Catalysis and deactivation of montmorillonite
K10 in the aryl O -glycosylation
of glycosyl trichloroacetoimidates

doi:10.1007/s11705-009-0279-1

Front. Chem. Sci. Eng.

2010, Vol. 4

Issue (3) : 342-347 https://doi.org/10.1007/s11705-009-0279-1

Research articles

Catalysis and deactivation of montmorillonite K10 in the aryl O -glycosylation of glycosyl trichloroacetoimidates

Xiaoliu LI,Xinhao YAN,Zhiwei LI,Hua CHEN,Pingzhu ZHANG,

Key Laboratory of Chemical Biology of Hebei Province, College of Chemistry and Environmental Science, Hebei University, Baoding 071002, China;

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Abstract The catalysis of montmorillonite K10 (MK10) for aryl O-glycosylation of glycosyl trichloroacetimidates was investigated. It was found that the catalyst MK10 is deactivated gradually in the recycle glycosylation. The fresh and the deactivated catalysts were characterized by X-ray diffraction (XRD), X-ray photoelectron spectroscopy (XPS), Thermogravimetric analysis (TGA), and N₂ adsorption-desorption. The results show that the eliminated trichloroacetamide molecule deposits on the MK10, which blocks and poisons the active sites, resulting in the deactivation of the catalyst. The regeneration of the deactivated MK10 by calcination was studied preliminarily.

Issue Date: 05 September 2010

Cite this article:

Xinhao YAN,Xiaoliu LI,Zhiwei LI, et al. Catalysis and deactivation of montmorillonite K10 in the aryl O -glycosylation of glycosyl trichloroacetoimidates[J]. Front. Chem. Sci. Eng., 2010, 4(3): 342-347.

URL:

https://academic.hep.com.cn/fcse/EN/10.1007/s11705-009-0279-1
https://academic.hep.com.cn/fcse/EN/Y2010/V4/I3/342

	Toshima K, Tatsuta K. Recent progress in O-glycosylation methods and its application to natural products synthesis. Chem Rev, 1993, 93: 1503–1531 doi: 10.1021/cr00020a006
	Jensen K J. O-Glycosylations under neutral or basic conditions. J Chem Soc Perkin Trans 1, 2002, 2219–2233 doi: 10.1039/b110071h
	Pellissier H. Use of O-glycosylation in total synthesis. Tetrahedron, 2005, 61: 2947–2993 doi: 10.1016/j.tet.2005.01.070
	Jacobsson M, Malmberg J, Ellervik U. Aromatic O-glycosylation. Carbohydr Res, 2006, 341: 1266–1281 doi: 10.1016/j.carres.2006.04.004
	Mahling J A, Schmidt R R. Aryl C-glycosides from O-glycosyltrichloroacetimidates and phenolderivatives with trimethylsilyl trifluoromethanesulfonate (TMSOTf)as the catalyst. Synthesis, 1993, 325–328 doi: 10.1055/s-1993-25859
	Hasuoka A, Nakayama Y, Adachi M, Kamiguchi H, Kamiyama K. Development of a stereoselective practical synthetic route to Indolmycin, a candidateanti-H pylori agent. Chem Pharm Bull, 2001, 49: 1604–1608 doi: 10.1248/cpb.49.1604
	Du Y, Wie G, Linhardt R J. The first total synthesisof calabricoside A. Tetrahedron Lett, 2003, 44: 6887–6890 doi: 10.1016/S0040-4039(03)01706-4
	B?hm G, Waldmann H. O-glycoside synthesis under neutral conditionsin concentrated solutions of LiClO₄ in organic solvents employing benzyl-protected glycosyl donors. Liebigs Ann, 1996, 613–619
	Matsumoto T, Katsuki M, Suzuki K. Rapid O-glycosidation of phenols with glycosyl fluoride by usingthe combinational activator, Cp₂HfCl₂-AgClO₄. Chem Lett, 1989, 437–440 doi: 10.1246/cl.1989.437
	Yamaguchi M, Horiguchi A, Fukuda A, Minami T. Novel synthesis of aryl 2,3,4,6-tetra-O-acetyl-D-glucopyranosides. J Chem Soc Perkin Trans1, 1990, 1079–1082 doi: 10.1039/p19900001079
	Smits E, Engberts J B F N, Kellogg R M, Van Doren H A. Reliable method for the synthesis of aryl β-D-glucopyranosides, using boron trifluoride-diethyl ether as catalyst. J Chem Soc Perkin Trans 1, 1996, 2873–2877 doi: 10.1039/p19960002873
	Yamanoi T, Fujioka A, Inazu T. New synthetic methods andreagents for complex carbohydrates. IX. aryl D-glucopyranosides and 1-aryl-1-deoxy-D-glucopyranoses from 2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl dimethylphosphinothioate. Bull Chem Soc Jpn, 1994, 66: 1488–1491 doi: 10.1246/bcsj.67.1488
	Kometani T, Kondo H, Fujimori Y. Boron trifluoride-catalyzed rearrangementof 2-aryloxytetrahydropyrans: a new entry to C-arylglycosidation. Synthesis, 1988, 1005–1007 doi: 10.1055/s-1988-27788
	Matsumoto T, Katsuki K, Suzuki K. New approach to C-aryl glycosides starting from phenol andglycosyl fluoride. Lewis acid-catalyzed rearrangement of O-glycoside to C-glycoside. Tetrahedron Lett, 1988, 29: 6935–6938 doi: 10.1016/S0040-4039(00)88479-8
	Cornélis A, Laszlo P, Zettler M W. Montmorillonite K10. In: Reich H J, Rigby J H, eds. Handbook of reagents for organic synthesis: acidic and basic reagents. Chichester: John Wiley & Sons, 1999, 262–265
	Toshima K, Nagai H, Kasumi K, Kawahara K, Matsumura S. Stereocontrolled glycosidationsusing a heterogeneous solid acid, sulfated zirconia, for the directsyntheses of α- and β-manno- and 2-deoxyglucopyranosides. Tetrahedron, 2004, 60: 5331–5339 doi: 10.1016/j.tet.2004.04.071
	Oikawa M, Tanaka T, Fukuda N, Kusumoto S. One-pot preparation and activation of glycosyl trichloroacetimidates:operationally simple glycosylation induced by combined use of solid-supported,reactivity-opposing reagents. Tetrahedron Lett, 2004, 45: 4039–4042 doi: 10.1016/j.tetlet.2004.03.170
	Jagath R G, Latha D, Thirupathaiah C, Srinivasa R K. A facile synthesis of 2,3-disubstituted-6-arylpyridinesfrom enaminones using montmorillonite K10 as solid acid support. Tetrahedron Lett, 2005, 46: 301–302 doi: 10.1016/j.tetlet.2004.11.071
	Bahulayan D, Das S K, Iqbal J. Montmorillonite K10 clay: an efficientcatalyst for the one-pot stereoselective synthesis of beta-acetamidoketones. J Org Chem, 2003, 68: 5735–5738 doi: 10.1021/jo020734p
	Kantevari S, Vuppalapati S V N, Nagarapu L. Montmorillonite K10 catalyzed efficient synthesis of amidoalkyl naphthols under solvent free conditions. Catal Commun, 2007, 8: 1857–1862 doi: 10.1016/j.catcom.2007.02.022
	Dintzner M R, McClelland K M, Morse K M, Akroush M H. Montmorillonite clays in organic synthesis: a one-potconversion of phenols to 2,2-dimethylbenzopyrans. Synlett, 2004, 2028–2030 doi: 10.1055/s-2004-830865
	Clark J H, Macquarrie D J. Environmentally friendly catalytic methods. Chem Soc Rev, 1996, 25: 303–310 doi: 10.1039/cs9962500303
	Laszlo P. Catalysis of organic reactions by inorganic solids. Pure Appl Chem, 1990, 62: 2027–2030 doi: 10.1351/pac199062102027
	Nagai H, Sasaki K, Matsumura S, Toshima K. Environmentally benign β-stereoselective glycosidations of glycosyl phosphites using a reusableheterogeneous solid acid, montmorillonite K-10. Carbohydr Res, 2005, 340: 337–353 doi: 10.1016/j.carres.2004.11.025
	Fügedi P. Glycosylation Methods. In: Daniel E L, Péter F, eds. The Organic Chemistry of Sugars. Boca Raton: Taylor & Francis Group, 2006, 86–176
	Toshima K. Glycosyl Halides. In: Fraser-Reid B O, Tatsuta K, Thiem J, eds. Glycoscience: Chemistry and Chemical Biology, 2nd ed. Berlin: Springer-Verlag, 2008, 429–450 doi: 10.1007/978-3-540-30429-6_10
	Shanmugasundaram B, Bose A K, Balasubramanian K K Microwave-induced montmorillonite K10-catalyzed Ferrier rearrangement of tri-O-acetyl-d-galactal: mild, eco-friendly, rapid glycosidation with allylic rearrangement. Tetrahedron Lett, 2002, 43: 6795–6798 doi: 10.1016/S0040-4039(02)01517-4
	Brimble M A, Davey R M, McLeod M D, Murphy M. C-glycosylation of oxygenated naphthols with3-dimethylamino-2,3,6-trideoxy-L-arabino-hexopyranose and 3-azido-2,3,6-trideoxy-D- arabino-hexopyranose. Austral J Chem, 2003, 56: 787–794 doi: 10.1071/CH02236
	Schmidt R R, Michael J. Facile synthesis of α- and β-O-glycosyl imidates: preparation of glycosides and disaccharides. Angew Chem Int Eng Ed, 1980, 19: 731–732 doi: 10.1002/anie.198007311
	Clark J H, Cullen S R, Barlow S J, Bastock T W. Environmentally friendly chemistry using supported reagentcatalysts: structure-property relationships for clayzic. J Chem Soc Perkin Trans 2, 1994, 1117–1130 doi: 10.1039/p29940001117
	Onaka M, Shinoda T, Izumi Y, Nolen E. Porphyrin synthesis in clay nanospaces. Chem Lett, 1993, 117–120 doi: 10.1246/cl.1993.117
	Yadav G D, Asthana N S, Kamble V S. Cesium-substituted dodecatungstophosphoricacid on K-10 clay for benzoylation of anisole with benzoyl chloride. J Catal, 2003, 217: 88–99
	Kim Y, Lee J S, Rhee C H, Kim H K, Chang H. Montmorillonite functionalizedwith perfluorinated sulfonic acid for proton-conducting organic-inorganiccomposite membranes. J Power Sources, 2006, 162: 180–185 doi: 10.1016/j.jpowsour.2006.07.041
	Seyama H, Soma M. Bonding-state characterization of the constituent elements of silicate mineralsby X-ray photoelectron spectroscopy. J Chem Soc Faraday Trans 1, 1985, 81: 485–495 doi: 10.1039/f19858100485

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