Miljkovic Carbohydrates

Synthesis, Mechanisms, and Stereoelectronic Effects
1. Auflage 2009
ISBN: 978-0-387-92265-2
Verlag: Springer
Format: PDF
Kopierschutz: 1 - PDF Watermark

E-Book, Englisch, 543 Seiten

All essential areas of basic synthetic carbohydrate chemistry are covered and appropriately described. In addition, this book explains the basic reaction mechanisms while taking into account modern concepts such as stereoelectronic principles.

Autoren/Hrsg.

Miljkovic, Momcilo

Inhaltsverzeichnis

1;Foreword;6
2;Preface;7
3;Contents;9
4;Introduction;14
4.1;Stereochemistry;15
4.2;Representation of Monosaccharides;15
4.3;The Nomenclature of Carbohydrates;22
4.4;References;38
5;Conformational Analysis of Monosaccharides;39
5.1;Conformational Analysis of Acyclic Hydrocarbons;40
5.2;Conformational Analysis of Acyclic (Aldehydo) Forms of Monosaccharides;43
5.3;Conformational Analysis of Cyclic (Lactol, Hemiacetal) Forms of Monosaccharides;45
5.4;Calculation of Conformational Energies of Pyranoses;53
5.5;References;65
6;Anomeric Effect;69
6.1;References;100
7;Isomerization of Sugars;106
7.1;Mutarotation;106
7.2;Anomerization;116
7.3;Lobry de Bruyn–Alberda van Ekenstein Transformation;119
7.4;References;120
8;Relative Reactivity of Hydroxyl Groups in Monosaccharides;123
8.1;Introduction;123
8.2;Selective Acylation (Esterification);124
8.3;Selective Alkylation and/or Arylation of Glycopyranosides;146
8.4;References;149
9;Cyclic Acetals and Ketals;153
9.1;Acetalation;158
9.2;Ketalation;160
9.3;Transacetalation and Transketalation;162
9.4;The Isomerization of Cyclic Acetals and Ketals;164
9.5;Removal of Acetal and Ketal Groups;167
9.6;References;173
10;Nucleophilic Displacement and the Neighboring Group Participation;178
10.1;Nucleophilic Displacement;178
10.2;Nucleophilic Displacements with Neighboring Group Participation;188
10.3;References;197
11;Anhydrosugars;200
11.1;1,6-Anhydrosugars (Glycosanes);200
11.2;1,4-Anhydrosugars;207
11.3;1,2-Anhydrosugars (Brigl’s Anhydrides);209
11.4;Anhydrosugars Not Involving the Anomeric Carbon;212
11.5;Rearrangements of Anhydrosugars;220
11.6;References;223
12;Amino Sugars;229
12.1;Ammonolysis of Oxiranes;229
12.2;Nucleophilic Displacement of Sulfonates (or Halides) with Nitrogen Nucleophiles;234
12.3;Glycosylamines and N-Glycosides;239
12.4;Acid-Catalyzed Hydrolysis of Purine and Pyrimidine Nucleosides;245
12.5;References;248
13;Oxidation of Monosaccharides;253
13.1;Selective Oxidations of Monosaccharides;253
13.2;Nonselective Oxidation of Secondary Hydroxyl Groups;256
13.3;DMSO–DCC Method (Pfitzner–Moffatt Oxidation);263
13.4;DMSO–Acetic Anhydride Method;266
13.5;DMSO–Phosphorus Pentoxide;271
13.6;DMSO–Sulfurtrioxide Pyridine (“Parikh–Doering” Oxidation);272
13.7;Chromium Trioxide Oxidation;274
13.8;Chromium Trioxide–Pyridine Oxidation;274
13.9;Chromium Trioxide–Acetic Acid;278
13.10;Pyridinium Chlorochromate;278
13.11;Nicotine Dichromate;280
13.12;Pyridinium Dichromate–Acetic Anhydride;280
13.13;Oxidation of Carbohydrates with the Cleavage of Carbohydrate Chain;281
13.14;References;292
14;Addition of Nucleophiles to Glycopyranosiduloses;299
14.1;The Addition of a Hydride Ion (Reduction);299
14.2;The Addition of Carbon Nucleophiles: Synthesis of Branched Chain Sugars;305
14.3;Synthesis of Branched Chain Sugars with Functionalized Branched Chain;316
14.4;References;326
15;Chemistry of the Glycosidic Bond;330
15.1;Introduction;330
15.2;Glycoside Synthesis;331
15.3;Cleavage of Glycosidic Bonds;381
15.4;References;413
16;Synthesis of Polychiral Natural Products from Carbohydrates;429
16.1;Macrolide Antibiotics: Erythronolides A and B;429
16.2;Thromboxane B2;444
16.3;Swainsonine;447
16.4;Biotin;449
16.5;Pseudomonic Acid C;451
16.6;Aplasmomycin;462
16.7;References;468
17;Carbohydrate-Based Antibiotics;474
17.1;Aminoglycoside Antibiotics;474
17.2;References;487
18;Higher-Carbon Monosaccharides;492
18.1;Introduction;492
18.2;Synthesis of Higher-Carbon Sugars;495
18.3;References;517
19;Author Index;522
20;Subject Index;543