Carbohydrate Chemistry

Series Editor:Pavol Kováč, Ph.D., Dr. h.c., obtained his Ph.D. in organic chemistry at the Institute of Chemistry, Slovak Academy of Sciences, Bratislava. Dr. Kováč is a strong promoter of good laboratory practices and a vocal critic of the publication of experimental chemistry lacking data that allow reproducibility. He has more than 40 years of experience in carbohydrate chemistry and over 280 papers published in refereed scientific journals, several patents, and book chapters. He joined the National Institutes of Health (NIH) (Bethesda, Maryland) in 1983 where he is currently one of the principal investigators and chief of the Section on Carbohydrates (NIDDK, Laboratory of Bioorganic Chemistry). The world’s oldest research group continuously working on chemistry, biochemistry, and immunology of carbohydrates, it was originally established by the American carbohydrate chemist Claude S. Hudson. Kováč’s main interest is the development of conjugate vaccines for bacterial diseases from synthetic carbohydrate antigens. Volume Two Editors: Jeroen Codée obtained his Ph.D. from Leiden University, the Netherlands, under the guidance of Jacques van Boom and Stan van Boeckel in 2004. Codée then moved to the Eidgenossische Technische Hochschule (ETH) Zurich, Switzerland, for a two-year post-doctoral stay with Peter Seeberger. He subsequently returned to Leiden University, where he is now an associate professor in bio-organic chemistry. His research focuses on glycochemistry and glycobiology, ranging from fundamental organic synthesis to vaccine/drug development and the development of glycobiology tools. He has authored or co-authored more than 70 publications and seven book chapters. Gijs van der Marel conducted his Ph.D. studies on DNA chemistry with Jacques van Boom and received his Ph.D. degree in 1981 from Leiden University, the Netherlands. He has remained associated with this university, where he is now a full professor in synthetic organic chemistry. He has supervised more than 70 Ph.D. students and authored or co-authored over 700 papers. His research focuses on all synthetic aspects of biopolymers, including nucleic acids, peptides, and carbohydrates, and hybrids and analogues thereof.

Section I: Synthetic Methods. Highly Stereoselective 1,2-cis-Glycosylations Employing C-2 (S)-(Phenylthiomethyl)benzyl Ether as a Chiral Auxiliary. Regioselective Reductive Openings of 4,6-O-Benzylidene-Type Acetals Using LiAlH4-AlCl3. A Facile Method for Oxidation of Primary Alcohols to Carboxylic Acids in Carbohydrate Synthesis. Ultrasonic Energy Promoted Allylation to Generate 1-C-(2,3,4,6-Tetra-O-benzyl-α-d-glucopyranosyl)prop-2-ene. Synthesis of a Multivalent Glycocyclopeptide Using Oxime Ligation. Reductive Amination Methodology for Synthesis of Primary Amines from Unprotected Synthons. General Preparation of Imidazole-1-sulfonate Esters. Regioselective Monoacylation and Monoalkylation of Carbohydrates Catalyzed by a Diarylborinic Ester. The Synthesis of Carbamates from Alkenylamines. Hydrolysis of Thioglycosides Using Anhydrous N-Iodosuccinimide (NIS) and Trifluoroacetic Acid (TFA). Highly Diastereoselective Construction of l-Heptosides by a Sequential Grignard Addition/Fleming-Tamao Oxidation. Synthesis of Fluorinated Exo-glycals Mediated by Selectfluor. A Direct and Stereospecific Approach to the Synthesis of α-Glycosyl Thiols. Efficient Microwave-Assisted Synthesis of 1′,2,3,3′,4,4′,6-Hepta-O-benzyl-sucrose and 1′,2,3,3′,4,4′-Hexa-O-benzylsucrose. Section II: Synthetic Intermediates. Oligosaccharide-Salicylaldehyde Derivatives as Precursors of Water-Soluble, Biocompatible Anion Receptors. Allyl 3,4,6-Tri-O-Benzyl-α-d-Mannopyranoside. Synthesis of a Spacer-Armed 6′-Sialyl-N-Acetyllactosamine. Synthesis of β-(1→3)-mannobiose. Phenyl 4,6-O-Benzylidene-1-thio-α-d-mannopyranoside. Synthesis of 1,3,4,6-Tetra-O-acetyl-α-d-glucopyranose Revisited. Synthesis of 4,6-O-Benzylidene Acetals of Methyl α-d-Glucopyranoside, Ethyl 1-Thio-β-d-gluco- and Galactopyranoside. Synthesis of α-N-Acetylneuraminic Acid Methyl Glycoside. Synthesis of Ammonium 3-Deoxy-d-manno-oct-2-ulopyranosylonate (Ammonium Kdo). Synthesis and Characterization of Tetra-O-propargyl Pentaerythritol. Improved Synthesis of Ethyl (2,3,4,6-Tetra-O-acetyl-β-d-galactopyranosyl)-(1→3)-4,6-O-benzylidene-2-deoxy-1-thio-2-trichloroacetamido-β-d-glucopyranoside. Synthesis of α-d-Galactofuranosyl Phosphate. Synthesis of 1,2 4,5-Di-O-(3,3-pentylidene)arabitol via Kinetic Acetal Formation. 1,2-Anhydro-3,4,6-tri-O-benzyl-β-d-mannopyranose. Synthesis of Glucosyl C-1 Dihalides from Tetra-O-acetyl-β-d-glucopyranosyl Chloride. Synthesis of 3,4,6-Tri-O-acetyl-d-galactal. Efficient Synthesis of Hepta-O-acetyl-β-lactosyl Azide via Phase Transfer Catalysis. Synthesis of 2,3,4,6-Tetra-O-acetyl-α-d-mannopyranosyl Azide. Synthesis of Phenyl 2,3,4,6-Tetra-O-acetyl-1-thio-β-d-galactopyranoside. An Alternative, Large-Scale Synthesis of 1,2 5,6-Di-O-isopropylidene-α-d-ribo-hex-3-ulofuranose.