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
Tabella dei contenuti
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
Circa l’autore
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, Shanghai Tech University, China. His research interests focus on organic synthesis, asymmetric catalysis, carbohydrate chemistry and chemical biology.
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