Volumes in the Proven Synthetic Methods Series address the concerns many chemists have regarding irreproducibility of synthetic protocols, lack of identification and characterization data for new compounds, and inflated yields reported in chemical communications—trends that have recently become a serious problem.
Featuring contributions from world-renowned experts and overseen by a highly respected series editor, Carbohydrate Chemistry: Proven Synthetic Methods, Volume 4 compiles reliable synthetic methods and protocols for the preparation of intermediates for carbohydrate synthesis or other uses in the glycosciences.
Exploring carbohydrate chemistry from both the academic and industrial points of view, this unique resource brings together useful information into one convenient reference. The series is unique among other synthetic literature in the carbohydrate field in that, to ensure reproducibility, an independent checker has verified the experimental parts involved by repeating the protocols or using the methods.
The book includes new or more detailed versions of previously published protocols as well as those published in not readily available journals. The essential characteristics of the protocols presented are reliability, updated characterization data for newly synthesized substances and the expectation of wide utility in the carbohydrate field. The protocols presented will be of wide use to a broad range of readers in the carbohydrate field and the life sciences, including undergraduates taking carbohydrate workshops.
Edited by:
Christian Vogel,
Paul Murphy
Imprint: CRC Press Inc
Country of Publication: United States
Dimensions:
Height: 234mm,
Width: 156mm,
Weight: 703g
ISBN: 9781498726917
ISBN 10: 1498726917
Series: Carbohydrate Chemistry: Proven Synthetic Methods
Pages: 369
Publication Date: 19 September 2017
Audience:
College/higher education
,
College/higher education
,
A / AS level
,
Further / Higher Education
Format: Hardback
Publisher's Status: Active
Foreword Introduction Editors Series Editor Contributors Section I Synthetic Methods Chapter 1 Picoloyl-Protecting Group in Oligosaccharide Synthesis: Installation, H-Bond-Mediated Aglycone Delivery (HAD), and Selective Removal Michael P. Mannino, Jagodige P. Yasomanee, Alexei V. Demchenko, and Venukumar Patteti Chapter 2 Monomethoxytrityl (MMTr) as an Efficient S-Protecting Group in the Manipulation of Glycosyl Thiols Raymond Smith, Xiangming Zhu, and Elena Calatrava-Pérez Chapter 3 One-Step Inversion of Configuration of a Hydroxy Group in Carbohydrates Shino Manabe and Markus Blaukopf Chapter 4 Formation and Cleavage of Benzylidene Acetals Catalyzed by NaHSO4∙SiO2 Lifeng Sun, Xin-Shan Ye, and Xingdi Wang Chapter 5 Thiodisaccharides by Photoinduced Hydrothiolation of 2-Acetoxy Glycals Dániel Eszenyi, László Lázár, Anikó Borbás, and Ruairi O. McCourt Chapter 6 One-Step Preparation of Protected N-tert-Butanesulfinyl d-ribo and d-xylo Furanosylamines from Related Sugar Hemiacetals Chloé Cocaud, Cyril Nicolas, Olivier R. Martin, and Jérôme Désiré Chapter 7 An Alternative Preparation of Azides from Amines via Diazotransfer with Triflyl Azide Yuqian Ye, Xin-Shan Ye, and Xingdi Wang Chapter 8 Simple Preparation of Dimethyldioxirane and Its Use as an Epoxidation Agent for the Transformation of Glycals to Glycosyl Phosphates Katharina Kettelhoit, Daniel B. Werz, Aniruddha Sasmal, Xinyu Liu, and Philipp Gritsch Chapter 9 Preparation of Glycosyl Bromides of α-d-Gluco-hept-2-ulopyranosonic Acid Derivatives Veronika Nagy, Katalin Czifrák, László Juhász, László Somsák, and Olena Apelt Chapter 10 Preparation of 2,6-Anhydro-hept-2-enonic Acid Derivatives and Their 3-Deoxy Counterparts Sándor Kun, Szabina Deák, Katalin Czifrák, László Juhász, László Somsák, and Olena Apelt Section II Synthetic Intermediates Chapter 11 Synthesis of 4-Nitrophenyl β-d-galactofuranoside: A Useful Substrate for β-d-Galactofuranosidases Studies Carla Marino, Santiago Poklepovich Caridea, Rosa M. de Lederkremer, and Sydney Villaume Chapter 12 Synthesis of Benzoylated β-d-Glucosamine Derivatives Claudia Di Salvo, Karen A. Fox, Paul V. Murphy, and Jens Langhanki Chapter 13 Synthesis of 3,4,6-Tri-O-benzyl-2-deoxy-2-(p-toluenesulfonamido)-α-d-glucopyranose Vimal K. Harit, Namakkal G. Ramesh, and Srinivasa-Gopalan Sampathkumar Chapter 14 A Convenient Synthesis of 3,4-Di-O-acetyl-d-rhamnal (3,4-Di-O-acetyl-6-deoxy-d-glucal) Jessica N. Spradlin, Dina Lloyd, Clay S. Bennett, and Chao Liang Chapter 15 One-Pot Synthesis of 2-Acetamido-1,3,4,6-tetra-O-acetyl-2-deoxy-β-d-glucopyranose Using Anomeric O-Acylation Sergey S. Pertel, Elena S. Kakayan, Sergey A. Seryi, and Anthony W. McDonagh Chapter 16 1,2,3,5,6-Penta-O-tert-butyl(dimethyl)silyl-β-d-galactofuranose: A Versatile Glycosylating Agent for Galactofuranosylation Diego González-Salas, Carla Marino, and Mónica Guberman Chapter 17 Per-O-benzoyl-1,2-O-benzylidene derivatives of Pyranoses and Furanoses—Versatile Building Blocks for Oligosaccharide Synthesis Polina I. Abronina, Alexander I. Zinin, Nikita M. Podvalnyy, Leonid O. Kononov, and Sandip Pasari Chapter 18 Synthesis of 1,3,4,6-Tetra-O-acetyl-2-azido-2-deoxy-α,β-dglucopyranose Using the Diazo-Transfer Reagent Imidazole-1-sulfonyl Azide Hydrogen Sulfate Garrett T. Potter, Gordon C. Jayson, John M. Gardiner, Lorenzo Guazelli, and Gavin J. Miller Chapter 19 Synthesis of Methyl 2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-α-and β-d-glucopyranosides Alexander S. Henderson, M. Carmen Galan, and Carlo Pifferi Chapter 20 Ring-Opening of Benzylated Gluconolactone to Access Useful Gluconamide Conjugates Sarah Roy, Vincent Denavit, Tze Chieh Shiao, and Denis Giguère Chapter 21 A Multigram Synthesis of Phenyl 2-azido-3-O-benzyl-4,6-Obenzylidene-2-deoxy-1-thio-α-d-mannopyranoside Ivan A. Gagarinov, Apoorva D. Srivastava, Geert-Jan Boons, and Zhen Wang Chapter 22 Preparation and Characterization of 6-Azidohexyl 2,3,4,6-tetra-O-acetyl-β-d-glucopyranoside Divya Kushwaha, Pavol Kováč, and Marek Baráth Chapter 23 Synthesis of (2S, 3S, 4S)-2,3,4-Tri-O-benzyl-5-bromopentanenitrile Michał Malik, Sławomir Jarosz, and Anna Zawisza Chapter 24 Simplifying Access to 3,4-Di-O-acetyl-1,5 anhydro-2,6-dideoxy-d-lyxo-hex-1-enitol (3,4-Di-O-acetyl-d-fucal) Ivan A. Gagarinov, Apoorva D. Srivastava, Geert-Jan Boons, and Satsawat Visansirikul Chapter 25 2-Chloroethyl and 2-Azidoethyl 2,3,4,6-tetra-O-acetyl-β-dgluco-and β-d-galactopyranosides Andrew Reddy, Jessica Ramos-Ondono, Lorna Abbey, Trinidad Velasco-Torrijos, and Thomas Ziegler Chapter 26 Synthesis of Heptakis(6-O-tert-butyldimethylsilyl) cyclomaltoheptaose Juan M. Casas-Solvas, Antonio Vargas-Berenguel, and Milo Malanga Chapter 27 Sodium d-galactonate, d-Galactono-1,4-lactone, and Synthetically Useful Methyl d-galactonates Verónica Rivas, Adriana A. Kolender, Oscar Varela, and Gilbert Duhirwe Chapter 28 Synthesis of a 3,6-Orthogonally-Protected Mannopyranoside Building Block Sarah Roy, Vincent Denavit, Danny Lainé, Denis Giguère, and Julia Meyer Chapter 29 Methyl 3,4,6-tri-O-acetyl-2-deoxy-2-[(bis-methoxycarbonyl) methyl]-β-d-glucopyranoside Prashant Pavashe, Tukaram Pimpalpalle, Torsten Linker, and László Juhász Chapter 30 Fluorine-Containing Carbohydrates: Synthesis of 6-Deoxy-6-fluoro-1,2:3,4-di-O-isopropylidene-α-d-galactopyranose Vincent Denavit, Danny Lainé, Denis Giguère, and Guillaume Le Heiget Chapter 31 A Facile Synthesis of 1,3,4,6-Tetra-O-acetyl-2-deoxy-2-trifluoroacetamido-β-d-glucopyranose Nikita M. Podvalnyy, Yakov V. Voznyi, Alexander I. Zinin, Polina I. Abronina, Leonid O. Kononov, and Salvatore G. Pistorio Chapter 32 An Expeditious Route to an HO-4 Free d-GalNAc Building Block from d-GlcNAc Francisco Santoyo-Gonzalez, Fernando Hernandez-Mateo, F. J. Lopez-Jaramillo, and Clara Uriel Chapter 33 Improved Synthesis of 3-(2-Deoxy-β-d-erythro-pentofuranos-1-yl) prop-1-ene Heike Wächtler, Dilver Peña Fuentes, Olena Apelt, Christian Vogel, Dirk Michalik, and Mykhaylo A. Potopnyk Chapter 34 Improved Synthesis of 3-(β-d-Ribofuranos-1-yl) prop-1-ene Heike Wächtler, Dilver Peña Fuentes, Olena Apelt, Christian Vogel, Dirk Michalik, and Mykhaylo A. Potopnyk Chapter 35 3-Azidopropyl 2-Acetamido-2-deoxy-α-d-glucopyranoside Jean-Baptiste Farcet, Anna Christler, Paul Kosma, and Mihály Herczeg Chapter 36 Large-Scale Synthesis of 2,3,4,6-Tetra-O-benzyl-1-deoxynojirimycin Damien Hazelard, Mathieu L. Lepage, Jérémy P. Schneider, Maëva M. Pichon, Philippe Compain, and Fabien Massicot Chapter 37 Synthesis of Indol-3-yl Glucuronides for Monitoring Glucuronidase Activity Stephan Böttcher, Christian Czaschke, Joachim Thiem, and Mauro Pascolutti Chapter 38 Preparation of 2,6-Anhydro-3,4,5,7-tetra-O-benzyl-d-glycero-dgulo-heptonimidamide Eszter Szennyes, Éva Bokor, Attila Kiss, László Somsák, and Yoann Pascal Chapter 39 Allyl 4,6-O-benzylidene-2-deoxy-2-trichloroacetamido-β-dglucopyranoside Yann Le Guen, Pierre Chassagne, Guillaume Le Heiget, Dominique Urban, and Laurence A. Mulard Chapter 40 1,2-Bis (diphenylphosphano) Ethane (DPPE)-Mediated Synthesis of Glycosyl Amides David P. Temelkoff, Peter Norris, and Adele Gabba Index
Christian Vogel earned a PhD in organic chemistry–heterocyclic chemistry under the supervision of Professor Klaus Peseke at the University of Rostock in 1980. Since 1992, he has served as a professor in the Department of Organic Chemistry, University of Rostock. In addition to fucose chemistry, Dr. Vogel’s main interests are pectin fragment synthesis using the modular design principle, the synthesis of rare sugars for structural investigations, and C-nucleosides. Paul V. Murphy was appointed to the position of Established Professor of Chemistry at National University of Ireland Galway (NUI Galway) in 2008. He is from the West of Ireland (Turloughmore, Co. Galway). His group is engaged in the design and synthesis of bioactive compounds, with a focus on carbohydrates, maintaining a long tradition in carbohydrate research in Galway’s School of Chemistry.
Reviews for Carbohydrate Chemistry: Proven Synthetic Methods, Volume 4
'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.
