Preparative Carbohydrate Chemistry

Preface\r......Page 1
Contents\r......Page 2
Contributors\r......Page 5
PART I\rSugar Derivatives......Page 7
1. Synthesis of Isopropylidene, Benzylidene and Related Acetals\r......Page 8
2. Dialkyl Dithioacetals of Sugars\r......Page 24
3. Regioselective Cleavage of O-Benzylidene Acetals to Benzyl Ethers\r......Page 33
4. Selective O-Substitution and Oxidation Using Stannylene Acetals and Stannyl Ethers\r......Page 41
PART II Selected Reactions in Carbohydrate Chemistry\r......Page 49
5. SN2-Type Halogenation and Azidation Reactions with Carbohydrate Triflates\r......Page 50
6. Direct Halogenation of Carbohydrate Derivatives\r......Page 59
7. Nucleophilic Displacement Reactions of Imidazole-1-Sulfonate Esters\r......Page 70
8. Free Radical Deoxygenation of Thiocarbonyl Derivatives of Alcohols\r......Page 82
9. Thiazole-Base One-Caron Extension of Carbohydrate Derivatives\r......Page 93
10. Selected Methods for Synthesis of Branched-Chain Sugars\r......Page 110
PART III Chemical Synthesis of O- and N-Glycosyl Compounds, and of Oligosaccharides\r......Page 138
11. O- and N-Glycopeptides: Synthesis of Selectively Deprotected Building Blocks\r......Page 139
12. Oligosaccharide Synthesis with Trichloroacetimidates\r......Page 148
13. Oligosaccharide Synthesis from Glycosyl Fluorides and Sulfides\r......Page 163
14. Oligosaccharide Synthesis by n-Pentenyl Glycosides\r......Page 176
15. Chemical Synthesis of Sialyl Glycosides\r......Page 185
16. Glycoside Synthesis Base on the Remote Activation Concept: An Overview\r......Page 197
17. Glycoside and Oligosaccharide Synthesis with Unprotected Glycosyl Donors Based on the Remote Activation Concept\r......Page 201
18. Oligosaccharide Synthesis by Remote Activation: O-Protected 3-Methoxy-2-pyridyloxy (MOP) Glycosyl Donors\r......Page 213
19. Oligosaccharide Synthesis by Remote Activation: O-Protected Glycosyl 2-thiopyridylcarbonate Donors\r......Page 222
20. Oligosaccharide Synthesis by Selective Anomeric Activation with MOP- and TOPCAT-Leaving Groups\r......Page 231
PART IV Enzymatic Synthesis of Sialic Acid, KDO, and Related Deoxyulosonic Acids, and of Oligosaccharides\r......Page 240
21. Enzymatic Synthesis of Carbohydrates\r......Page 241
22. Oligosaccharide Synthesis by Enzimatic Glycosidation\r......Page 249
PART V Synthesis of C-Glycosyl Compounds\r......Page 259
23. C-Glycosyl Compounds from Free Radical Reactions\r......Page 260
24. Synthesis of Glycosylarenes\r......Page 270
PART VI Carbocycles from Carbohydrates\r......Page 278
25. Functionalized Carbocylic\rDerivatives from Carbohydrates: Free Radical and Organometallic Methods......Page 279
26. The Conversion of Carbohydrates to Cyclohexane Derivatives\r......Page 291
PART VII Total Synthesis of Sugars from Nonsugars\r......Page 303
27. Total Synthesis of Amino Sugars\r......Page 304
28.\rTotal Synthesis of Sugars......Page 314
Index\r......Page 325