| Foreword / Derek Horton | xiii |
| Foreword / Paul Kosma | xv |
| Foreword / Bert Fraser-Reid | xvii |
| Introduction | xix |
| Contributors | xxiii |
pt. I | Synthetic Methods | |
1. | Acetolysis of 6-Deoxysugars Controlled by Armed---Disarmed Effect / Michalangelo Parrilli | 3 |
| Experimental Methods | 4 |
| General Methods | 4 |
| Acetolysis Procedure | 6 |
| Acknowledgments | 7 |
| References | 10 |
2. | NaH/Im2SO2-Mediated Preparation of Hex-2- and Hex-3-Enopyranoside Enol Ethers / Marie-Christine Scherrmann | 11 |
| Experimental Methods | 16 |
| General Methods | 16 |
| Methyl 2,6-Di-O-Benzyl-4-Deoxy-3-O-Naphthylmethyl-β-D-threo-Hex-3-Enopyranoside(13) | 16 |
| Methyl 2-O-Benzyl-4-Deoxy-3-O-p-Methoxybenzyl-6-O-Methoxymethyl-β-D-threo-Hex-3-Enopyranoside (15) | 17 |
| 3-Azidopropyl 2-Acetamido-3,6-Di-O-Benzyl-2,4-Dideoxy-β-D-threo-Hex-3-Enopyranosyl-(1 [→] 4)-2,3,6,-Tri-O-Benzyl-β-D-Glucopyranosyl-(1 [→] 2)-3,4-Di-O-Benzyl-α-L-Rhamnopyranoside (17) | 17 |
| Methyl 3,4,6-Tri-O-Benzyl-2-Deoxy-β-D-threo-Hex-2-Enopyranoside (19) | 18 |
| 2-Deoxy-3,4-O-Isopropylidene-6-O-Trityl-β-D-threo-Hex-2-Enopyranosyl-(1 [→] 4)-2,3:5,6-Di-O-Isopropylidene-Aldehydo-D-Glucose Dimethyl Acetal (21) | |
| Methyl 3,4-Di-O-Benzyl-2,6-Dideoxy-α-L-threo-Hex-2-Enopyranoside (23) | 19 |
| References | 26 |
3. | Enhancement of the Rate of Purdie Methylation by Me2S Catalysis / Pavol Kovac | 27 |
| Experimental Methods | 29 |
| General Methods | 29 |
| General Procedure | 29 |
| Methylation of Methyl 3-O-Benzyl-β-D-Galactopyranoside (1) | 30 |
| Methylation of Methyl 6-O-Trityl-β-D-Galactopyranoside (3) | 31 |
| Methylation of Methyl 6-O-Trityl-α-D-Glucopyranoside (5) | 32 |
| Methylation of Methyl 2,3-Di-O-Benzyl-6-O-Benzoyl-β-D-Glucopyranoside (7) | 33 |
| Acknowledgment | 35 |
| References | 42 |
4. | Synthesis of Oligosaccharides by Preactivation-Based Chemoselective Glycosylation of Thioglycosyl Donors / Xuefei Huangs | 43 |
| Experimental Methods | 45 |
| General Methods | 45 |
| P-Toluenesulfenyl Chloride (1)25 | 46 |
| P-Tolyl 6-O-(2,3,4-Tri-O-Benzoyl-6-O-Tert-Butyldiphenylsilyl-β-D-Glucopyranosyl)-2,3,4-Tri-O-Benzyl-1-Thio-β-D-Glucopyranoside (4) | 46 |
| Methyl-2-O-Benzoyl-3-O-Benzyl-4-O-tert-Butyldimethylsilyl)-6-0-p-Methoxybenzyl-β-D-Glucopyranosyl-(1 [→] 3)-4,6-O-Benzylidene-2-Deoxy-2-N-Phthalimido-β-D-Galactopyranosyl-(1 [→] 4)-2,3-Di-O-Benzyl-6-O-p-Methoxybenzyl-β-D-Glucopyranoside (8) | 47 |
| Acknowledgment | 48 |
| References | 50 |
5. | The Use of Hypophosphorous Acid in Radical Chain Deoxygenation of Carbohydrates / Alice Voss | 53 |
| Experimental Methods | 56 |
| General Method | 56 |
| Methyl 2,3-O-Isopropylidene-4-O-[(Methylsulfanyl)thiocarbonyl]-6-O-Triphenylmethyl-α-D-Mannopyranoside (2) | 57 |
| Methyl 4-Deoxy-2,3-O-Isopropylidene-6-O-Triphenylmethyl-α-D-Lyxo-Hexopyranoside (3) | 57 |
| 1,2:5,6-Di-O-Isopropylidene-3-O-[(Methylsulfanyl)thiocarbonyl]-α-D-Glucofuranose (5) | 58 |
| 3-Deoxy-1,2:5,6-Di-O-Isopropylidene-α-D-Ribo-Hexofuranose (6) | 58 |
| 1,2:4,5-Di-O-Isopropylidene-3-O-[(Methylsulfanyl)thiocarbonyl]-β-D-Fructopyranose (8) | 58 |
| 3-Deoxy-1,2:4,5-Di-0-Isopropylidene-β-D-Erythro-Hex-2-Ulopyranose (9) | 59 |
| 1,6-Anhydro 4-O-Benzyl-2-Deoxy-2-C-Methyl-3-O-[(Methylsulfanyl)thiocarbonyl]-β-D-Glucopyranose (11) | 59 |
| 1,6-Anhydro 4-O-Benzyl-2,3-Dideoxy-2-C-Methyl-β-D-Ribo-Hexopyranose (12) | 59 |
| References | 63 |
6. | Diphenylsulfoxide-Trifluoromethanesulfonic Anhydride: A Potent Activator for Thioglycosides / Gijsbert A. van der Marel | 67 |
| Experimental Methods | 68 |
| General Methods | 68 |
| Methyl (4-O-Acetyl-2,3-Di-O-β-D-Mannopyranosyl)-(1 [→] 6)-(Methyl 2,3,4-Tri-O-Benzyl-α-D-Glucopyranosid)uronate (6) | 69 |
| Acknowledgments | 70 |
| References | 71 |
7. | Preparation of Glycosyl Chlorides from Glycopyranoses/Glycopyranoses under Mild Conditions / Kwok-Kong T. Mong | 73 |
| Introduction | 73 |
| General TCT/DMF Chlorination Protocols | 75 |
| Experimental Methods | 75 |
| General Methods | 75 |
| TCT/DMF Chlorination Protocol A for Preparation of Glycosyl Chlorides 1a and 2a | 76 |
| TCT/DMF Chlorination Protocol B for Preparation of Glycosyl Chlorides 3a and 4a | 76 |
| 2,3,4,6-Tetra-O-Acetyl-α-D-Glucopyranosyl Chloride (1a) | 76 |
| 2,3,4,6-Tetra-O-Acetyl-α-D-Mannopyranosyl Chloride (2a) | 77 |
| 2,3,4,6-Tetra-O-Benzyl-α-D-Galactopyranosyl Chloride (3a) | 77 |
| 2,3:5,6-Di-O-Isopropylidene-α-D-Mannofuranosyl Chloride (4a) | 77 |
| Acknowledgment | 78 |
| References | 81 |
8. | C-Glycosylation Starting from Unprotected O-Glycosides / Francesco Nicotra | 83 |
| Experimental Methods | 84 |
| General Methods | 84 |
| 3-(α-D-Galactopyranosyl)prop-l-Ene (2) | 85 |
| Bicyclic Iodoethers (3) | 85 |
| Methyl (2R)-2-Acetamido-3-(α-D-Galactopyranosylpropylthio) propanoate (4) | 85 |
| Acknowledgments | 86 |
| References | 89 |
9. | Palladium-Catalyzed Sonogashira Coupling on p-lodophenyl α-D-Mannopyranoside / Mohamed Touaibia | 91 |
| Experimental Methods | 92 |
| General Methods | 92 |
| 3-[4-(2,3,4,6-Tetra-O-Acetyl-α-D-Mannopyranosyloxy)phenyl]prop-2-Yn-l-ol (2) | 92 |
| Acknowledgments | 93 |
| References | 94 |
10. | Synthesis by "Click Chemistry" of an α-D-Mannopyranoside Having a 1,4-Disubstituted Triazole as Aglycone / Mohamed Touaibia | 95 |
| Experimental Methods | 96 |
| General Methods | 96 |
| Methyl2-{[4-(2,3,4,6-Tetra-O-Acetyl-α-D-Mannopyranosyloxy)methyl]-1H-l,2,3-Triazol-l-yl]}Acetate (2) | 96 |
| Acknowledgments | 97 |
| References | 98 |
11. | Synthesis of Methyl Glycuronates by Chemo-and Regioselective TEMPO/BAIB-Oxidation / Jeroen D.C. Codee | 99 |
| Experimental Methods | 101 |
| General Methods | 101 |
| Phenyl3-O-Benzoyl-2-Deoxy-2-Phthalimido-1-Thio-β-D- Glucopyranosyluronic Acid (2) | 102 |
| Methyl(Phenyl3-O-Benzoyl-2-Deoxy-2-Phthalimido-1-Thio-β-D-Glucopyranoside) Uronate (3) | 102 |
| Acknowledgments | 103 |
| References | 104 |
12. | Synthesis of Sugar Nucleotides: A Phosphoramidite Approach / Gijsbert A. van der Marel | 107 |
| Experimental Methods | 109 |
| General Methods | 109 |
| Uridine5'-(2-Acetamido-2-Deoxy-α-D-GlucopyranosylDiphosphate)Disodium Salt(5) | 109 |
| References | 112 |
13. | Conversion of N-2,2,2-Trichloroethoxycarbonyl-Protected 2-Aminoglycosides into N-Alkylated 2,3-N, O-Carbonyl Glycosides / Thomas Ziegler | 113 |
| Experimental Methods | 115 |
| General Methods | 115 |
| General Procedure | 115 |
| 2-Trimethylsilylethyl 4,6-O-Benzylidene-2-Deoxy-2-(2,2,2-Trichlorethoxycarbamido)-β-D-Glucopyranoside (1) | 115 |
| 2-Trimethylsilylethyl 2-Amino-2-N-Benzyl-4,6-O-Benzylidene-2,3-N, O-Carbonyl-2-Deoxy-β-D-Glucopyranoside (2) | 116 |
| Phenyl 4,6-O-Benzylidene-2-Deoxy-1-Thio-2-(2,2,2-Trichlorethoxycarbamido)-β-D-Glucopyranoside (3) | 116 |
| Phenyl 2-Amino-2-N-Benzyl-4,6-O-Benzylidene-2,3-N, O-Carbonyl-2- Deoxy-1-Thio-β-D-Glucopyranoside (4) | 117 |
| Phenyl 2-Amino-4,6-O-Benzylidene-2,3-N, o-Carbonyl-2-Deoxy-2-N-(4-Nitrobenzyl)-1-Thio-β-D-Glucopyranoside (5) | 117 |
| Phenyl 2-Amino-4,6-O-Benzylidene-2,3-N, o-Carbonyl-2-Deoxy-2-N-(4-Methoxybenzyl)-1-Thio-β-D-Glucopyranoside (6) | 117 |
| Phenyl 2-Amino-4,6-O-Benzylidene-2,3-N, o-Carbonyl-2-Deoxy-2-N-(Prop-2-Enyl)-1-Thio-β-D-Glucopyranoside (7) | 118 |
| Phenyl 2-Amino-4,6-O-Benzylidene-2,3-N, o-Carbonyl-2-Deoxy-2-N-(Prop-2-Ynyl)-1-Thio-β-D-Glucopyranoside (8) | 118 |
| Phenyl 4,6-O-Benzylidene-2-Deoxy-1-Thio-2-(2,2,2-Trichlorethoxycarbamido)-β-D-Galactopyranoside (9) | 118 |
| Phenyl 2-Amino-2-N-Benzyl-4,6-O-Benzylidene-2,3-N, o-Carbonyl-2-Deoxy-l-Thio-β-D-Galactopyranoside (10) | 119 |
| References | 127 |
14. | TIBAL-lnduced Rearrangement: Synthesis of gem-Difluorocarbagalactose / Yves Bleriot | 129 |
| Experimental Methods | 131 |
| General Methods | 131 |
| Rearrangement of 1 into 2,3,4-Tri-O-Benzyl-6,7,8-Trideoxy-5a-Difluoro-5a-Carba-α-D-Galacto-Oct-6-Ynopyranose (4) and 2,3,4-Tri-O-Benzyl-6,7,8-Trideoxy-5a-Difluoro-5a-Carba-β-D-Galacto-Oct-6-Ynopyranose (5) | 132 |
| Acknowledgment | 132 |
| References | 135 |
15. | Pyranose-Fused Butenolides: An Expedient Preparation from Furanose Synthons / Amelia Pilar Rauter | 137 |
| Experimental Methods | 140 |
| General Methods | 140 |
| 1,2:5,6-Di-O-Isopropylidene-α-D-Ribo-Hexofuranosid-3-Ulose (1) | 141 |
| 3-Deoxy-3-C-[(Z)-(Ethoxycarbonyl)methylene]-1,2:5,6-Di-O-Isopropylidene-α-D-Ribo-Hexofuranose (2) and 3-Deoxy-3-C-[(E)-(Ethoxycarbonyl)methylene]-1,2:5,6-Di-O-Isopropylidene-α-D-Ribo-Hexofuranose (3) | 141 |
| 3-C-(Carboxymethylene)-3-Deoxy-D-Ribo-Hexopyranose-3', 2-Lactone (4) | 141 |
| 3-Deoxy-3-C-[(Z)-(Ethoxycarbonyl)methylene]-1,2-O-Isopropylidene-α-D-Ribo-Hexofuranose (5) | 142 |
| 3-Deoxy-3-C-[(Z)-(Ethoxycarbonyl)methylene]-1,2-O-Isopropylidene-6-O-Pivaloyl-α-D-Ribo-Hexofuranose (6) and 3-Deoxy-3-C-[(Z)-(Ethoxycarbonyl)methylene]-1,2-O-Isopropylidene-5,6-Di-O-Pivaloyl-α-D-Ribo-Hexofuranose (7) | 142 |
| 3-C-(Carboxymethylene)-3-Deoxy-6-O-Pivaloyl-D-Ribo-Hexopyranose-3',2-Lactone (8) | 143 |
| 1,4,6-Tri-O-Acetyl-3-C-(Carboxymethylene)-3-Deoxy-D-Ribo-Hexopyranose-3',2-Lactone (9) | 143 |
| 5-O-Tert-Butyldimethylsilyl-1,2-O-Isopopylidene-α-D-Erythro-Pentofuranos-3-Ulose (10) | 144 |
| 5-0-Tert-Butyldimethylsily1-3-Deoxy-3-C-[(Z)-(Ethoxycarbonyl)methylene]-1,2-O-Isopropylidene-α-D-Erythro-Pentofuranose (11) and 5-O-Tert-Butyldimethylsilyl-3-Deoxy-3-C-[(E)-(Ethoxycarbonyl)methylene]-1,2-O-Isopropylidene-α-D-Erythro-Pentofuranose (12) | 144 |
| 3-C-(Carboxymethylene)-3-Deoxy-D-Erythro-Pentopyranose-3',2-Lactone (13) | 145 |
| Acknowledgment | 145 |
| References | 157 |
16. | Glycal Dimerization with High Diastereoselectivity / Katja Michael | 159 |
| Experimental Methods | 160 |
| General Methods | 160 |
| General Method for the Dimerization of Glycals | 161 |
| 1,3,4,6-Tetra-O-Acetyl-2-C-(4,6-Di-O-Acetyl-2,3-Dideoxy-α-D-Erythro-Hex-2-Enopyranosyl)-2-Deoxy-α/β-D-Glucopyranose (2a, 2b) | 162 |
| Acknowledgments | 164 |
| References | 166 |
17. | Regioselective Debenzylation of C-Glycosylpropene / Francesco Nicotra | 167 |
| Experimental Methods | 168 |
| General Methods | 168 |
| General Procedure for Iodocyclization | 169 |
| β-Elimination | 169 |
| 3-C-(3,4,6-Tri-O-Benzyl-α-D-Glucopyranosyl)Prop-1-Ene (3) | 169 |
| 3-C-(3,4,6-Tri-O-Benzyl-α-D-Fructofuranosyl)Prop-1-Ene (6) | 170 |
| Acknowledgment | 171 |
| References | 173 |
18. | Synthesis of Azido-Functionalized Carbohydrates for the Design of Glycoconjugates / Sebastien Vidal | 175 |
| Experimental Methods | 176 |
| General Methods | 176 |
| General Procedure for Glycosylation | 177 |
| 1-Azido-3,6-Dioxaoct-8-yl 2,3,4,6-Tetra-O-Acetyl-β-D-Galactopyranoside 2 | 177 |
| 1-Azido-3,6-Dioxaoct-8-yl 2,3,6,2',3',4',6'-Hepta-O-Acetyl-β-Lactoside 4 | 178 |
| Acknowledgments | 178 |
| References | 180 |
19. | Synthesis of Thioglycosides and Thioimidates from Glycosyl Halides / Alexei V. Demchenko | 181 |
| Experimental Methods | 182 |
| 1,3-Benzoxazol-2-yl 2,3,4,6-Tetra-O-Acetyl-l-Thio-β-D-Glucopyranoside (3) | 182 |
| Methyl (Phenyl 5-Acetamido-4,7,8,9-Tetra-O-Acetyl-3,5-Dideoxy-2-Thio-D-Glycero-α-D-Galato-Non-2-Ulopyranosid)onate (6) | 183 |
| Acknowledgments | 183 |
| References | 185 |
20. | Synthesis of Thioglycosides and Thioimidates from Peracetates / Alexei V. Demchenko | 187 |
| Experimental Methods | 189 |
| General Methods | 189 |
| Phenyl 2,3.4,6-Tetra-O-Acetyl-1-Thio-β-D-Glucopyranoside (2) | 189 |
| 4,5-Dihydro-1,3-Thiazol-2-yl 2,3,4,6-Tetra-O-Acetyl-1-Thio-β-D-Glucopyranoside (3) | 190 |
| Ethyl 2,3,4,6-Tetra-O-Acetyl-1-Thio-β-D-Glucopyranoside (4) | 190 |
| P-Tolyl 2,3.4.6-Telra-O-Acetyl-1-Thio-β-D-Glucopyranoside (5) | 191 |
| Acknowledgment | 191 |
| References | 195 |
pt. II | Synthetic Intermediates | |
21. | 2-Acetamido-4,6-O-BenzyIidene-2-Deoxy-D-GIucopyranose / Sebastien Vidal | 199 |
| Experimental Methods | 200 |
| General Methods | 200 |
| 2-Acetamido-4,6-O-Benzylidene-2-Deoxy-D-Glucopyranose (2) | 200 |
| Acknowledgment | 202 |
| References | 203 |
22. | Synthesis of 1,3,4,6-Tetra-O-Acetyl-2-Azido-2-Deoxy-α,β-D-Glucopyranose and 2-Azido-4,6-O-Benzylidene-2-Deoxy-α,β-D-Glucopyranose / Manuel Martin-Lomas | 205 |
| Experimental Methods | 206 |
| General Methods | 206 |
| Preparation of Trifluoromethanesulfonyl Azide (TfN3) Solution | 207 |
| 1,3,4,6-Tetra-O-Acetyl-2-Azido-2-Deoxy-α,β-D-Glucopyranose (2) | 207 |
| 2-Azido-4,6-O-Benzylidene-2-Deoxy-α,β-D-Glucopyranose (3) | 208 |
| References | 211 |
23. | An Easy Access to 2,3,4,6-Tetra-O-Benzyl-D-Galactopyranose and 2,3,6-Tri-O-Benzyl-D-Glucopyranose / Lorenzo Guazzelli | 213 |
| Experimental Methods | 214 |
| General Methods | 214 |
| Benzyl 2,3,4,6-Tetra-O-Benzyl-β-D-Galactopyranosyl-(1 [→] 4)-2,3,6-Tri-O-Benzyl-β-D-Glucopyranoside (II) | 215 |
| 2,3,4,6-Tetra-O-Benzyl-D-Galactopyranose (IV), 2,3,6-Tri-O-Benzyl-D-Glucopyranose (V) and 1-O-Acetyl-2,3,4,6-Tetra-O-Benzyl-β-D-Galactopyranose (III) | 216 |
| References | 220 |
24. | Benzyl 2,3,6,2',3',6'-Hexa-O-Benzyl-β-Cellobioside / Pavol Kovaac | 221 |
| Experimental Methods | 222 |
| General Methods | 222 |
| Benzyl 2,3,6,2',3'-Penta-O-Benzyl-4',6'-O-Benzylidene-α-Cellobioside (2A) and Benzyl 2,3,6,2',3'-Penta-O-Benzyl-4',6'-O-Benzylidene-β-Cellobioside (2B) | 223 |
| Benzyl 2,3,6,2',3',6'-Hexa-O-Benzyl-β-Cellobioside (3) and Benzyl 2,3,6,2',3',4'-Hexa-O-Benzyl-β-Cellobioside (9) | 224 |
| Acknowledgment | 225 |
| References | 230 |
25. | One-Step Syntheses of 1,2,3,5,6-Penta-O-Benzoyl-α,β-D-Galactofuranose and 1,2,3,5-Tetra-O-Benzoyl-α,β-D-Arabinofuranose / Rosa M. de Lederkremer | 231 |
| Experimental Methods | 233 |
| General Methods | 233 |
| 1,2,3,5,6-Penta-O-Benzoyl-α,β-D-Galactofuranose (1α and 1β) | 233 |
| 1,2,3,5-Tetra-O-Benzoyl-α,β-D-Arabinofuranose (2αβ), 1,2,3,5-Tetra-O-Benzoyl-α-D-Arabinofuranose (2α) and 1,2,3,4-Tetra-O-Benzoyl-α-D-Arabinopyranose (3) | 234 |
| Acknowledgments | 235 |
| References | 237 |
26. | Stereoselective Synthesis of α-C-Sialyl Compounds / Robert J. Linhardt | 239 |
| Introduction | 239 |
| Experimental Methods | 240 |
| General Methods | 240 |
| SmI2 Mediated C-Sialylation: 4,4-Dimethyl-l-[Methyl (5-Acetamido-4,7,8,9-Tetra-O-Acetyl-3,5-Dideoxy-D-Glycera-α-D-Galacto-Non-2-Ulopyranosyl)onate]cyclohexanol (3) | 240 |
| References | 242 |
27. | Synthesis of O-Acetylated N-Acetylneuraminic Acid Glycal / Leonid O. Kononov | 245 |
| Experimental Methods | 246 |
| General Methods | 246 |
| Methyl (5-Acetamido-4,7,8,9-Tetra-O-Acetyl-3,5-Dideoxy-β-D-Glycero-D-Galacto-Non-2-Ulopyranosyl)onate Chloride (2) | 246 |
| Methyl (5-Acetamido-4,7,8,9-Tetra-O-Acetyl-3,5-Dideoxy-2,6-Anhydro-D-Glycero-D-Galacto-Non-2-Enopyranos)onate (3) | 249 |
| Acknowledgment | 250 |
| References | 250 |
28. | Substituted Benzyl Glycosides of N-Acetylneuraminic Acid / N.V. Bovin | 251 |
| Experimental Methods | 253 |
| General Methods | 253 |
| Methyl {4-[(Tert-Butyloxycarbonyl)glycylarmido]benzyl 5-Acetamido-4,7,8,9-Tetra-O-Acetyl-3,5-Dideoxy-D-Glycero-D-Galacto-Non-2-Ulopyranosid}onate (3) | 253 |
| 4-[(Tert-Butyloxycarbonyl)glycylamido]benzyl 5-Acetamido-3,5-Dideoxy-D-Glycero-D-Galacto-Non-2-Ulopyranosidonic Acid (5) | 256 |
| 4-(Glycylamido)benzyl 5-Acetamido-3,5-Dideoxy-D-Glycero-D-Galacto-Non-2-Ulopyranosidonic Acid (6) | 256 |
| 4-[(4-Nitrophenoxy)adipoylglycylamido]benzyl 5-Acetamido-3,5-Dideoxy-D-Glycero-D-Galacto-Non-2-Ulopyranosidonic Acid (8) | 257 |
| Acknowledgment | 257 |
| References | 257 |
29. | Synthesis of 1,5-Di-C-Alkyl 1,5-Iminoxylitols Related to 1-Deoxynojirimycin / Jean-Bernard Behr | 259 |
| Introduction | 259 |
| Experimental Methods | 261 |
| General Methods | 261 |
| 1,5-Di-(1/2-Benzotriazolyl)-N-Benzyl-1,5-Dideoxy-1,5-Iminoxylitol (4) | 261 |
| 2,3,4-Tri-O-Acetyl-1,5-Di-C-Allyl-N-Benzyl-1,5-Dideoxy-1,5-Iminoxylitol (5) | 262 |
| Meso-(1R,5S)-, Meso-(1S,5R), and Rac-(1R,5R)-2,3,4-Tri-O-Acetyl-1,5-Di-C-Allyl-1,5-Dideoxy-1,5-Iminoxylitol (6a, 6b, and 6c) | 262 |
| Acknowledgment | 263 |
| References | 267 |
30. | Synthesis of 1,6-Anhydro 2,3,5-Tri-O-Benzoyl-α-D-Galactofuranose / Nirmolendu Roy | 269 |
| Experimental Methods | 270 |
| General Methods | 270 |
| 6-O-Benzyl-1,2:3,4-Di-O-Isopropylidene-α-D-Galactopyranose (2) | 270 |
| Methyl 2,3,5-Tri-O-Benzoyl-6-O-Benzyl-β-D-Galactofuranoside (4) | 270 |
| 1,6-Anhydro-2,3,5-Tri-O-Benzoyl-α-D-Galactofuranose (5) | 271 |
| 1,6-Anhydro-α-D-Galactofuranose (6) | 271 |
| 1,6-Anhydro-2,3,5-Tri-O-Acetyl-α-D-Galactofuranose (7) | 271 |
| Acknowledgment | 271 |
| References | 274 |
31. | Synthesis of Prop-2-Ynyl 2,3,4,6-Tetra-O-Acetyl-α-D-Mannopyranoside / Rene Roy | 275 |
| Experimental Methods | 276 |
| General Methods | 276 |
| Prop-2-Ynyl 2,3,4,6-Tetra-O-Acetyl-α-D-Mannopyranoside (2) | 276 |
| Acknowledgments | 277 |
| References | 278 |
32. | Synthesis of 3-C-(2,3,4,6-Tetra-O-Acetyl-β-D-Galactopyranosyl) prop-1-Ene / Rene Roy | 279 |
| Experimental Methods | 280 |
| General Methods | 280 |
| 2,3,4,6-Tetra-O-Acetyl-α-D-Galactopyranosyl Bromide (1) | 280 |
| 3-C-(2,3.4,6-Tetra-O-Acetyl-β-D-Galactopyranosyl)Prop-l-Ene (2) | 281 |
| Acknowledgments | 281 |
| References | 282 |
33. | Synthesis of (E)-Methyl 4-(2,3,4,6-Tetra-O-Acetyl-β-D-Galactopyranosyl) but-2-Enoate by Cross-Metathesis Reaction / Rene Roy | 285 |
| Experimental Methods | 286 |
| General Methods | 286 |
| (E)-Methyl 4-(2,3,4,6-Tetra-O-Acetyl-β-D-Galactopyranosyl)but-2- Enoate (2) | 286 |
| Acknowledgment | 287 |
| References | 288 |
34. | Preparation of O-β-D-Galactopyranosyl-hydroxylamine / Rene Roy | 289 |
| Experimental Methods | 290 |
| General Methods | 290 |
| O-(2,3,4,6-Tetra-O-Acetyl-β-D-Galactopyranosyl)-N-Hydroxysuccinimide (2) | 290 |
| O-β-D-Galactopyranosylhydroxylamine (3) | 291 |
| Acknowledgments | 291 |
| References | 293 |
35. | Synthesis of 2,3,4,6-Tetra-O-Acetyl-1,5-Anhydro-D-Lyxo-Hex-1-Enitol and Its Conversion into a Hex-3-Enopyranosid-2-Ulose Analogue of Levoglucosenone / Oscar Varela | 295 |
| Experimental Methods | 296 |
| General Methods | 296 |
| 2,3,4,6-Tetra-O-Acetyl-1,5-Anhydro-D-Lyxo-Hex-1-Enitol (3) | 297 |
| Benzyl 3,4-Dideoxy-α-D-Glycero-Hex-3-Enopyranosid-2-Ulose (4) | 298 |
| Acknowledgments | 298 |
| References | 301 |
36. | Efficient Synthesis of Methyl(Allyl 4-O-Acyl-2,3-Di-O-Benzyl-β-D-Galactopyranosid) uronates from D-Galacturonic Acid / Christian Vogel | 303 |
| Experimental Methods | 306 |
| General Methods | 306 |
| 1,2,3,4-Tetra-O-Acetyl-α-D-Galactopyranuronic Acid (11) | 307 |
| Methyl 1,2,3,4-Tetra-O-Acetyl-α-D-Galactopyranuronate (12) | 308 |
| Methyl 2,3,4-Tri-O-Acetyl-α-D-Galactopyranosyluronate Bromide (13) | 308 |
| Methyl (Allyl 2,3,4-Tri-O-Acetyl-β-D-Galactopyranosid)uronate (14) | 308 |
| Methyl (Allyl β-D-Galactopyranosid)uronate (19) | 309 |
| Regioselective Ring Opening in Orthoester Structures 20 and 21 | 309 |
| Methyl (Allyl 4-O-Acetyl-β-D-Galactopyranosid)uronate (22) | 309 |
| Methyl (Allyl 4-O-Benzoyl-β-D-Galactopyranosid)uronate (23) | 310 |
| Benzylation of Compounds 22 and 23 | 310 |
| Methyl (Allyl 4-O-Acetyl-2,3-Di-O-Benzyl-β-D-Galactopyranosid)uronate (1) | 310 |
| Methyl (Allyl 4-O-Benzoyl-2,3-Di-O-Benzyl-β-D-Galactopyranosid)uronate (2) | 310 |
| Methyl (Allyl 2,3-Di-O-Benzyl-β-D-Galactopyranosid)uronate (5) | 311 |
| References | 326 |
37. | Methyl(Ethyl 2,3,5-Tri-O-Benzoyl-1-Thio-α,β-D-Galactofuranosid)uronate / Nirmolendu Roy | 327 |
| Experimental Methods | 329 |
| General Methods | 329 |
| Tert-Butyl 1,2:3,4-Di-O-Isopropylidene-α-D-Galactopyranuronate (2) | 330 |
| Methyl (Methyl α,β-D-Galactofuranosid)uronate (3) | 330 |
| Methyl (Methyl α-D-Galactofuranosid)uronate (3α) | 330 |
| Methyl (Methyl β-D-Galactofuranosid)uronate (3β) | 330 |
| Methyl (Methyl 2,3,5-Tri-O-Benzoyl-α,β-D-Galactofuranosid)uronate (4) | 330 |
| Methyl (Methyl 2,3,5-Tri-O-Benzoyl-α-D-Galactofuranosid)uronate (4α) | 331 |
| Methyl (Methyl 2,3,5-Tri-O-Benzoyl-β-D-Galactofuranosid)uronate (4β) | 331 |
| Methyl 1-O-Acetyl-2,3,5-Tri-O-Benzoyl-α,β-D-Galactofuranuronate (5) | 331 |
| Methyl 1-O-Acetyl-2,3,5-Tri-O-Benzoyl-α-D-Galactofuranuronate (5α) | 331 |
| Methyl 1-O-Acetyl-2,3,5-Tri-O-Benzoyl-β-D-Galactofuranuronate (5β) | 332 |
| Methyl (Ethyl 2,3,5-Tri-O-Benzoyl-1-Thio-α,β-D-Galactofuranosid)uronate (6) | 332 |
| Methyl (Ethyl 2,3,5-Tri-O-Benzoyl-1-Thio-α-D-Galactofuranosid)uronate (6α) | 332 |
| Methyl (Ethyl 2,3,5-Tri-O-Benzoyl-1-Thio-β-D-Galactofuranosid)uronate (6β) | 332 |
| References | 339 |
38. | P-Tolyl 2,3,5-Tri-O-Benzoyl-1-Thio-α-D-Arabinofuranoside: A Useful Thioglycoside Building Block In The Synthesis Of Oligoarabinofuranosides / Todd L. Lowary | 341 |
| Experimental Methods | 342 |
| General Methods | 342 |
| P-Tolyl 2,3,5-Tri-O-Benzoyl-1-Thio-α-D-Arabinofuranoside | 343 |
| Waste Disposal Information | 344 |
| Acknowledgments | 344 |
| References | 347 |
39. | Ethylene Dithioacetals of Common Hexoses / Maria Teresa Barros | 349 |
| Experimental Methods | 350 |
| General Methods | 350 |
| General Procedure | 350 |
| D-Galactose Ethylene Dithioacetal (1) | 350 |
| D-Glucose Ethylene Dithioacetal (2) | 350 |
| D-Mannose Ethylene Dithioacetal (3) | 351 |
| References | 354 |
40. | Preparation of 2,6-Anhydro-Aldose Tosylhydrazones / David Goyard | 355 |
| Experimental Methods | 357 |
| General Methods | 357 |
| General Procedure | 357 |
| 2,6-Anhydro-3,4,5,7-Tetra-O-Benzoyl-D-Glycero-D-Gulo-Heptose Tosylhydrazone (2a) | 358 |
| 3,4,5,7-Tetra-O-Acetyl-2,6-Anhydro-D-Glycero-D-Gulo-Heptose Tosylhydrazone (2b) | 358 |
| 3,4,5,7-Tetra-O-Acetyl-2,6-Anhydro-D-Glycera-L-Manno-Heptose Tosylhydrazone (2c) | 358 |
| 4,5,7-Tri-O-Acetyl-2,6-Anhydro-3-Deoxy-3-Phthalimido-D-Glycero-D-Gulo-Heptose Tosylhydrazone (2d) | 359 |
| 3,4,5-Tri-O-Acetyl-2,6-Anhydro-D-Manno-Hexose Tosylhydrazone (2e) | 359 |
| Acknowledgments | 359 |
| References | 365 |
41. | Preparation of Exo-Glycals from (C-Glycopyranosyl) formaldehyde Tosylhydrazones / David Goyard | 367 |
| Experimental Methods | 369 |
| General Methods | 369 |
| General Procedure | 369 |
| 2,6-Anhydro-3,4,5,7-Tetra-O-Benzoyl-1-Deoxy-D-Gluco-Hept-1-Enitol (2a) | 370 |
| 3,4,5,7-Tetra-O-Acetyl-2,6-Anhydro-1-Deoxy-D-Galacto-Hept-1-Enitol (2b) | 370 |
| 4,5,7-Tri-O-Acetyl-2,6-Anhydro-1,3-Dideoxy-3-Phthalimido-D-Gluco-Hept-1-Enitol (2c) | 370 |
| 3,4,5-Tri-O-Acetyl-2,6-Anhydro-1-Deoxy-D-Arabino-Hex-1-Enitol (2d) | 370 |
| Acknowledgments | 371 |
| References | 375 |
42. | Synthsis of O-(6-Deoxy-α-and β-L-Galactopyranosyl) Hydroxylamines (α-and β-L-Fucopyranosyl-hydroxylamines) / Olivier Renaudet | 377 |
| Experimental Methods | 378 |
| General Methods | 378 |
| O-(2,3,4-Tri-O-Acetyl-6-Deoxy-α-L-Galactopyranosyl)-N-Hydroxyphthalimide (2) and O-(2,3,4-Tri-O-Acetyl-6-Deoxy-β-L-Galactopyranosyl)-N-Hydroxyphthalimide (3) | 379 |
| O-(6-Deoxy-α-L-Galactopyranosyl)Hydroxylamine(O-α-L-Fucopyranosylhydroxylamine) (4) | 380 |
| O-(6-Deoxy-β-L-Galactopyranosyl)Hydroxylamine(O-β-L-Fucopyranosylhydroxylamine) (5) | 380 |
| Acknowledgments | 381 |
| References | 385 |
43. | Functionalization of Terminal Positions of Sucrose---Part I: Synthesis of 2,3,3',4,4'-Penta-O-Benzylsucrose and Differentiation of the Terminal Positions (1,6,6') / S. Jarosz | 387 |
| Experimental Methods | 389 |
| General Methods | 389 |
| 1',6,6'-Tri-O-Tritylsucrose (2) | 390 |
| 2,3,3',4,4'-Penta-O-Benzyl-1',6,6'-Tri-O-TrityIsucrose (3) | 391 |
| 2,3,3',4,4'-Penta-O-Benzylsucrose (4) | 391 |
| 2,3,3',4,4'-Penta-O-Benzyl-6,6'-Di-O-p-Nitrobenzoylsucrose (5) | 392 |
| 2,3,3'4,4'-Penta-O-Benzyl-1'-O-Benzyloxymethyl-6,6'-Di-O-p-Nitrobenzoylsucrose (6) | 392 |
| 2,3,3',4,4'-Penta-O-Benzyl-1'-O-Benzyloxymethylsucrose (7) | 392 |
| 2,3,3',4,4'-Penta-O-Benzyl-1'-O-Benzyloxymethyl-6'-O-Tert-Butyldiphenylsilylsucrose (8) | 393 |
| Carbohydradte Chemistry: Proven Synthetic Methods | |
| 1'-O-Benzyloxymethyl-6,6'-Di-O-Tert-Butyldiphenylsilyl-2,3,3'4,4'-Penta-O-Benzylsucrose (9) | 393 |
| 2,3,3',4,4'-Penta-O-Benzyl-1'-O-Benzyloxymethyl-6-O-Tert-Butyldiphenylsilylsucrose (10) | 394 |
| References | 411 |
44. | Functionalization of Terminal Positions of Sucrose---Part II: Preparation of 1',2,3,3',4,4'-Hexa-O-Benzylsucrose and 6,6'-Bis-O-(2-Hydroxyethyl)-1',2,3,3',4,4'-Hexa-O-Benzylsucrose / S. Jarosz | 413 |
| Experimental Methods | 414 |
| General Methods | 414 |
| 6,6'-Di-O-Tritylsucrose (1) | 416 |
| 1',2,3,3',4,4'-Hexa-O-Acetyl-6,6'-Di-O-Tritylsucrose (1A) | 417 |
| 1',2,3,3',4,4'-Hexa-O-Benzyl-6,6'-Di-O-Tritylsucrose (2) | 417 |
| 1',2,3,3',4,4'-Hexa-O-Benzyl-6,6'-Dichloro-6,6'-Dideoxysucrose (3A) | 418 |
| 6,6'-Di-O-Acetyl-1',2,3,3',4,4'-Hexa-O-Benzylsucrose (4) | 418 |
| 1',2,3,3',4,4'-Hexa-O-Benzylsucrose (5) | 419 |
| 6,6'-Di-O-Allyl-1',2,3,3',4,4'-Hexa-O-Benzylsucrose (6) | 419 |
| 1',2,3,3',4,4'-Hexa-O-Benzyl-6,6'-Bis-(O-Tert-Butoxycarbonylmethylsucrose (7) | 420 |
| 1',2,3,3',4,4'-Hexa-O-Benzyl-6,6'-Bis-(O-2-Hydroxyethyl) Sucrose (8) | 420 |
| References | 430 |
| Index | 431 |