Carbohydrate Chemistry in the Total Synthesis of Naturally Occurring Glycosides
Revolutionize your manufacturing processes and more with this groundbreaking introduction
Carbohydrates and complex glycosides are important classes of molecules. The ubiquitous glycosides are extremely diverse in structure and functions, and many of them are of pharmacological significance. Purification of a homogeneous glycoside from the nature sources, especially in an appreciable amount, is always difficult. Chemical synthesis provides a feasible access to the homogenous glycosides and their congeners.
Carbohydrate Chemistry in the Total Synthesis of Naturally Occurring Glycosides presents about 10 families of naturally occurring glycoside natural products, including about 150 molecules that organic chemists have devoted a lot of effort toward their synthesis. In each example, the background of each natural glycoside, including its natural resources, its isolation process and its bioactivities have been described; the total synthesis of the natural glycoside is presented with special emphasis on the glycosylation reaction, the strategy on saccharides assembly, the protecting group manipulation, and the method for the synthesis of the rare saccharide units. Readers can clearly see the progress of total synthesis of naturally occurring glycosides, from early to current arts, from simple to complex molecules, and from tedious strategy to highly efficient and economical methodologies in this book. It will highly benefit the further developments in the total synthesis of naturally occurring glycosides and synthetic carbohydrate chemistry.
Carbohydrate Chemistry in the Total Synthesis of Naturally Occurring Glycosides is ideal for Organic Chemists, Biochemists, Pharmaceutical and Medicinal Chemists, Natural Products Chemists, and Pharmaceutical Industry
Preface xi List of Abbreviations xiii 1 Introduction 1 References 5 2 Aromatic Polyketide Glycosides 7 Landomycin A 7 Olivomycin A 13 Ciclamycin 17 Vineomycin B2 20 Trioxacarcin 25 Daunorubicin 29 Aquayamycin 30 Vineomycin A1 30 Derhodinosylurdamycin A 31 Jadomycins 31 Tan-1085 33 Benanomicins and Pradimicins 33 Pluramycins 34 Marmycins 35 Cassialoin 36 FD-594 36 Calixanthomycin A 38 Lactonamycin 38 Lomaiviticin A(−) 39 References 42 3 Enediyne Glycosides 47 Calicheamicin γI1 48 Namenamicin 54 Shishijimicin A 56 Neocarzinostatin Chromophore 58 Maduropeptin Chromophore 59 References 61 4 Flavonoid Glycosides 63 Flavonol 3-O-glycosides 65 Quercetin 3-sophorotrioside 65 Sl0101 66 Flavone and Isoflavone 7-O-Glycosides 67 A-76202 67 Flavonol 3-O- and 7-O-Bisglycosides 70 Kaempferitrin 70 Flavonol 5-O-Glycosides 71 Camellianin B 71 Flavone 6-C-Glycosides 72 Chafurosides 72 Cyanidin 3-O-Glycosides 74 Cyanidin 3-O-β-D-glucoside 74 Other Examples 75 Quercetin 3-O-β-D-Glucuronide 75 Quercetin 3-O-(2 ′′-Galloyl)-α-L-arabinopyranoside 75 Isoquercitrin Coumarate 75 Kaempferol 3-O-(3 ′′,6′′-di-O-E-p-coumaroyl)-β-D-Glucopyranoside 76 Platanoside 76 Quercetin-3-O-trisaccharide 79 78 Houttuynoid A 78 Daidzin, Genistin, Ononin, and Sissotrin 78 Apigenin 7-O-Cellobioside 79 Suttellarin 80 Calabricoside A 80 Kaempferol-3-O-7-O-bisglycoside 88 81 Vicenines 81 Carambolaflavone A 83 Flavocommeline 83 Schaftoside 84 Pelargonidin 3-O-6′′-O-acetyl-β-D-glucopyranoside 85 Cyanidin 4′-O-methyl-3-O-glucoside 86 References 86 5 Macrolide Glycosides 89 Erythromycin 89 Apoptolidin A 94 Spinosyn A (Lepicidin A) 98 Tiacumicin B 103 Pikromycin 106 Polycavernoside A 106 Auriside A 107 Lyngbyaloside B 108 Avermectin 109 Formamicin 109 Tylosin 109 Mangrolide 112 Amphotericin B 113 Aldgamycins 113 Mycinamicin IV 114 References 115 6 Nucleosides 119 Tunicamycin 119 Hikizimycin 126 Herbicidins 128 A201A 131 Amipurimycin 134 Caprazamycin 137 Polyoxin J 141 Octosyl Acid A 142 HF-7 143 Malayamycin 143 Capuramycin 144 Muraymycin 144 Plicacetin, Streptcytosine A, and Amicetin 145 A-94964 146 Miharamycin B 148 References 149 7 Peptide Glycosides 153 Vancomycin 155 Bleomycin A2 159 Mannopeptimycin 165 Syndecan 170 Lipoglycopeptide Arylomycin 171 References 172 8 Resin Glycosides 175 Calonyctin A 176 Tricolorin 179 Ipomoeassin 185 Woodrosin I 189 Batatosides l 191 Batatin VI 191 Merremoside d 192 Murucoidins 192 References 195 9 Steroid Glycosides 197 Cholestane Type Steroid Glycosides 197 OSW-1 197 Periploside A 201 Luzonicosides and Sepositoside 204 Cardenolide Type Steroid Glycosides 207 Digitoxin 207 Furostane Type Steroid Glycosides 212 Furostan Saponin and Methyl Protodioscin 212 Spirostan Type Steroid Glycosides 214 Desgalactotigonin 214 Forbeside E 216 Osladin 216 Pavonimin 218 Dioscin 218 Polyphyllin D 219 Maidong Saponin C 220 Xiebai Saponin I 221 Candicanoside A 222 Ouabain 222 Timosaponin BII 223 Solamargine 223 Rhodexins 225 Goniopectenoside B 226 Astrosterioside A 226 Linckoside 227 Trewianin 228 P57 228 Oleandrin 230 References 231 10 Triterpenoid Glycosides 233 Ciwujianoside C3 233 QS-21 234 Lobatoside E 238 Ginsenosides 239 Echinoside A 242 Anemoclemoside B 245 Betavugaroside III 247 Δ20-Ginsenosides 247 Flaccidoside II 248 Asiaticoside 249 Pulsatilla Saponin D 249 Lotoidoside D 250 Astragalosides 252 Chikusetsu Saponins 253 References 253 11 Miscellaneous Glycosides 257 Allosamidin 257 Staurosporine 257 Everninomicin 13,384-1 259 Brasilicardins 263 Efrotomycin 266 Peyssonoside A 267 Amycolamicin/Kibdelomycin 268 Strictosidine-Type Indole Alkaloid Glycosides 268 Cotylenin A 270 Pyrolaside B 271 References 273 Index 275
Biao Yu is Professor and currently Director of State Key Laboratory of Bioorganic and Natural Products Chemistry at Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences. He was given the Humboldt Research Award from the Alexander von Humboldt Foundation in 2020, the Roy L. Whistler Award from the International Carbohydrate Organization in 2022, and was elected as the Academician of the Chinese Academy of Sciences in 2021. He has spent nearly 30 years working on carbohydrate chemistry, especially the total synthesis of naturally occurring glycosides. Xiaoyu Yang is Associate Professor at the School of Physical Science and Technology, ShanghaiTech University, China. His research interests focus on organic synthesis, asymmetric catalysis, carbohydrate chemistry and chemical biology.
