoted by a reusable solid superacid in supercritical carbon dioxide . Angew. Chem. Int. Ed. , : 5652 – 5655 .
   PubMed Web of Science ®Google Scholar
• Hinou , H. , Saito , N. , Ogawa , M. , Maeda , T. and Nishimura , S.-I. 2009 . Microwave effect for glycosylation promoted by solid super acid in supercritical carbon dioxide . Int. J. Mol. Sci. , 10 : 5285 – 5295 .
   PubMed Web of Science ®Google Scholar
• Florent , J.-C. and Monneret , C. 1987 . Stereocontrolled route to 3-amino-2,3,6- trideoxy-hexopyranoses. K-10 montmorillonite as a glycosidation reagent for acosaminide synthesis . J. Chem. Soc., Chem. Commun. , : 1171 – 1172 .
   Google Scholar
• Toshima , K. , Ishizuka , T. , Matsuo , G. and Nakata , M. 1995 . Practical glycosidation method of glycals using montmorillonite K-10 as an environmentally acceptable and inexpensive industrial catalyst . Synlett , : 306 – 308 .
   Web of Science ®Google Scholar
• Toshima , K. , Miyamoto , N. , Matsuo , G. , Nakata , M. and Matsumura , S. 1996 . Environmentally compatible C-glycosidation of glycals using montmorillonite K-10 . Chem. Commun. , : 1379 – 1380 .
   Web of Science ®Google Scholar
• Sasaki , K. , Matsumura , S. and Toshima , K. 2004 . A novel glycosidation of glycosyl fluoride using a designed ionic liquid and its effect on the stereoselectivity . Tetrahedron Lett. , 45 : 7043 – 7047 .
   Web of Science ®Google Scholar
• Nagai , H. , Sasaki , K. , Matsumura , S. and Toshima , K. 2005 . Environmentally benign β-stereoselective glycosidations of glycosyl phosphites using a reusable heterogeneous solid acid, montmorillonite K-10 . Carbohydr. Res. , 340 : 337 – 353 .
   PubMed Web of Science ®Google Scholar
• Adinolfi , M. , Barone , G. , Iadonisi , A. and Schiattarella , M. 2002 . Iodine triethylsilane as a convenient promoter system for the activation of disarmed glycosyl trichloro- and N-(phenyl)trifluoroacetimidates . Synlett , : 269 – 270 .
   Web of Science ®Google Scholar
• Adinolfi , M. , Barone , G. , Iadonisi , A. and Schiattarella , M. 2002 . Efficient activation of glycosyl N-(phenyl)trifluoroacetimidate donors with ytterbium(III) triflate in the glycosylation reaction . Tetrahedron Lett. , 43 : 5573 – 5577 .
   Web of Science ®Google Scholar
• Mukhopadhyay , B. , Maurer , S. V. , Rudolph , N. , Van Well , R. M. , Russell , D. A. and Field , R. A. 2005 . From solution phase to “on-column” chemistry: trichloroacetimidate-based glycosylation promoted by perchloric acid-silica . J. Org. Chem. , 70 : 9059 – 9062 .
   PubMed Web of Science ®Google Scholar
• Adinolfi , M. , Barone , G. , Iadonisi , A. and Schiattarella , M. 2003 . Activation of glycoyl trihaloacetimidates with acid-washed molecular sieves in the glycosidation reaction . Org. Lett. , 5 : 987 – 989 .
   PubMed Web of Science ®Google Scholar
• Adinolfi , M. , Iadonisi , A. , Ravida , A. and Schiattarella , M. 2005 . Versatile use of ytterbium(III) triflate and acid washed molecular sieves in the activation of glycosyl trifluoroacetimidate donors. Assemblage of a biologically relevant tetrasaccharide sequence of Globo H . J. Org. Chem. , 70 : 5316 – 5319 .
   PubMed Web of Science ®Google Scholar
• Sohn , J. R. , Lee , S. H. and Lim , J. S. 2006 . New solid superacid catalyst prepared by doping ZrO2 with Ce and modifying with sulfate and its catalytic activity for acid catalysis . Catal. Today. , 116 : 143 – 150 .
   Web of Science ®Google Scholar
• Nishimura , S. –I. and Matsuda , M. 1997 . Discovery and development of novel glycosidation reaction using solid superacid catalyst (SO4/ZrO2) . Abstracts of XIX^th Japanese Carbohydrate Symposium , : 55
   Google Scholar
• Schmidt , R. R. and Michel , J. 1985 . O-(α-D-glucopyranosyl)trichloroacetimidate as a glucosyl donor . J. Carbohydr. Chem. , 4 : 141 – 169 .
   Web of Science ®Google Scholar
• Schmidt , R. R. 2008 . Glycoscience , 2nd ed. , 451 – 524 . Heidelberg : Springer Verlag GmbH .
   Google Scholar
• Shannon , R. D. 1976 . Revised effective ionic radii and systematic studies of interatomic distances in halides and chalcogenides . Acta Cryst. , A32 : 751 – 767 .
   Web of Science ®Google Scholar
• Kapustin , G. I. , Brueva , T. R. , Klyachko , A. L. , Beran , S. and Wichterlova , B. 1988 . Determination of the number and acid strength of acid sites in zeolites by ammonia adsorption: comparison of calorimetry and temperature-programmed desorption of ammonia . Appl. Catalysis , 42 : 239 – 246 .
   Google Scholar
• Emeis , C. A. 1993 . Determination of integrated molar extinction coefficients for IR. Absorption bands of pyridine adsorbed on solid acid catalysts . J. Catal. , 141 : 347 – 354 .
   Web of Science ®Google Scholar