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Pure Appl. Chem., 1993, Vol. 65, No. 4, pp. 779-786

http://dx.doi.org/10.1351/pac199365040779

The chemistry of N-pentenyl glycosides: Synthetic, theoretical, and mechanistic ramifications

B. Fraser-Reid, J. R. Merritt, A. L. Handlon and C. Webster Andrews

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  • Kumar Rishi, Whitfield Dennis M.: Could Diastereoselectivity in the Presence of O-2 Chiral Nonparticipating Groups Be an Indicator of Glycopyranosyl Oxacarbenium Ions in Glycosylation Reactions?. J Org Chern 2012, 77, 3724. <http://dx.doi.org/10.1021/jo202563f>
  • Phan Hung Duy, Yokoyama Tomoya, Matsumoto Yuji: Direct participation of counter anion in acid hydrolysis of glycoside. Org. Biomol. Chem. 2012, 10, 7382. <http://dx.doi.org/10.1039/c2ob25451d>
  • FRASER-REID B., MERRITT J. R., HANDLON A. L., ANDREWS C. W.: ChemInform Abstract: The Chemistry of N-Pentenyl Glycosides: Synthetic, Theoretical, and Mechanistic Ramifications. ChemInform 2010, 24, no. <http://dx.doi.org/10.1002/chin.199326306>
  • Keyari Charles M., Polt Robin: Serine and Threonine Schiff Base Esters React with β-Anomeric Peracetates in the Presence of BF3·Et2O to Produce β-Glycosides. J Carbohydr Chem 2010, 29, 181. <http://dx.doi.org/10.1080/07328303.2010.508295>
  • Ionescu Andrei R., Whitfield Dennis M., Zgierski Marek Z.: O-2 Substituted pyranosyl oxacarbenium ions are C-2–O-2 2-fold rotors with a strong syn preference. Carbohydrates Research 2007, 342, 2793. <http://dx.doi.org/10.1016/j.carres.2007.09.007>
  • Fraser-Reid Bert, Lu Jun, Jayaprakash K.N., López J. Cristóbal: Synthesis of a 28-mer oligosaccharide core of Mycobacterial lipoarabinomannan (LAM) requires only two n-pentenyl orthoester progenitors. Tet Asymm 2006, 17, 2449. <http://dx.doi.org/10.1016/j.tetasy.2006.09.008>
  • Lafont Dominique, Boullanger Paul: Syntheses of l-glucosamine donors for 1,2-trans-glycosylation reactions. Tet Asymm 2006, 17, 3368. <http://dx.doi.org/10.1016/j.tetasy.2006.12.011>
  • Nukada Tomoo, Bérces Attila, Wang LiJie, Zgierski Marek Z., Whitfield Dennis M.: The two-conformer hypothesis: 2,3,4,6-tetra-O-methyl-mannopyranosyl and -glucopyranosyl oxacarbenium ions. Carbohydrates Research 2005, 340, 841. <http://dx.doi.org/10.1016/j.carres.2004.12.021>
  • Mei Xiangdong, Heng Linsen, Fu Mingkun, Li Zhimin, Ning Jun: Synthesis of β-d-Glcp-(1→3)-[β-d-Glcp-(1→6)]-β-d-Glcp-(1→3)-β-d-Glcp-(1→6)-[β-d-Galp-(1→4)-β-d-Glcp-(1→3)]-β-d-GlcpOLauryl, an oligosaccharide with anti-tumor activity. Carbohydrates Research 2005, 340, 2345. <http://dx.doi.org/10.1016/j.carres.2005.08.010>
  • Lafont Dominique, Boullanger Paul, Carvalho Francine, Vottero Philippe: A convenient access to β-glycosides of N-acetyllactosamine. Carbohydrates Research 1997, 297, 117. <http://dx.doi.org/10.1016/S0008-6215(96)00263-7>