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Studies on the synthesis of steroid glycosides of deoxy sugar



Studies on the synthesis of steroid glycosides of deoxy sugar



Liebigs Annalen der Chemie (11): 2135-2150



The 2-deoxy-2-iodo-.alpha.-glycosides 3, 4, 5, and 9 are obtained stereoselectively by condensation of cholesterin and digitoxigenin with the glycals 1, 2, and 8 in the presence of N-iodosuccinimide. In a concomitant side reaction the formation of the direct N-iodosuccinimide adducts like e.g. 6 is observed. Similar treatment of 11 in butanone only partially leads to the expected glycosides 12 or 13 but rather to the formation of the hex-2-enopyranosides 17 or 18. The latter can also be obtained by a Ferrier rearrangement and their structures are assured by spectroscopy and by hydrogenation (to 20). Following hydrogenolytic deiodination the cardenolide glycosides 10, 14, and 15 are obtained. Acid-catalyzed glycosylation of triacetyldigitoxose 21 with digitoxigenin yields the .alpha.- and .beta.-anomers 10 and 25 in a maximum yield of 50% and a ratio of approximately 2:3. At elevated temperatures the relative amount of the .beta.-component 25 increases with, however, heavily decreasing yields. Glycosylation of acetobromodigitoxose 22 using various silver salt promoters similarly gives approximately 50% yield and a ratio of .alpha.:.beta. = 2:3.

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