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A Simple and Clean Method for O-Isopropylidenation of Carbohydrates
A Simple and Clean Method for O-Isopropylidenation of Carbohydrates
Bulletin of the Korean Chemical Society. 2014. Jul, 35(7): 2165-2168
Copyright © 2014, Korea Chemical Society
  • Received : January 04, 2014
  • Accepted : March 10, 2014
  • Published : July 20, 2014
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About the Authors
Yuan Wei Rong
Qi Hua Zhang
Wei Wang
Bao Lin Li

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Experimental Section
General Methods. Sulfonated polystyrene cation exchange resin CAT600 was donated by Xian Electric Power Resin Factory, China. It showed a parameter as the density of SO 3 H groups in 4.9-5.1 mmol/g, specific surface area in 35.0-38.5 m 2 /g, average pore size in 50-100 Å. Unless otherwise stated, other chemicals (AR) were purchased from commercial sources and used without purification. 1 H NMR spectra were recorded using CDCl 3 as a solvent on a Bruker Avance 300 MHz spectrometer (75 MHz for 13 C NMR). GC analysis was performed on a Shimadzu GC-2010 apparatus equipped with an Rxi-1MS capillary column (30 m × 0.25 mm × 0.25 μm) connected to a hydrogen flame ionization detector. The GC condition was used as follows: a sampling/ detector temperature of 250 ℃, a column temperature of 190 ℃, nitrogen as carrier gas, nitrogen pressure 100 kPa, total flow rate: 50 mL/min, hydrogen flow rate: 40 mL/min, air flow rate: 400 mL/min. The temperature programme: 190 ℃ for 3 min, then rose to 250 ℃ with the rate 10 ℃/min, finally held at 250 ℃ for 1 min.
General Procedure for the O-Isopropylidenation. To a suspension of the substrate (2 mmol) in dry acetone (10 mL), CAT600 (100 mg) was added. Then the mixture was stirred at 40 ℃ till the TLC ( n -hexane-EtOAc 2:1) showed the completion of the reaction. The catalyst was separated by filtration, washed with acetone, dried, and reused for a consecutive run under the same reaction conditions. The filtrate was condensed to dry in vacuum, and the residue was dissolved in CH 2 Cl 2 (10 mL) and washed with 3 × 5 mL brine. The organic layer was dried over anhydrous Na 2 SO 4 , filtered and evaporated to afford the crude product. Then the desired pure product was obtained by recrystallization from n -hexane. While, the silica gel column chromatography was used if the product existed in the liquid form.
Acknowledgements
The authors are thankful to financial support from the Natural Science Foundation of China (No. 21272144). References
References
Yamanoi T. , Oda Y. , Matsuda S. , Yamazaki I. , Matsumura K. , Katsuraya K. , Watanabe M. , Inazu T. 2006 Tetrahedron 62 10383 -    DOI : 10.1016/j.tet.2006.08.059
Veeneman G. H. , Boons G. J. 1998 In Carbohydrate Chemistry Blackie Academic & Professional London 141 -
Alam M. A. , Vankar Y. D. 2008 Tetrahedron Lett. 49 5534 -    DOI : 10.1016/j.tetlet.2008.07.057
Garegg P. J. , Hanessian S. 1997 In Preparative Carbohydrate Chemistry Marcel Dekker New York 3 -
Yadav V. K. , Agrawal D. 2007 Chem. Commun. (Cambridge) 48 5232 -
Gunter L. , Srefan P. 1986 Carbohydrate Research. 155 119 -    DOI : 10.1016/S0008-6215(00)90138-1
Goi A. , Bruzzese T. , Notarianni A. F. , Riva M. , Ronchini A. 1979 Arzneim.-Forsch./Drug Res. 29 986 -
Schmidt O. 1963 Methods Carbohydr. Chem. 2 318 -
Hering K. W. , Karaveg K. , Moremen K. W. , Pearson W. H. 2005 J. Org. Chem. 70 9892 -    DOI : 10.1021/jo0516382
Singh P. P. , Gharia M. M. , Dasgupta F. , Srivastava H. C. 1977 Tetrahedron Lett. 5 439 -
Lal B. , Gidwani R. M. , Rupp R. H. 1989 Synthesis 711 -
Schmid C. R. , Bryant J. D. , Dowlatzedah M. , Phillips J. L. , Prather D. E. , Schautz R. D. , Sear N. L. , Vianco C. S. 1991 J. Org. Chem. 56 4056 -    DOI : 10.1021/jo00012a049
Manzo E. , Barone G. , Parrilli M. 2000 Synlett 887 -
Lin C. C. , Jan M. D. , Weng S. S. , Lin C. C. , Chen C. T. 2006 Carbohydr. Res. 341 1948 -    DOI : 10.1016/j.carres.2006.04.001
Khan A. T. , Khan M. M. 2010 Carbohydr. Res. 345 154 -    DOI : 10.1016/j.carres.2009.09.017
Khan A. T. , Khan M. M. , Adhikary A. 2011 Carbohydr. Res. 346 673 -    DOI : 10.1016/j.carres.2010.12.018
Khiangte V. , Ghanashyam B. 2011 Tetrahedron Lett. 52 3759 -    DOI : 10.1016/j.tetlet.2011.05.050
Mandal S. , Verma P. R. , Mukhopadhyay B. , Gupta P. 2011 Carbohydr. Res. 346 2007 -    DOI : 10.1016/j.carres.2011.05.008
Rauter A. P. , Ramôa-Ribeiro F. , Fernandes A. C. , Figueiredo J. A. 1995 Tetrahedron 51 6529 -    DOI : 10.1016/0040-4020(95)00291-F
Asakura J. I. , Matsubara Y. , Yoshihara M. J. 1996 Carbohydr. Chem. 15 231 -    DOI : 10.1080/07328309608005441
Silvana P. , Annalisa G. , Daniele D. , Mauro D. N. , Giovanni P. 2006 Synthesis 305 -
Rajput V. K. , Mukhopadhyay B. 2006 Tetrahedron Lett. 47 5939 -    DOI : 10.1016/j.tetlet.2006.06.050
Pierluigi B. , Francesca L. 2009 Chem. Rev. 109 515 -    DOI : 10.1021/cr800404j
Sharma M. M. 1995 React. Funct. Polym. 26 3 -    DOI : 10.1016/1381-5148(95)00029-F
Christens G. M. 1962 J. Org. Chem. 27 1442 -    DOI : 10.1021/jo01051a507
Zheng Y. J. , Li J. , Lu J. J. , Jia Y. C. , Li B. L. 2013 Chemical Journal of Chinese Universities 34 2738 -
Amber O. , Christopher P. , Michael A. I. , Ian D. B. , Gregory A. S. , Martha D. M. , Michael B. S. 2011 Carbohydr. Res. 346 1662 -    DOI : 10.1016/j.carres.2011.04.017
Nadim S. S. , Kathrin J. , Matthias B. 2007 Organic Letters 9 5429 -    DOI : 10.1021/ol7021802