LEADER 05245nam 2200625 450 001 9910830452103321 005 20170809161016.0 010 $a1-282-78437-4 010 $a9786612784378 010 $a3-527-62164-4 010 $a3-527-62165-2 035 $a(CKB)1000000000687244 035 $a(EBL)481958 035 $a(OCoLC)609855488 035 $a(SSID)ssj0000354276 035 $a(PQKBManifestationID)11277474 035 $a(PQKBTitleCode)TC0000354276 035 $a(PQKBWorkID)10302364 035 $a(PQKB)10619820 035 $a(MiAaPQ)EBC481958 035 $a(PPN)194593797 035 $a(EXLCZ)991000000000687244 100 $a20160820h20082008 uy 0 101 0 $aeng 135 $aur|n|---||||| 181 $ctxt 182 $cc 183 $acr 200 00$aHandbook of chemical glycosylation $eadvances in stereoselectivity and therapeutic relevance /$fedited by Alexei V. Demchenko 210 1$aWeinheim, [Germany] :$cWiley-VCH Verlag GmbH & Co. KGaA,$d2008. 210 4$dİ2008 215 $a1 online resource (525 p.) 300 $aDescription based upon print version of record. 311 $a3-527-31780-5 320 $aIncludes bibliographical references at the end of each chapters and index. 327 $aHandbook of Chemical Glycosylation; Contents; Preface; List of Contributors; 1 General Aspects of the Glycosidic Bond Formation; 1.1 Introduction; 1.2 Major Types of O-Glycosidic Linkages; 1.3 Historical Development: Classes of Glycosyl Donors; 1.4 General Reaction Mechanism; 1.5 Anomeric Effects; 1.6 Stereoselectivity of Glycosylation; 1.6.1 Structure of the Glycosyl Donor; 1.6.1.1 Protecting Groups; 1.6.1.2 Leaving Group; 1.6.2 Structure of the Glycosyl Acceptor; 1.6.2.1 Position of the Hydroxyl; 1.6.2.2 Protecting Groups; 1.6.3 Reaction Conditions; 1.6.3.1 Solvent Effect 327 $a1.6.3.2 Promoter (Catalyst), Additions1.6.3.3 Temperature and Pressure; 1.6.4 Other Factors; 1.7 Special Cases of Glycosylation; 1.7.1 Aminosugars; 1.7.2 Sialosides; 1.7.3 Synthesis of 2-Deoxyglycosides; 1.7.4 Synthesis of ?-Mannosides; 1.7.5 Synthesis of Furanosides; 1.8 Glycosylation and Oligosaccharide Sequencing; 1.8.1 Leaving-Group-Based Strategies; 1.8.2 Two-Step Activation and Preactivation Strategies; 1.8.3 Protecting-Group-Based Strategies; 1.9 Conclusions and Outlook; References; 2 Glycoside Synthesis from Anomeric Halides; 2.1 Glycosyl Fluorides; 2.1.1 Background 327 $a2.1.2 Synthesis of Glycosyl Fluoride Donors2.1.2.1 Fluorinating Reagents; 2.1.2.2 Glycosyl Fluorides from Hemiacetals; 2.1.2.3 Glycosyl Fluorides from Glycosyl Esters; 2.1.2.4 Glycosyl from Glycosyl Halides; 2.1.2.5 Glycosyl Fluorides from S-Glycosides; 2.1.2.6 Glycosyl Fluorides from Other Anomeric Moieties; 2.1.3 Glycosylation Using Glycosyl Fluorides as Glycosyl Donors; 2.1.3.1 A Weak Lewis Acid Cleaves the C-F Bond. How Was the Glycosyl Fluoride Method Discovered?; 2.1.3.2 Various Promoters Employed in Glycosylation by the Glycosyl Fluoride Method 327 $a2.1.3.3 Glycosylations Promoted by Various Promoters2.1.3.4 Glycosylation of Silylated Compounds as Glycosyl Acceptors; 2.1.3.5 Two-Stage Activation Procedure; 2.1.3.6 Protecting-Group-Based Strategy; 2.1.4 Application to Natural Product Synthesis; 2.1.5 Special Topics; 2.1.5.1 C-Glycoside Synthesis via O-Glycosylation; 2.1.5.2 Glycosyl Fluorides for the Synthesis of a Combinatorial Library; 2.1.5.3 Glycosyl Fluorides as Glycosyl Donors for Chemoenzymatic Synthesis; 2.1.6 Conclusions and Future Directions; 2.1.7 Typical Experimental Procedures; 2.1.7.1 Preparation of the Glycosyl Donors 327 $a2.1.7.2 Glycosylation Using Glycosyl Fluorides as Glycosyl DonorsReferences; 2.2 Glycosyl Chlorides, Bromides and Iodides; 2.2.1 Background; 2.2.2 Glycosyl Chlorides; 2.2.2.1 Preparation of Glycosyl Chlorides; 2.2.2.2 Reactions of Glycosyl Chlorides; 2.2.3 Glycosyl Bromides; 2.2.3.1 Preparation of Glycosyl Bromides; 2.2.3.2 Reactivity Patterns and Some Useful Reactions of Glycosyl Bromides; 2.2.3.3 Stereoselective Glycosylations Employing Glycosyl Bromides and Applications; 2.2.4 Glycosyl Iodides; 2.2.4.1 Preparation of Glycosyl Iodides; 2.2.4.2 Reactions of Glycosyl Iodides 327 $a2.2.5 Conclusions 330 $aSince carbohydrate oligomers are still a challenge in synthetic chemistry, this book on recent developments fulfils a great need. Covering the chemistry necessary to synthesize exact copies of these structures, top authors from all around the world comprehensively deal with synthesis from anomeric halides, from miscellaneous glycosyl donors, and by indirect and special methods, as well as 1-oxygen-and 1-sulfur-substituted derivatives. They demonstrate the best approach for the stereoselective formation of the intermonomeric bond, making this essential reading for every biochemist working in bi 606 $aGlycosylation 606 $aOligomers 615 0$aGlycosylation. 615 0$aOligomers. 676 $a547.78 702 $aDemchenko$b Alexei V. 801 0$bMiAaPQ 801 1$bMiAaPQ 801 2$bMiAaPQ 906 $aBOOK 912 $a9910830452103321 996 $aHandbook of chemical glycosylation$93954593 997 $aUNINA