LEADER 05400nam 22007091 450 001 9911019275403321 005 20210604103758.0 010 $a9783527658961 010 $a3527658963 010 $a9783527658947 010 $a3527658947 010 $a9783527658978 010 $a3527658971 035 $a(CKB)2550000001172033 035 $a(EBL)1420234 035 $a(SSID)ssj0001164124 035 $a(PQKBManifestationID)11677893 035 $a(PQKBTitleCode)TC0001164124 035 $a(PQKBWorkID)11180729 035 $a(PQKB)11672917 035 $a(MiAaPQ)EBC1420234 035 $a(OCoLC)862948294 035 $a(PPN)219783306 035 $a(Perlego)1003350 035 $a(EXLCZ)992550000001172033 100 $a20131113h20142014 uy 0 101 0 $aeng 135 $aur|n|---||||| 181 $ctxt 182 $cc 183 $acr 200 00$aModern synthetic methods in carbohydrate chemistry $efrom monosaccharides to complex glycoconjugates /$fedited by Daniel B. Werz, Se?bastien Vidal 210 1$aWeinheim :$cWiley-VCH,$d[2014] 210 4$d©2014 215 $a1 online resource (407 p.) 300 $aDescription based upon print version of record. 311 08$a9783527332847 311 08$a3527332847 311 08$a9781306220873 311 08$a1306220874 320 $aIncludes bibliographical references and index. 327 $aCover; Title Page; Copyright; Contents; Foreword; Preface; List of Contributors; 1 De Novo Approaches to Monosaccharides and Complex Glycans; 1.1 Introduction; 1.2 De Novo Synthesis of Monosaccharides; 1.3 Iterative Pd-Catalyzed Glycosylation and Bidirectional Postglycosylation; 1.3.1 Bidirectional Iterative Pd-Catalyzed Glycosylation and Postglycosylation; 1.3.2 Synthesis of Monosaccharide Aminosugar Library; 1.4 Synthesis of Monosaccharide Azasugar; 1.5 Oligosaccharide Synthesis for Medicinal Chemistry; 1.5.1 Tri- and Tetrasaccharide Library Syntheses of Natural Product 327 $a1.5.2 Anthrax Tetrasaccharide Synthesis1.6 Conclusion and Outlook; 1.7 Experimental Section; List of Abbreviations; Acknowledgments; References; 2 Synthetic Methodologies toward Aldoheptoses and Their Applications to the Synthesis of Biochemical Probes and LPS Fragments; 2.1 Introduction; 2.2 Methods to Construct the Heptose Skeleton; 2.2.1 Olefination of Dialdoses Followed by Dihydroxylation; 2.2.1.1 Olefination at C-5 Position of Pentodialdoses; 2.2.1.2 Olefination at C-1 Position of Hexoses; 2.2.1.3 Olefination at C-6 Position of Hexodialdoses; 2.2.2 Homologation by Nucleophilic Additions 327 $a2.2.2.1 Elongation at C-6 of Hexoses2.2.2.2 Elongation at C-1 Position of Aldose; 2.2.3 Heptose de novo synthesis; 2.3 Synthesis of Heptosylated Oligosaccharides; 2.3.1 Synthesis of the Core Tetrasaccharide of Neisseria meningitidis Lipopolysaccharide; 2.3.2 Synthesis of a Branched Heptose- and Kdo-Containing Common Tetrasaccharide Core Structure of Haemophilus influenzae; 2.3.3 Synthesis of the Core Tetrasaccharide of Neisseria gonorrhoeae Lipopolysaccharide 327 $a2.3.4 The Crich's Stereoselective ?-Glycosylation Applied to the Synthesis of the Repeating Unit of the Lipopolysaccharide from Plesimonas shigelloides2.3.5 De Novo Approach Applied to the Synthesis of a Bisheptosylated Tetrasaccharide; 2.4 Synthesis of Heptosides as Biochemical Probes; 2.4.1 Bacterial Heptose Biosynthetic Pathways; 2.4.2 Artificial D-Heptosides as Inhibitors of HldE and GmhA; 2.4.3 Inhibition Studies of Heptosyltransferase WaaC; 2.5 Conclusions; 2.6 Experimental Part; 2.6.1 Typical Synthesis of a D-glycero-Heptoside by Dihydroxylation of a C6-C7 Alkene 327 $a2.6.1.1 Phenyl 1-deoxy-2,3,4-tri-O-benzyl-1-thio-D-glycero-?-D-mannoheptopyranoside (167)2.6.2 Typical Synthesis of a L-glycero-Heptoside by Addition of Grignard Reagent Followed by a Tamao-Fleming Oxidation; 2.6.2.1 Methyl 2,3,4-tri-O-benzyl-7-(phenyldimethyl)silane-7-deoxy-L-glycero-?-D-manno-heptopyranoside (170); 2.6.2.2 Methyl 2,3,4-tri-O-benzyl-L-glycero-?-D-manno-heptopyranoside (171); List of Abbreviations; Acknowledgments; References; 3 Protecting-Group-Free Glycoconjugate Synthesis: Hydrazide and Oxyamine Derivatives in N-Glycoside Formation; 3.1 Introduction 327 $a3.2 Glycosyl Hydrazides (1-(Glycosyl)-2-acylhydrazines) 330 $aThe fields of glycochemistry and glycoscience are rich and varied and where much can be learned from Nature. As Nature is not always able to produce carbohydrates in quantities useful for not only in research but also as therapeutic agents, new ways need to be found to optimize the yield. This book presents an overview of the latest developments in the field of carbohydrates, ranging from de-novo approaches via cyclodextrin chemistry to the synthesis of such highly complex glycoconjugates as glycosphingolipids and GPI anchors. 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