Carbohydrate Chemistry in the Total Synthesis of Naturally Occurring Glycosides

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. Cover Half Title Carbohydrate Chemistry in the Total Synthesis of Naturally Occurring Glycosides Copyright Contents Preface List of Abbreviations 1. Introduction References 2. Aromatic Polyketide Glycosides Landomycin A Olivomycin A Ciclamycin Vineomycin B2 Trioxacarcin Daunorubicin Aquayamycin Vineomycin A1 Derhodinosylurdamycin A Jadomycins Tan‐1085 Benanomicins and Pradimicins Pluramycins Marmycins Cassialoin FD‐594 Calixanthomycin A Lactonamycin Lomaiviticin A(−) References 3. Enediyne Glycosides Calicheamicin γ1I Namenamicin Shishijimicin A Neocarzinostatin Chromophore Maduropeptin Chromophore References 4. Flavonoid Glycosides Flavonol 3‐O‐glycosides Quercetin 3‐sophorotrioside SL0101 Flavone and Isoflavone 7‐O‐Glycosides A‐76202 Flavonol 3‐O‐ and 7‐O‐Bisglycosides Kaempferitrin Flavonol 5‐O‐Glycosides Camellianin B Flavone 6‐C‐Glycosides Chafurosides Cyanidin 3‐O‐Glycosides Cyanidin 3‐O‐β‐d‐glucoside Other Examples Quercetin 3‐O‐β‐d‐Glucuronide Quercetin 3‐O‐(2′′‐Galloyl)‐α‐l‐arabinopyranoside Isoquercitrin Coumarate Kaempferol 3‐O‐(3′′,6′′‐di‐O‐E‐p‐coumaroyl)‐β‐d‐Glucopyranoside Platanoside Quercetin‐3‐O‐trisaccharide 79 Houttuynoid A Daidzin, Genistin, Ononin, and Sissotrin Apigenin 7‐O‐Cellobioside Suttellarin Calabricoside A Kaempferol‐3‐O‐7‐O‐bisglycoside 88 Vicenines Carambolaflavone A Flavocommeline Schaftoside Pelargonidin 3‐O‐6′′‐O‐acetyl‐β‐d‐glucopyranoside Cyanidin 4′‐O‐methyl‐3‐O‐glucoside References 5. Macrolide Glycosides Erythromycin Apoptolidin A Spinosyn A (Lepicidin A) Tiacumicin B Pikromycin Polycavernoside A Auriside A Lyngbyaloside B Avermectin Formamicin Tylosin Mangrolide Amphotericin B Aldgamycins Mycinamicin IV References 6. Nucleosides Tunicamycin Hikizimycin Herbicidins A201A Amipurimycin Caprazamycin Polyoxin J Octosyl Acid A HF‐7 Malayamycin Capuramycin Muraymycin Plicacetin, Streptcytosine A, and Amicetin A‐94964 Miharamycin B References 7. Peptide Glycosides Vancomycin Bleomycin A2 Mannopeptimycin Syndecan Lipoglycopeptide Arylomycin References 8. Resin Glycosides Calonyctin A Tricolorin Ipomoeassin Woodrosin I Batatosides L Batatin VI Merremoside D Murucoidins References 9. Steroid Glycosides Cholestane Type Steroid Glycosides OSW‐1 Periploside A Luzonicosides and Sepositoside Cardenolide Type Steroid Glycosides Digitoxin Furostane Type Steroid Glycosides Furostan Saponin and Methyl Protodioscin Spirostan Type Steroid Glycosides Desgalactotigonin Forbeside E Osladin Pavonimin Dioscin Polyphyllin D Maidong Saponin C Xiebai Saponin I Candicanoside A Ouabain Timosaponin BII Solamargine Rhodexins Goniopectenoside B Astrosterioside A Linckoside Trewianin P57 Oleandrin References 10. Triterpenoid Glycosides Ciwujianoside C3 QS‐21 Lobatoside E Ginsenosides Echinoside A Anemoclemoside B Betavugaroside III Δ20‐Ginsenosides Flaccidoside II Asiaticoside Pulsatilla Saponin D Lotoidoside D Astragalosides Chikusetsu Saponins References 11. Miscellaneous Glycosides Allosamidin Staurosporine Everninomicin 13,384‐1 Brasilicardins Efrotomycin Peyssonoside A Amycolamicin/Kibdelomycin Strictosidine‐Type Indole Alkaloid Glycosides Cotylenin A Pyrolaside B References Index