Abstract
α-2-Deoxyglycosides were synthesized in ionic liquid ([bmim]BF4)by stereoselective glycosylation of endo-glycals with various o-nucleophiles in the presence of catalytic amount of pTSAin 71–95 % yield. High yields, easy recovery of the products, and reusable reaction medium (pTSA/IL couple) with consistent activity makes this protocol efficient and environmentally benign.
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He X, Agnihotri G, Liu H-W (2000) Chem Rev 100:4615
He XM, Liu HW (2002) Curr Opin Chem Biol 6:590
Rohr J, Thiericke P (1992) Nat Prod Rep 9:103
Weymouth-Wilson AC (1997) Nat Prod Rep 14:99
Costantino V, Imperatore C, Fattorusso E, Mangoni A (2000) Tetrahedron Lett 41:9177
Costantino V, Fattorusso E, Imperatore C, Mangoni A (2002) Tetrahedron Lett 43:9047
Lam SN, Gervay-Hague J (2003) Org Lett 5:4219
Bolitt V, Mioskowski C (1990) J Org Chem 55:5812
Colinas P, Bravo RD (2003) Org Lett 5:4509
Wandzik I, Bieg T (2006) Carbohydr Res 341:2702
Jaunzems J, Kashin D, Schonberger A, Kirschning A (2004) Eur J Org Chem :3435
Hou D, Lowary TL (2009) Carbohydr Res 344:1911
Sabesan S, Neira S (1991) J Org Chem 56:5468
Yadav JS, Reddy BVS, Reddy KB, Satyanarayana M (2002) Tetrahedron Lett 43:7009
Rani S, Agarwal A, Vankar YD (2003) Tetrahedron Lett 44:5001
Kolar C, Kneissl G (1990) Angew Chem Int Ed Engl 29:809
Kaila N, Blumenstein M, Bielawska H, Franck RW (1992) J Org Chem 57:4576
Toshima K, Nagai H, Ushiski Y, Matsumura S (1998) Synlett :1007
Pachamuthu K, Vankar YD (2001) J Org Chem 66:7511
Yadav JS, Subba Reddy BV, Vijaya Bhasker E, Raghavendra S, Narsaiah A (2007) Tetrahedron Lett 48:677
Sherry BD, Loy RN, Toste FD (2004) J Am Chem Soc 126:4510
Olivier-Bourbigou H, Magna L, Morvan D (2010) Appl Catal A Gen 373:1
Hallett JP, Welton T (2011) Chem Rev 111:3508
Sheldon RJ (2001) Chem Soc, Chem Commun 23:2399
Gordon CM (2001) Appl Catal A 222:101
Zimmermann HE, Wang PA (1993) J Am Chem Soc 115:2205
Rosatella AA, Frade RFM, Afonso CAM (2011) Curr Org Synth 8:840
Johnson KE, Pagni RM, Bartmess J (2007) Monatsh Chem 138:1077
Tasca JE, Ponzinibbio A, Díaz G, Bravo RD, Lavat A, González MG (2010) Top Catal 53:1087
Ponzinibbio A, Colinas PA, Lieberknecht A, Bravo RD (2006) Lett Org Chem 3:459
Colinas PA, Ponzinibbio A, Lieberknecht A, Bravo RD (2003) Tetrahedron Lett 44:7985
Baghernejad B (2011) pTSA was selected as the Brønsted acid for these experiments, envisioned as a robust, non-volatile, easy to manipulate and inexpensive solid. Curr Org Chem 15:3091
Fang D, Cheng J, Gong K, Shi Q-R, Zhou X-L, Liu Z-L (2008) J Fluor Chem 129:108
Szeje W, Fockt I (1989) Recl Trav Chim Pays-Bas 108:224
Hotha S, Tripathi A (2005) Tetrahedron Lett 46:4555
Agarwal A, Rani S, Vankar YD (2004) J Org Chem 69:6137
Wild R, Schmidt R (1995) Liebigs Ann 5:755
Bettelli E, Cherubini P, D‘Andrea P, Passacantilli P, Piancatelli G (1998) Tetrahedron 54:6011
Acknowledgments
Authors wish to thank Comisión de Investigaciones Científicas de la Provincia de Buenos Aires (CICPBA), UNLP and CONICET for their financial support to the present work. G.D. thanks CONICET for providing a doctoral research fellowship.
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Díaz, G., Ponzinibbio, A. & Bravo, R.D. pTSA/[bmim][BF4] Ionic Liquid: A Powerful Recyclable Catalytic System for the Synthesis of α-2-Deoxyglycosides. Top Catal 55, 644–648 (2012). https://doi.org/10.1007/s11244-012-9847-6
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DOI: https://doi.org/10.1007/s11244-012-9847-6