De Novo Synthesis of 4‘-Ethoxy Nucleoside Analogues

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...

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Veröffentlicht in:	Journal of organic chemistry 2002-11, Vol.67 (22), p.7649-7655
Hauptverfasser:	Hegedus, Louis S, Geisler, Lisa, Riches, Andrew G, Salman, Sarri S, Umbricht, Gisela
Format:	Artikel
Sprache:	eng
Schlagworte:	4-Butyrolactone - analogs & derivatives Carbohydrates. Nucleosides and nucleotides Chemistry Exact sciences and technology Furans - chemistry Hydroxylation Molecular Structure Nucleosides - chemical synthesis Nucleosides - chemistry Nucleosides, nucleotides and oligonucleotides Organic chemistry Preparations and properties Stereoisomerism
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Zusammenfassung:	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.
ISSN:	0022-3263 1520-6904
DOI:	10.1021/jo020151f