441019-90-5Relevant academic research and scientific papers
De novo synthesis of 4′-ethoxy nucleoside analogues
Hegedus, Louis S.,Geisler, Lisa,Riches, Andrew G.,Salman, Sarri S.,Umbricht, Gisela
, p. 7649 - 7655 (2007/10/03)
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. Vorbrueggen 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.
Asymmetric synthesis of 4′-ethoxy-2′,3′-didehydro-2′, 3′-dideoxynucleosides by palladium-catalyzed kinetic discrimination between the corresponding diastereoisomeric lactol acetates
Hegedus, Louis S.,Hervert, Katherine L.,Matsui, Satoshi
, p. 4076 - 4080 (2007/10/03)
4′-Substituted nucleoside analogues have been synthesized using palladium-catalyzed asymmetric allylic amination conditions. A kinetic discrimination between the diastereomeric lactol acetates (3) produced the desired aminated products (6a-d) and recovered acetate (α-3) in high yields and 97:3 diastereoselectivity. Epimerization of the recovered lactol acetate (α-3) produced a 60:40 α/β mixture of (3), which could be resubjected, in principle, to the palladium-catalyzed asymmetric allylic amination conditions.
