LEADER 05392nam 2200649Ia 450 001 9910140010803321 005 20190709120929.0 010 $a1-282-33153-1 010 $a9786612331534 010 $a0-470-74904-0 010 $a0-470-74905-9 035 $a(CKB)1000000000807934 035 $a(EBL)547167 035 $a(OCoLC)501316340 035 $a(SSID)ssj0000301811 035 $a(PQKBManifestationID)11247571 035 $a(PQKBTitleCode)TC0000301811 035 $a(PQKBWorkID)10263324 035 $a(PQKB)10227219 035 $a(MiAaPQ)EBC547167 035 $a(EXLCZ)991000000000807934 100 $a20090803d2009 uy 0 101 0 $aeng 135 $aur|n|---||||| 181 $ctxt 182 $cc 183 $acr 200 00$aLinker strategies in solid-phase organic synthesis$b[electronic resource] /$fedited by Peter J. H Scott 210 $aHoboken, NJ $cWiley$d2009 215 $a1 online resource (707 p.) 300 $aDescription based upon print version of record. 311 $a0-945090-96-X 311 $a0-470-51116-8 320 $aIncludes bibliographical references and index 320 $aIncludes bibliographical references and index. 327 $aLinker Strategies In Solid-Phase Organic Synthesis; Contents; Foreword; Preface; List of Contributors; About the Editor; Abbreviations; I INTRODUCTION; 1 General Overview; 1.1 Introduction, background and pivotal discoveries; 1.2 Fundamentals of conducting solid-phase organic chemistry; 1.2.1 Apparatus; 1.2.2 Typical solid supports; 1.2.3 Fluorous supports; 1.2.4 Linker strategies; 1.2.5 Challenges; 1.2.6 Linker groups; 1.3 Concluding comments; 1.4 Personal perspective and testimony: solid-phase Mannich chemistry; References; II TRADITIONAL LINKER UNITS FOR SOLID-PHASE ORGANIC SYNTHESIS 327 $a2 Electrophile Cleavable Linker Units2.1 Introduction; 2.2 Resins for use with electrophilic linkers; 2.3 Electrophile cleavable linkers; 2.3.1 Acid labile linkers; 2.4 Conclusion; References; 3 Nucleophile Cleavable Linker Units; 3.1 Introduction; 3.2 Linker units; 3.3 Nucleophilic labile linker units; 3.3.1 Cleavage by saponification or basic trans-esterification; 3.3.2 Cleavage by aminolysis; 3.3.3 Cleavage by hydrazinolysis; 3.3.4 Cleavage by Hydroxylamines; 3.3.5 Cleavage by other nucleophiles; 3.3.6 Linker cleavage by intramolecular nucleophilic reaction; 3.4 Conclusion; References 327 $a4 Cyclative Cleavage as a Solid-Phase Strategy4.1 Introduction; 4.2 C-N bond formation; 4.2.1 Cyclopeptides and cyclodepsipeptides; 4.2.2 Heterocycles, five-membered ring formation; 4.2.3 Heterocycles, six- and seven-membered ring formation; 4.3 C-O bond formation; 4.4 C-C bond formation; 4.5 Conclusion; References; 5 Photolabile Linker Units; 5.1 Introduction; 5.2 Linkers based on the ortho-nitrobenzyloxy function; 5.3 Linkers based on the ortho-nitrobenzylamino function; 5.4 Linkers based on the ?-substituted ortho-nitrobenzyl group; 5.5 Linkers based on the ortho-nitroveratryl group 327 $a5.6 Linkers based on the phenacyl group5.7 Linkers based on the para-methoxyphenacyl group; 5.8 Linkers based on the benzoin group; 5.9 Linkers based on the pivaloyl group; 5.10 Traceless linkers; 5.11 Other types of photolabile linker units; 5.12 Conclusion; References; 6 Safety-Catch Linker Units; 6.1 Introduction; 6.2 Activation of a carbonyl group by the inductive effect (I-) of an adjacent substituent; 6.2.1 Kenner-type safety-catch linker; 6.2.2 N-boc-activated safety-catch linker; 6.2.3 Sulfide/sulfone safety-catch linker; 6.2.4 Dpr(phoc) safety-catch linker 327 $a6.3 Activation by the mesomeric effect (M-) of the -X-Y=Z moiety adjacent to a carbonyl group6.3.1 Carbonyl activation by oxidative aromatization; 6.3.2 Carbonyl activation by indole ring formation; 6.3.3 Benzyl/phenyl-hydrazide safety-catch linker; 6.3.4 Dehydration activated safety-catch linker; 6.4 Activation by the positive mesomeric effect (M+) of the -X-Y=Z moiety adjacent to a N-acyl or O-alkyl group; 6.4.1 Benzhydryl-based safety-catch linker; 6.4.2 Indole-based safety-catch linker; 6.4.3 Nitrobenzyl alcohol-based safety-catch linker; 6.5 Aromatic SNAr substitution 327 $a6.6 Fragmentation by ?-elimination 330 $aLinker design is an expanding field with an exciting future in state-of-the-art organic synthesis. Ever-increasing numbers of ambitious solution phase reactions are being adapted for solid-phase organic chemistry and to accommodate them, large numbers of sophisticated linker units have been developed and are now routinely employed in solid-phase synthesis. Linker Strategies in Solid-Phase Organic Synthesis guides the reader through the evolution of linker units from their genesis in solid-supported peptide chemistry to the cutting edge diversity linker units that are defining a new 606 $aSolid-phase synthesis 606 $aOrganic compounds$xSynthesis 608 $aElectronic books. 615 0$aSolid-phase synthesis. 615 0$aOrganic compounds$xSynthesis. 676 $a547.2 700 $aScott$b Peter J. H$0934605 701 $aScott$b Peter J. H$0934605 801 0$bMiAaPQ 801 1$bMiAaPQ 801 2$bMiAaPQ 906 $aBOOK 912 $a9910140010803321 996 $aLinker strategies in solid-phase organic synthesis$92146235 997 $aUNINA