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 Kovac 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 Unprotected
O-Glycosides
Barbara La Ferla, Laura Cipolla, Wouter Hogendorf, and
Francesco Nicotra
Palladium-Catalyzed Sonogashira Coupling
on p-Lodophenyl -D-Mannopyranoside Tze 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. Codee
Synthesis of Sugar Nucleotides: A
Phosphoramidite Approach
Henrik Gold, Karine Descroix, Jeroen D.C. Codee, and Gijsbert
A. van der Marel
Conversion of
N-2,2,2-Trichloroethoxycarbonyl-Protected
2-Aminoglycosides into N-Alkylated
2,3-N,O-Carbonyl Glycosides
Thomas Honer, Siegfried Foerster, and Thomas
Ziegler
TIBAL-Induced Rearrangement: Synthesis of
gem-Difluorocarbagalactose
Joao Sardinha, Amelia Pilar Rauter, Matthieu Sollogoub, and
Yves Bleriot
Pyranose-Fused Butenolides: An Expedient
Preparation from Furanose Synthons
Nuno M. Xavier, Sebastian Kopitzki, and Amelia Pilar
Rauter
Glycal Dimerization with High
Diastereoselectivity
Andreas H. Franz, Paul H. Gross, and Katja
Michael
Regioselective Debenzylation of
C-Glycosylpropene
Laura Cipolla, Barbara La Ferla, Amelia Pilar Rauter, and
Francesco Nicotra
Synthesis of Azido-Functionalized
Carbohydrates for the Design of Glycoconjugates
Samy Cecioni, Mehdi Almant, Jean-Pierre Praly, and Sebastien
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 Sebastien 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-Glucopyranose
Rafael Ojeda, Jose Luis de Paz, Ricardo Lucas, Niels Reichardt,
Lin Liu, and Manuel Martin-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-
-Cellobioside Deepak Sail, Paula Correia da Silva, and Pavol
Kovac One-Step Syntheses of
1,2,3,5,6-Penta-O-Benzoyl- , -D-Galactofuranose and
1,2,3,5-Tetra-O-Benzoyl- , -D-Arabinofuranose Carla
Marino, Lucia Gandolfi-Donadio, 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 of O-Acetylated
N-Acetylneuraminic Acid Glycal
Nadezhda Y. Kulikova, Anna M. Shpirt, Alexander Chinarev, and
Leonid O. Kononov
Substituted Benzyl Glycosides of
N-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-Galactofuranose
Sujit K. Sarkar, Ambar K. Choudhury, Jan Hirsch, and Nirmolendu
Roy
Synthesis of Prop-2-Ynyl
2,3,4,6-Tetra-O-Acetyl- -D-Mannopyranoside
Yoann M. Chabre, Tze Chieh Shiao, Sebastien Vidal, and Rene
Roy
Synthesis of
3-C-(2,3,4,6-Tetra-O-Acetyl-
-D-Galactopyranosyl)prop-1-Ene Subhash Rauthu, Tze Chieh Shiao,
Dominique Lafont,and Rene Roy
Synthesis of
(E)-Methyl 4-(2,3,4,6-Tetra-O-Acetyl-
-D-Galactopyranosyl)but-2-Enoate by Cross-Metathesis Reaction
Denis Giguere, Jacques Rodrigue, David Goyard, and Rene
Roy
Preparation of O-
-D-Galactopyranosylhydroxylamine
Tze Chieh Shiao, Alex Papadopoulos, Olivier Renaudet, and Rene
Roy
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
Veronica E. Manzano, Evangelina Repetto, Maria Laura Uhrig,
Marek Barath, 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, Lucia Gandolfi-Donadio, and Todd L.
Lowary
Ethylene Dithioacetals of Common Hexoses
Rui C. Pinto, Marta M. Andrade, Cecile Ouairy, and Maria Teresa
Barros
Preparation of 2,6-Anhydro-Aldose
Tosylhydrazones
Marietta Toth, Laszlo Somsak, and David
Goyard
Preparation of Exo-Glycals from
(C-Glycopyranosyl) formaldehyde Tosylhydrazone
Marietta Toth, Sandor Kun, Laszlo Somsak, and David
Goyard
Synthesis of O-(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
Series editor Pavol Kovac, 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 reproducibility. He obtained an MSc in Chemistry at Slovak Technical University in Bratislava (Slovakia) and a PhD in Organic Chemistry at the Institute of Chemistry, Slovak Academy of Sciences, Bratislava. After postdoctoral training at the Department of Biochemistry, Purdue University, Lafayette, Indiana (R. L. Whistler, advisor), he returned to the Institute of Chemistry and formed a group of synthetic carbohydrate chemists, active mainly in oligosaccharide chemistry, which put the Institute on the map for quality synthetic carbohydrate chemistry. After relocating to the United States in 1981, he first worked at Bachem, Inc., Torrance, California, where he established a laboratory for production of oligonucleotides for the automated synthesis of DNA. In 1983 he joined the National Institutes of Health, 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, originally established by America's greatest carbohydrate chemist, Claude S. Hudson. Dr. Kovac's main interest is in development of conjugate vaccines for bacterial diseases from synthetic carbohydrate antigens.
'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.
- 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.
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