Abstract
A catalytic amount of GaCl3 (5 mol%) was found to activate alkynyl glycosides effectively under mild reaction conditions to furnish a variety of O-glycosides in good yields with high β-selectivity.
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Tsuda T, Nakamura S, Hashimoto S (2004) Tetrahedron 60:10711
Toshima K, Tatsuta K (1993) Chem Rev 93:1503
Boons G-J (1996) Tetrahedron 52:1095
Khan SH, O’Neil RA (eds) (1996) Modern methods in carbohydrate synthesis. Harwood, Amsterdam
Ernst B, Hart GW, Sinay P (eds) (2000) Carbohydrates in chemistry and biology, part I. Wiley-VCH, Weinheim
Davis BG (2000) J Chem Soc Perkin Trans 1:2137
Demchenko AV (2003) Synlett 1225
Mukhopadhyay B, Field RA (2004) Carbohydr Res 339:1285
Kim IJ, Park TK, Hu S, Abrampah K, Zhang S, Livingston P, Danishefsky SJ (1995) J Org Chem 60:7716
Sarabia F, Martın-Ortiz L, Lopez-Herrera FJ (2003) Org Biomol Chem 21:3716
Wing C, Errey JC, Mukhopadhyay B, Blanchard JS, Field RA (2006) Org Biomol Chem 4:3945
Hotha S, Kashyap S (2006) J Org Chem 71:364
Nepogodiev SA, Dedola S, Marmuse L, Field RA (2007) Carbohydr Res 342:529
Bornaghi LF, Poulsen S-A (2005) Tetrahedron Lett 26:3485
Hotha S, Kashyap S (2006) J Am Chem Soc 128:9620
Kayastha AK, Hotha S (2012) Chem Commun 48:7161
Li Y, Yang X, Liu Y, Zhu C, Yang Y, Yu B (2010) Chem Eur J 16:1871
Chatani N, Inoue H, Kotsuma T, Murai S (2002) J Am Chem Soc 124:10294
Yamaguchi M, Tsukagoshi T, Arisawa M (1999) J Am Chem Soc 121:4074
Asao N, Asano T, Ohishi T, Yamamoto Y (2000) J Am Chem Soc 122:4817
Kobayashi K, Arisawa M, Yamaguchi M (2002) J Am Chem Soc 124:8528
Viswanathan GS, Wang M, Li C-J (2002) Angew Chem Int Ed 41:2138
Viswanathan GS, Li C-J (2002) Synlett 1553
Viswanathan GS, Li C-J (2002) Tetrahedron Lett 43:1613
Yadav JS, Reddy BVS, Chaya DN, Kumar GGKSN, Aravind S, Kunwar AC, Madavi C (2008) Tetrahedron Lett 49:3330
Reddy BVS, Reddy BB, Rao KVR, Yadav JS (2012) Tetrahedron Lett 53:2500
Yadav JS, Reddy BVS, Sengupta S, Biswas SK (2009) Synthesis 1301
Yadav JS, Reddy BVS, Gupta MK, Dash U, Pandey SK (2007) Synlett 809
Yadav JS, Reddy BVS, Bhasker EV, Raghvendra S, Narsaiah AV (2007) Tetrahedron Lett 48:677
Yadav JS, Reddy BVS, Gupta MK, Pandey SK (2007) J Mol Cat A Chem 264:309
Yadav JS, Reddy BVS, Eeshwaraiah B, Gupta MK, Biswas SK (2005) Tetrahedron Lett 46:1161
Yadav JS, Reddy BVS, Gupta MK, Biswas SK (2004) Synthesis 2711
Yadav JS, Reddy BVS, Padmavani B, Gupta MK (2004) Tetrahedron Lett 45:7577
Vankayalapati H, Singh G, Tranoy I (2001) Tetrahedron Asymmetry 12:1373
Vankayalapati H, Singh G, Tranoy I (1998) Chem Commun 19:2129
Buskas T, Soederberg E, Konradsson P, Fraser-Reid B (2000) J Org Chem 65:958
Sliedregt LAJM, Van Der Marel GA, Van Boom JH (1994) Proc Indian Acad Sci Chem Sci 106:1213
Spell M, Wang X, Wahba AE, Conner E, Ragains J (2013) Carbohydr Res 369:42
Nagai H, Sasaki K, Matsumura S, Toshima K (2005) Carbohydr Res 340:337
Charette AB, Cote B (1993) Tetrahedron Asymmetry 4:2283
Rodebaugh R, Fraser-Reid B (1996) Tetrahedron 52:7663
Wever WJ, Cinelli MA, Bowers AA (2013) Org Lett 15:30
Lu W, Navidpour L, Taylor SD (2005) Carbohydr Res 340:1213
Chitchirachan P, Pluempanupat W (2012) J Chem Chem Eng 6:778
Yamanoi T, Inoue R, Matsuda S, Hamasaki K (2008) Lett Org Chem 5:30
Kumar A, Geng Y, Schmidt RR (2012) Adv Synth Cat 354:1489
Thomas HG, Mieusset J-L (2008) Tetrahedron 64:5124
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NNY, MKG, and NS thank CSIR, New Delhi for the award of research fellowships.
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Yadav, J.S., Yadav, N.N., Gupta, M.K. et al. GaCl3-catalyzed activation of alkynyl glycosides for the synthesis of O-glycosides. Monatsh Chem 145, 517–520 (2014). https://doi.org/10.1007/s00706-013-1091-7
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DOI: https://doi.org/10.1007/s00706-013-1091-7