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De Novo Synthesis of 4‘-Ethoxy Nucleoside Analogues

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journal contribution
posted on 27.09.2002, 00:00 by Louis S. Hegedus, Lisa Geisler, Andrew G. Riches, Sarri S. Salman, Gisela Umbricht
Butenolides 5a and 13 were used as optically active templates in the de novo synthesis of 4‘-disubstituted nucleoside analogues. The butenolides were reduced and acylated in situ to give acetates 10 and 14. Vorbrüggen coupling gave the protected nucleoside analogues 11 and 15. Reduction of 11 gave 4‘-ethoxy-2‘,3‘-dideoxythymidine (6) and deprotection of 15 gave 4‘-ethoxy-2‘,3‘-dideoxydidehydrothymidine (7). The cis-dihydroxylation of a variety of butenolides occurred with the major product formed from oxidation of the β-face.

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