Carbohydrate Chemistry: Proven Synthetic Methods, Volume 1 by Pavol Ková¿Carbohydrate Chemistry: Proven Synthetic Methods, Volume 1 by Pavol Ková¿

Carbohydrate Chemistry: Proven Synthetic Methods, Volume 1

EditorPavol Ková¿, Pavol Kováä

Hardcover | September 22, 2011

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Long gone are the days when synthetic publications included parallel preparative experiments to document reproducibility of the experimental protocols and when journals required such documentation. The newProven Synthetic Methods Seriesaddresses concerns to chemists regarding irreproducibility of synthetic protocols, lack of characterization data for new compounds, and inflated yields reported in many chemical communications¿trends that have recently become a serious problem.

Volume One of Carbohydrate Chemistry: Proven Synthetic Methodsincludes more detailed versions of protocols previously published for the synthesis of oligosaccharides, C-glycosyl compounds, sugar nucleotides, click chemistry, thioglycosides, and thioimidates, among others. The compilation of protocols covers both common and less frequently used synthetic methods as well as examples of syntheses of selected carbohydrate intermediates with general utility. The major focus of this book is devoted to the proper practice of state-of-the-art preparative procedures, including:

  • References to the starting materials used, reaction setup, work-up and isolation of products, followed by identification and proof of purity of the final material
  • General information regarding convenience of operation and comments on safety issues
  • Versatile and practically useful methods that have not received deserved, long-lasting recognition or that are difficult to access from their primary sources
  • Copies of 1D NMR spectra of compounds prepared, showing purity of materials readers can expect

Exploring carbohydrate chemistry from the academic points of view, theCarbohydrate Chemistry: Proven Synthetic MethodsSeriesprovides a compendium of preparatively useful procedures checked by chemists from independent research groups.

Series editorPavol Kov¿/STRONG>, Ph.D., Dr. h.c., with more than 40 years of experience in carbohydrate chemistry and more than 270 papers published in refereed scientific journals or books, is a strong promoter of good laboratory practices and a vocal critic of the publication of experimental chemistry lacking data that allows reprodu...
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Title:Carbohydrate Chemistry: Proven Synthetic Methods, Volume 1Format:HardcoverDimensions:468 pages, 9.25 × 6.14 × 0.98 inPublished:September 22, 2011Publisher:Taylor and FrancisLanguage:English

The following ISBNs are associated with this title:

ISBN - 10:1439866899

ISBN - 13:9781439866894

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Table of Contents

Synthetic Methods
Acetolysis of 6-Deoxysugars Controlled by Armed¿Disarmed Effect
Emiliano Bedini, Luigi Cirillo, Ian Cumpstey, and Michelangelo Parrilli
NaH/Im2SO2-Mediated Preparation of Hex-2- and Hex-3-Enopyranoside Enol Ethers
Emanuele Attolino, Giorgio Catelani, Felicia D. Andrea, Lorenzo Guazzelli, and Marie-Christine Scherrmann
Enhancement of the Rate of Purdie Methylation by Me2S Catalysis
Shujie Hou, Thomas Ziegler, and Pavol Kov¿Synthesis of Oligosaccharides by Preactivation-Based Chemoselective Glycosylation of Thioglycosyl Donors
Zhen Wang, Gilbert Wasonga, Benjamin M. Swarts, and Xuefei Huang
The Use of Hypophosphorous Acid in Radical Chain Deoxygenation of Carbohydrates
Karsten Krohn, Ivan Shuklov, Ishtiaq Ahmed, and Alice Voss
Diphenylsulfoxide-Trifluoromethanesulfonic Anhydride: A Potent Activator for Thioglycosides
Jeroen D.C. Codee, Thomas J. Boltje, and Gijsbert A. van der Marel
Preparation of Glycosyl Chlorides from Glycopyranoses/Glycofuranoses under Mild Conditions
Chih-Wei Chang, Chin-Sheng Chao, Chang-Ching Lin, and Kwok-Kong T. Mong
C
-Glycosylation Starting from UnprotectedO-Glycosides
Barbara La Ferla, Laura Cipolla, Wouter Hogendorf, and Francesco Nicotra
Palladium-Catalyzed Sonogashira Coupling onp-Lodophenyl ¿-D-MannopyranosideTze Chieh Shiao, Jacques Rodrigue, and Mohamed Touaibia
Synthesis by "Click Chemistry" of an ¿-D-Mannopyranoside Having a 1,4-Disubstituted Triazole as Aglycone
Tze Chieh Shiao, Denis Giguere, and Mohamed Touaibia
Synthesis of Methyl Glycuronates by Chemo- and Regioselective TEMPO/BAIB-Oxidation
Marthe T.C. Walvoort, Deepak Sail, Gijsbert A. van der Marel, and Jeroen D.C. Cod¿BR>Synthesis of Sugar Nucleotides: A Phosphoramidite Approach
Henrik Gold, Karine Descroix, Jeroen D.C. Cod¿ and Gijsbert A. van der Marel
Conversion ofN-2,2,2-Trichloroethoxycarbonyl-Protected 2-Aminoglycosides intoN-Alkylated 2,3-N,O-Carbonyl Glycosides
Thomas Honer, Siegfried F¿rster, and Thomas Ziegler
TIBAL-Induced Rearrangement: Synthesis ofgem-Difluorocarbagalactose
Jo¿Sardinha, Am¿a Pilar Rauter, Matthieu Sollogoub, and Yves Bleriot
Pyranose-Fused Butenolides: An Expedient Preparation from Furanose Synthons
Nuno M. Xavier, Sebastian Kopitzki, and Am¿a Pilar Rauter
Glycal Dimerization with High Diastereoselectivity
Andreas H. Franz, Paul H. Gross, and Katja Michael
Regioselective Debenzylation ofC-Glycosylpropene
Laura Cipolla, Barbara La Ferla, Am¿a Pilar Rauter, and Francesco Nicotra
Synthesis of Azido-Functionalized Carbohydrates for the Design of Glycoconjugates
Samy Cecioni, Mehdi Almant, Jean-Pierre Praly, and S¿stien Vidal
Synthesis of Thioglycosides and Thioimidates from Glycosyl Halides
Archana R. Parameswar, Daniel Mueller, Lin Liu, Cristina De Meo, and Alexei V. Demchenko
Synthesis of Thioglycosides and Thioimidates from Peracetates
Archana R. Parameswar, Akihiro Imamura, and Alexei V. Demchenko

Synthetic Intermediates
2-Acetamido-4,6-O-Benzylidene-2-Deoxy-D-Glucopyranose
Sergey S. Pertel, Sergey A. Gunchak, Elena S. Kakayan, Vasily Ya. Chirva, and S¿stien Vidal
Synthesis of 1,3,4,6-Tetra-O-Acetyl-2-Azido-2-Deoxy-¿,¿-D-Glucopyranose and 2-Azido-4,6-O-Benzylidene-2-Deoxy-¿,¿-D-GlucopyranoseRafael Ojeda, Jos¿uis de Paz, Ricardo Lucas, Niels Reichardt, Lin Liu, and Manuel Mart¿Lomas
An Easy Access to 2,3,4,6-Tetra-O-Benzyl-D-Galactopyranose and 2,3,6-Tri-O-Benzyl-D-Glucopyranose
Ian Cumpstey, Riccardo Cribiu, and Lorenzo Guazzelli
Benzyl 2,3,6,2¿,3¿,6¿-Hexa-O-Benzyl-¿-CellobiosideDeepak Sail, Paula Correia da Silva, and Pavol Kov¿One-Step Syntheses of 1,2,3,5,6-Penta-O-Benzoyl-¿,¿-D-Galactofuranose and 1,2,3,5-Tetra-O-Benzoyl-¿,¿-D-ArabinofuranoseCarla Marino, Luc¿Gandolfi-Donad¿ Carola Gallo Rodriguez, Yu Bai, and Rosa M. de Lederkremer
Stereoselective Synthesis of ¿-C-Sialyl Compounds
Jin-Hwan Kim, Fei Huang, Sayaka Masuko, Deepak Sail, and Robert J. Linhardt
Synthesis ofO-AcetylatedN-Acetylneuraminic Acid Glycal
Nadezhda Y. Kulikova, Anna M. Shpirt, Alexander Chinarev, and Leonid O. Kononov
Substituted Benzyl Glycosides ofN-Acetylneuraminic Acid
Alexander Chinarev, A.B. Tuzikov, A.I. Zinin, and N.V. Bovin
Synthesis of 1,5-Di-C-Alkyl 1,5-Iminoxylitols Related to 1-Deoxynojirimycin
Vincent Chagnault, Philippe Compain, Olivier R. Martin, and Jean-Bernard Behr
Synthesis of 1,6-Anhydro-2,3,5-Tri-O-Benzoyl-¿-D-GalactofuranoseSujit K. Sarkar, Ambar K. Choudhury, J¿Hirsch, and Nirmolendu Roy
Synthesis of Prop-2-Ynyl 2,3,4,6-Tetra-O-Acetyl-¿-D-Mannopyranoside
Yoann M. Chabre, Tze Chieh Shiao, S¿stien Vidal, and Ren¿oy
Synthesis of 3-C-(2,3,4,6-Tetra-O-Acetyl-¿-D-Galactopyranosyl)prop-1-EneSubhash Rauthu, Tze Chieh Shiao, Dominique Lafont,and Ren¿oy
Synthesis of (E)-Methyl 4-(2,3,4,6-Tetra-O-Acetyl-¿-D-Galactopyranosyl)but-2-Enoate by Cross-Metathesis ReactionDenis Gigu¿, Jacques Rodrigue, David Goyard, and Ren¿oy
Preparation ofO-¿-D-Galactopyranosylhydroxylamine
Tze Chieh Shiao, Alex Papadopoulos, Olivier Renaudet, and Ren¿oy
Synthesis of 2,3,4,6-Tetra-O-Acetyl-1,5-Anhydro-D-Lyxo-Hex-1-Enitol and Its Conversion into a Hex-3-Enopyranosid-2-Ulose Analogue of Levoglucosenone
Ver¿nica E. Manzano, Evangelina Repetto, Mar¿Laura Uhrig, Marek Bar¿, and Oscar Varela
Efficient Synthesis of Methyl(Allyl 4-O-Acyl-2,3-Di-O-Benzyl-¿-D-Galactopyranosid)uronates from d-Galacturonic Acid
Alice Voss, Navid Nemati, Hmayak Poghosyan, Hans-Ulrich Endress, Andreas Krause, and Christian Vogel
Methyl(Ethyl 2,3,5-Tri-O-Benzoyl-1-Thio-¿,¿-D-Galactofuranosid)uronate
Ambar K. Choudhury, Dirk Michalik, Andreas Gottwald, and Nirmolendu Roy
p
-Tolyl 2,3,5-Tri-O-Benzoyl-1-Thio-¿-D-Arabinofuranoside: A Useful Thioglycoside Building Block in the Synthesis of Oligoarabinofuranosides
Maju Joe, Yu Bai, Luc¿Gandolfi-Donad¿ and Todd L. Lowary
Ethylene Dithioacetals of Common Hexoses
Rui C. Pinto, Marta M. Andrade, C¿le Ouairy, and Maria Teresa Barros
Preparation of 2,6-Anhydro-Aldose Tosylhydrazones
Marietta T¿th, L¿l¿ Soms¿ and David Goyard
Preparation ofExo-Glycals from (C-Glycopyranosyl) formaldehyde Tosylhydrazone
Marietta T¿th, S¿or Kun, L¿l¿ Somsak, and David Goyard
Synthesis ofO-(6-Deoxy-¿- and ¿-l-Galactopyranosyl) Hydroxylamines (¿- and ¿-l-Fucopyranosylhydroxylamines)Isabelle Bossu, Barbara Richichi, Pascal Dumy, and Olivier Renaudet
Functionalization of Terminal Positions of Sucrose¿Part I: Synthesis of 2,3,3¿,4,4¿-Penta-O-Benzylsucrose and Differentiation of the Terminal Positions (1,6,6¿)
Mateusz Mach, A. Zawisza, B. Lewandowski, and S. Jarosz
Functionalization of Terminal Positions of Sucrose¿Part II: Preparation of 1¿,2,3,3¿,4,4¿-Hexa-O-Benzylsucrose and 6,6¿-Bis-O-(2-Hydroxyethyl)-1¿,2,3,3¿,4,4¿-Hexa-O-Benzylsucrose
B. Lewandowski, A. Listkowski, K. Petrova, and S. Jarosz
Index

Editorial Reviews

'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. Cornforth JW. Austr. J. Chem. 1993;46:157e70. 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.