Description
Book SynopsisThe second volume in the series Carbohydrate Chemistry: Proven Synthetic Methods, Volume 2 offers a collection of synthetic procedures valuable to the practice of synthetic carbohydrate chemistry. The series takes an important and unique approach in that all described procedures have been independently verified as reliable and reproducible. With editors and contributors who are highly respected scientists in the field, this book provides a widely useful reference for both researchers and students, exploring carbohydrate chemistry from both academic and industrial points of view.
The book begins with an introductory section that offers tricks and tips collected by the series editor from many years of experience working in carbohydrate laboratories. The subsequent chapters present detailed protocols on both specific synthetic transformations and the preparation of common synthetic intermediates, with figures to aid in comprehension. Procedures are described for regiosele
Trade Review
'The contributors are the best scientists in the field and the series editor is highly respected. The volumes will ... be of use to undergraduates involved in carbohydrate workshops.'
– Alexei Demchenko, Associate Professor of Chemistry and Biochemistry, Director of Graduate Studies, University of Missouri – St. Louis.
‘This essential book series, focused on carbohydrate synthesis, starts with a dedication to Nobel Laureate Sir John W. Cornforth, who is credited with the first public criticism of what he pictured as ‘pouring a large volume of unpurified sewage into the chemical literature.’1 Unfortunately, this issue is not limited to the field of chemistry as many high profile cases of irreproducible experiments have led to alarms being set off even in the popular press.2 This series then serves as the much-needed water treatment plants – places where the reader can be guaranteed a good clean reproducible experiment. … at least now chemists with or without expertise in carbohydrates can count on finding reliable procedures to make sugar-based compounds at one scale – a major achievement. Not only should current practitioners gain back time lost in attempts to properly reconstruct experimental procedures, but these procedures should also allow more creative scientists to contribute to this growing area.
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- Cornforth JW. Austr. J. Chem. 1993;46:157e70.
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- For example, see Unreliable research: trouble at the lab. Econ. October 19, 2013.’
– Nicola L.B. Pohl, Indiana University, Department of Chemistry, Bloomington, IN, USA, for Carbohydrate Research, http://dx.doi.org/10.1016/j.carres.2015.04.007.
Table of ContentsSection 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.
