LEADER 05441nam 2200661Ia 450 001 9910145681903321 005 20170815112830.0 010 $a1-281-31026-3 010 $a9786611310264 010 $a0-470-76032-X 010 $a0-470-76005-2 035 $a(CKB)1000000000415574 035 $a(EBL)351324 035 $a(OCoLC)437218594 035 $a(SSID)ssj0000216113 035 $a(PQKBManifestationID)11175824 035 $a(PQKBTitleCode)TC0000216113 035 $a(PQKBWorkID)10194866 035 $a(PQKB)10751740 035 $a(MiAaPQ)EBC351324 035 $a(PPN)140516689 035 $a(EXLCZ)991000000000415574 100 $a20000410d2000 uy 0 101 0 $aeng 135 $aur|n|---||||| 181 $ctxt 182 $cc 183 $acr 200 10$aOrganic synthesis with carbohydrates$b[electronic resource] /$fGeert-Jan Boons, Karl J. Hale 210 $aSheffield, England $cSheffield Academic Press ;$aMalden, MA U.S.A. $cBlackwell Science$d2000 215 $a1 online resource (351 p.) 225 1 $aPostgraduate chemistry series 300 $aDescription based upon print version of record. 311 $a1-85075-913-8 320 $aIncludes bibliographical references and index. 327 $aOrganic Synthesis with Carbohydrates; Contents; PART A: STRUCTURE AND SYNTHESIS OF SACCHARIDES AND GLYCOPROTEINS; 1 Mono- and oligosaccharides: structure, configuration and conformation; 1.1 Introduction; 1.2 Configuration of monosaccharides; 1.3 Conformationalpropelties of monosaccharides; 1.3.1 Ring shapes of pyranoses and furanoses; 1.3.2 The anomeric effect; 1.3.3 The equilibrium composition of monosaccharides in solution; 1.4 Conformational properties of oligosaccharides; 1.5 Acid-catalysed glycoside bond formation and cleavage; References; 2 Protecting groups; 2.1 Introduction 327 $a2.2 Ether protecting groups2.2.1 Benzyl ethers; 2.2.2 p-Methoxybenzyl ethers; 2.2.3 Allyl ethers; 2.2.4 Triphenylmethyl ethers; 2.2.5 Silyl ethers; 2.3 Acetal protecting groups; 2.3.1 Benzylidene acetals; 2.3.2 Isopropylidene acetals; 2.3.3 Dispirodiketal and cyclohexane- 1,2-diacetal groups; 2.4 Ester protecting groups; 2.5 Anomeric protecting groups; 2.6 Amino protecting groups; 2.6.1 Phthalimides; 2.6.2 Azides; References; 3 Functionalised saccharides; 3.1 General introduction; 3.2 Deoxyhalogeno sugars; 3.2.1 Introduction; 3.2.2 Direct halogenation of alcohols; 3.2.3 Displacement reactions 327 $a3.2.4 Miscellaneous methods3.3 Unsaturated sugar derivatives; 3.3.1 Introduction; 3.3.2 Glycals; 3.3.3 lsolated double bonds; 3.3.4 6-Deoxy-hex-5-enopyranose derivatives; 3.4 Deoxy sugars; 3.4.1 Introduction; 3.4.2 Reduction of halides, sulfonates and epoxides; 3.4.3 Radical deoxygenation of thiocarbonyl derivatives; 3.5 Amino sugars; 3.5.1 lntroduction; 3.5.2 The preparation of amino sugars by nucleophilic displacement; 3.5.3 Addition to glycals; 3.5.4 Reduction of oximes; 3.5.5 Intramolecular substitutions; 3.6 Epoxy sugars; 3.7 Sulfated saccharides; 3.7.1 lntroduction 327 $a3.7.2 0 and N sulfation3.8 Phosphorylated saccharides; 3.8.1 lntroduction; 3.8.2 Non-anomeric sugar phosphates; 3.8.3 Anomeric phosphates; References; 4 Oligosaccharide synthesis; 4.1 Introduction; 4.2 Chemical glycosidic bond synthesis; 4.2.1 Glycosyl halides; 4.2.2 Trichloroacetimidates; 4.2.3 Thioglycosides; 4.3 Stereoselective control in glycosidic bond synthesis; 4.3.1 Neighbouring-group-assisted procedures; 4.3.2 In situ anomerisation; 4.3.3 Glycosylation with inversion of configuration; 4.3.4 Solvent participation; 4.3.5 Intramolecular aglycon delivery 327 $a4.4 Preparation of 2-amino-2-deoxy-glycosides4.5 Formation of glycosides of N-acetyl-neuraminic acid; 4.6 The introduction of 2-deoxy glycosidic linkages; 4.7 Convergent block synthesis of complex oligosaccharides; 4.8 Chemoselective glycosylations and one-pot multistep glycosylations; 4.9 Solid-phase oligosaccharide synthesis; 4.10 Enzymatic glycosylation strategies; 4.10.1 Glycosyl transferases; 4.10.2 Glycosyl hydrolases; References; 5 The chemistry of 0- and N-linked glycopeptides; 5.1 Introduction; 5.2 Strategies for the chemical synthesis of glycopeptides 327 $a5.3 Protecting groups in glycopeptide synthesis 330 $aCarbohydrates offer a ready source of enantiomerically pure starting materials. They have been used for the imaginative synthesis of a wide range of compounds, and have been found to be effective chiral auxiliaries which enable the introduction of a range of functionalities in a highly enantioselective manner. In a subject dominated by volumes at research and professional level, this book provides a broad understanding of the use of carbohydrates in organic synthesis, at postgraduate student level. Emphasis is placed on retrosynthetic analysis, with discussion of why a particular synthet 410 0$aPostgraduate chemistry series. 606 $aCarbohydrates$xSynthesis 606 $aOrganic compounds$xSynthesis 615 0$aCarbohydrates$xSynthesis. 615 0$aOrganic compounds$xSynthesis. 676 $a547.2 676 $a547/.780459 700 $aBoons$b Geert-Jan$0877768 701 $aHale$b Karl$0888208 801 0$bMiAaPQ 801 1$bMiAaPQ 801 2$bMiAaPQ 906 $aBOOK 912 $a9910145681903321 996 $aOrganic synthesis with carbohydrates$91984077 997 $aUNINA