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Pure Appl. Chem., 2000, Vol. 72, No. 9, pp. 1577-1588

http://dx.doi.org/10.1351/pac200072091577

Formylation of carbohydrates and the evolution of synthetic routes to artificial oligosaccharides and glycoconjugates

Alessandro Dondoni

Laboratorio di Chimica Organica, Dipartimento di Chimica, Università di Ferrara, Via Borsari 46, 44100 Ferrara, Italy

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  • Sipos Szabolcs, Jablonkai István, Egyed Orsolya, Czugler Mátyás: Preparation of 2-amino-2-C-glycosyl-acetonitriles from C-glycosyl aldehydes by Strecker reaction. Carbohydrates Research 2011, 346, 2862. <http://dx.doi.org/10.1016/j.carres.2011.10.023>
  • Bouché Léa, Reissig Hans-Ulrich: Synthesis of novel carbohydrate mimetics via 1,2-oxazines. PureAppl Chem 2011, 1. <http://dx.doi.org/10.1351/PAC-CON-11-09-20>
  • Dondoni Alessandro: ChemInform Abstract: Formylation of Carbohydrates and the Evolution of Synthetic Routes to Artificial Oligosaccharides and Glycoconjugates. ChemInform 2010, 32, no. <http://dx.doi.org/10.1002/chin.200122244>
  • Kolympadi Maria, Fontanella Marco, Venturi Chiara, André Sabine, Gabius Hans-Joachim, Jiménez-Barbero Jesús, Vogel Pierre: Synthesis and Conformational Analysis of (α-D-Galactosyl)phenylmethane and α-,β-Difluoromethane Analogues: Interactions with the Plant Lectin Viscumin. Chem Eur J 2009, 15, 2861. <http://dx.doi.org/10.1002/chem.200801394>
  • Castagnolo Daniele, Botta Lorenzo, Botta Maurizio: One-pot multicomponent synthesis of 2,3-dihydropyrans: new access to furanose–pyranose 1,3-C–C-linked-disaccharides. Tetrahetron Lett 2009, 50, 1526. <http://dx.doi.org/10.1016/j.tetlet.2009.01.047>
  • Ducatti Diogo R. B., Massi Alessandro, Noseda Miguel D., Duarte Maria Eugênia R., Dondoni Alessandro: Production of carbohydrate building blocks from red seaweed polysaccharides. Efficient conversion of galactans into C-glycosyl aldehydes. Org Biomol Chem 2009, 7, 576. <http://dx.doi.org/10.1039/b816606d>
  • Kirschning Andreas, Kujat Christof, Luiken Silke, Schaumann Ernst: Small and Versatile – Formyl Anion and Dianion Equivalents. Eur J Org Chem 2007, 2007, 2387. <http://dx.doi.org/10.1002/ejoc.200601003>
  • Namme Rie, Mitsugi Takashi, Takahashi Hideyo, Shiro Moto, Ikegami Shiro: Synthesis of 1-deoxyhept-2-ulosyl-glycono-1,5-lactone utilizing α-selective O-glycosidation of 2,6-anhydro-1-deoxy-d-hept-1-enitols. Tetrahedron 2006, 62, 9183. <http://dx.doi.org/10.1016/j.tet.2006.07.032>
  • Komiotis Dimitri, Agelis George, Manta Stella, Tzioumaki Niki, Tsoukala Evangelia, Antonakis Kostas: A Facile, One‐Step Conversion of 6‐O‐Trityl and 6‐O‐TBDMS Monosaccharides into the Corresponding Formate Esters. J Carbohydr Chem 2006, 25, 441. <http://dx.doi.org/10.1080/07328300600859668>
  • Dondoni Alessandro, Massi Alessandro, Sabbatini Simona: Multiple Component Approaches to C-Glycosyl β-Amino Acids by Complementary One-Pot Mannich-Type and Reformatsky-Type Reactions. Chem Eur J 2005, 11, 7110. <http://dx.doi.org/10.1002/chem.200500823>
  • Helms Matthias, Schade Wolfgang, Pulz Robert, Watanabe Toshiko, Al-Harrasi Ahmed, Fišera Lubor, Hlobilová Iva, Zahn Gernot, Reißig Hans-Ulrich: Stereodivergent Syntheses of Highly Substituted Enantiopure 4-Alkoxy-3,6-dihydro-2H-1,2-oxazines by Addition of Lithiated Alkoxyallenes to Carbohydrate-Derived Aldonitrones. Eur J Org Chem 2005, 2005, 1003. <http://dx.doi.org/10.1002/ejoc.200400627>
  • Demange Raynald, Awad Loay, Vogel Pierre: Synthesis of C-linked analogues of β-d-galactopyranosyl-(1→3)-d-galactopyranosides and of β-d-galactopyranosyl-(1→3)-d-galactal. Tet Asymm 2004, 15, 3573. <http://dx.doi.org/10.1016/j.tetasy.2004.09.029>
  • Dondoni Alessandro, Massi Alessandro, Sabbatini Simona, Bertolasi Valerio: Synthesis of C-glycosyl β-amino acids by asymmetric Mannich-type three-component reactions. Tetrahetron Lett 2004, 45, 2381. <http://dx.doi.org/10.1016/j.tetlet.2004.01.070>
  • Alcaide Benito, Almendros Pedro, Redondo María C.: Novel N1−C4 β-Lactam Bond Breakage. Synthesis of Enantiopure α-Alkoxy-γ-keto Acid Derivatives. Org Lett 2004, 6, 1765. <http://dx.doi.org/10.1021/ol049549j>
  • Dondoni Alessandro, Massi Alessandro, Sabbatini Simona: Towards the synthesis of C-glycosylated dihydropyrimidine libraries via the three-component Biginelli reaction. A novel approach to artificial nucleosides. Tetrahetron Lett 2001, 42, 4495. <http://dx.doi.org/10.1016/S0040-4039(01)00769-9>
  • Turner John J., Filippov Dmitri V., Overhand Mark, van der Marel Gijs A., van Boom Jacques H.: Synthesis of novel amino acid carbohydrate hybrids via Mitsunobu glycosylation of nitrobenzenesulfonamides. Tetrahetron Lett 2001, 42, 5763. <http://dx.doi.org/10.1016/S0040-4039(01)01062-0>