Oligosaccharides through reactivity tuning: convergent synthesis of the trisaccharides of the steroid glycoside Sokodoside B isolated from marine sponge Erylus placenta |
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Authors: | Somnath Dasgupta Balaram Mukhopadhyay |
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Affiliation: | a Medicinal and Process Chemistry Division, Central Drug Research Institute, Chattar Manzil Palace, Lucknow 226001, Uttar Pradesh, India b Department of Chemistry, Inorganic Chemistry Section, Jadavpur University, Jadavpur, Kolkata 700032, West Bengal, India |
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Abstract: | Chemical synthesis of the trisaccharide of the steroid glycoside Sokodoside B isolated from Erylus placenta is reported. Stereoselective, high-yielding glycosylation strategies through thioglycoside activation using H2SO4 immobilized on silica in conjunction with N-iodosuccinimide are used for better results. A late stage TEMPO-mediated oxidation was performed for the formation of required uronic acid moiety. An analog of the target trisaccharide is also prepared by using a bis-glycosylation approach. |
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