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P2O5-Al2O3 Catalyzed One Pot Acetylation, Benzylidene Acetal Protection and Benzylidene Removal of Sugar Derivatives
Corresponding Author(s) : Rajib Panchadhayee
Asian Journal of Chemistry,
Vol. 35 No. 6 (2023): Vol 35 Issue 6, 2023
Abstract
An environment-friendly, simple and efficient one-pot acetylation and benzylidene acetal formation procedure has been introduced for the synthesis of sugar derivatives using P2O5-Al2O3 as a solid acid catalyst under solvent-free condition at room temperature, with excellent overall yield. This benzylidene acetal has been deprotected using the same reagent but in a moist condition.
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- G.E. Ritchie, B.E. Moffatt, R.B. Sim, B.P. Morgan, R.A. Dwek and P.M. Rudd, Chem. Rev., 102, 305 (2002); https://doi.org/10.1021/cr990294a
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- P.M. Bhaskar and D. Loganathan, Synlett, 129 (1999); https://doi.org/10.1055/s-1999-2547
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- J. Xia and Y. Hui, Synth. Commun., 26, 881 (1996); https://doi.org/10.1080/00397919608003691
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References
G.E. Ritchie, B.E. Moffatt, R.B. Sim, B.P. Morgan, R.A. Dwek and P.M. Rudd, Chem. Rev., 102, 305 (2002); https://doi.org/10.1021/cr990294a
C.R. Bertozzi and L.L. Kiessling, Science, 291, 2357 (2001); https://doi.org/10.1126/science.1059820
K.C. Nicolaou and H.J. Mitchell, Angew. Chem. Int. Ed., 40, 1576 (2001); https://doi.org/10.1002/1521-3773(20010504)40:9<1576:AID-ANIE15760>3.0.CO;2-G
B.G. Davis, Chem. Rev., 102, 579 (2002); https://doi.org/10.1021/cr0004310
A.N. de Belder, Adv. Carbohydr. Chem. Biochem., 34, 179 (1977); https://doi.org/10.1016/S0065-2318(08)60325-X
J. Kihlberg, T. Frejd, K. Jansson and G. Magnusson, Carbohydr. Res., 152, 113 (1986); https://doi.org/10.1016/S0008-6215(00)90292-1
P.L. Barili, G. Berti, G. Catelani, F. Colonna and A. Marra, Tetrahedron Lett., 27, 2307 (1986); https://doi.org/10.1016/S0040-4039(00)84515-3
S.C. Hung and C.S. Chen, J. Chin. Chem. Soc., 47, 1257 (2000); https://doi.org/10.1002/jccs.200000173
R.G. Ault, W.N. Haworth and E.L. Hirst, J. Chem. Soc., 1012, 1012 (1935); https://doi.org/10.1039/jr9350001012
K. Freudenberg and R.M. Hixon, Ber. Dtsch. Chem. Ges. B, 56, 2119 (1923); https://doi.org/10.1002/cber.19230560909
F.M. Winnik, J.P. Carver and J.J. Krepinsky, J. Org. Chem., 47, 2701 (1982); https://doi.org/10.1021/jo00135a004
R. Panchadhayee and A.K. Misra, J. Carbohydr. Chem., 27, 148 (2008); https://doi.org/10.1080/07328300802030837
H.B. Wood Jr., H.W. Diehl and H.G. Fletcher Jr., J. Am. Chem. Soc., 79, 1986 (1957); https://doi.org/10.1021/ja01565a062
F.P. Boulineau and A. Wei, Carbohydr. Res., 334, 271 (2001); https://doi.org/10.1016/S0008-6215(01)00203-8
A. Liptak, J. Imre and P. Nanasi, Carbohydr. Res., 92, 154 (1981); https://doi.org/10.1016/S0008-6215(00)85991-1
B. Mukhopadhyay, D.A. Russell and R.A. Field, Carbohydr. Res., 340, 1075 (2005); https://doi.org/10.1016/j.carres.2005.02.012
B. Mukhopadhyay, Tetrahedron Lett., 47, 4337 (2006); https://doi.org/10.1016/j.tetlet.2006.04.118
C.S. Hudson and J.K. Dale, J. Am. Chem. Soc., 37, 1264 (1915); https://doi.org/10.1021/ja02170a025
B. Yu, J. Xie, S. Deng and Y.J. Hui, J. Am. Chem. Soc., 121, 12196 (1999); https://doi.org/10.1021/ja9926818
H. Binch, K. Stangier and J. Thiem, Carbohydr. Res., 306, 409 (1998); https://doi.org/10.1016/S0008-6215(97)10094-5
J.A. Hyatt and G.W. Tindall, Heterocycles, 35, 227 (1993); https://doi.org/10.3987/COM-92-S8
M.L. Wolfrom and A. Thompson, Carbohydr. Chem., 2, 211 (1963).
A. I. Vogel, Vogel’s Textbook of Practical Organic Chemistry, Wiley: New York, Edn. 5, pp. 644-651 (1989).
F. Dasgupta, P.P. Singh and H.C. Srivastava, Carbohydr. Res., 80, 346 (1980); https://doi.org/10.1016/S0008-6215(00)84876-4
J.C. Lee, C.A. Tai and S.C. Hung, Tetrahedron Lett., 43, 851 (2002); https://doi.org/10.1016/S0040-4039(01)02253-5
K.P.R. Kartha and R.A. Field, Tetrahedron, 53, 11753 (1997); https://doi.org/10.1016/S0040-4020(97)00742-4
A.A. Tai, S.S. Kulkarni and S.C. Hung, J. Org. Chem., 68, 8719 (2003); https://doi.org/10.1021/jo030073b
S. Ahmad and J. Iqbal, J. Chem. Soc. Chem. Commun., 114–115, 114 (1987); https://doi.org/10.1039/c39870000114
J.L. Montero, J.Y. Winum, A. Leydet, M. Kamal, A.A. Pavia and J.P. Roque, Carbohydr. Res., 297, 175 (1997); https://doi.org/10.1016/S0008-6215(96)00269-8
R. Ghosh, A. Chakraborty and S. Maiti, Tetrahedron Lett., 45, 9631 (2004); https://doi.org/10.1016/j.tetlet.2004.10.138
K.C. Lu, S.Y. Hsieh, L.N. Patkar, C.T. Chen and C.C. Lin, Tetrahedron, 60, 8967 (2004); https://doi.org/10.1016/j.tet.2004.06.138
A. Agarwal and Y.D. Vankar, Carbohydr. Res., 340, 1661 (2005); https://doi.org/10.1016/j.carres.2005.04.005
M.A. Zolfigol and A. Bamoniri, Synlett, 1621 (2002); https://doi.org/10.1055/s-2002-34230
P.M. Bhaskar and D. Loganathan, Tetrahedron Lett., 39, 2215 (1998); https://doi.org/10.1016/S0040-4039(98)00178-6
R. Kumareswaran, K. Pachamuthu and Y.D. Vankar, Synlett, 1652 (2000); https://doi.org/10.1055/s-2000-7925
K.S. Kim, Y.H. Song, B.H. Lee and C.S. Hahn, J. Org. Chem., 51, 404 (1986); https://doi.org/10.1021/jo00353a027
G. Mahender, R. Ramu, C. Ramesh and B. Das, Chem. Lett., 32, 734 (2003); https://doi.org/10.1246/cl.2003.734
P.M. Bhaskar and D. Loganathan, Synlett, 129 (1999); https://doi.org/10.1055/s-1999-2547
A.R. Hajipour, A. Zarei and A.E. Ruoho, Tetrahedron Lett., 48, 2881 (2007); https://doi.org/10.1016/j.tetlet.2007.02.090
M. Tatina, S.K. Yousuf and D. Mukherjee, Org. Biomol. Chem., 10, 5357 (2012); https://doi.org/10.1039/c2ob25452b
J. Xia and Y. Hui, Synth. Commun., 26, 881 (1996); https://doi.org/10.1080/00397919608003691
A. Santra, T. Ghosh and A.K. Misra, Beilstein J. Org. Chem., 9, 74 (2013); https://doi.org/10.3762/bjoc.9.9