Isoxazolidine analogs of nucleosides

Stereochemistry of cycloaddition of (S)-N-(1-phenylethyl)-C-diethoxyphosphorylated nitrone with vinyl acetate. Studies on mutarotation of 3-(O,O-diethylphosphoryl)-5-hydroxyisoxazolidines

“…1). Several achiral as well as chiral nitrones have been examined in the reaction with vinyl acetate including synthetic, [7][8][9][10][11][12][13][14][15][16][17][18][19][20][21] as well as theoretical studies. 15,22 Since 5-acetoxyisoxazolidines could be used as starting materials in the Vorbrü ggen reaction, 23 the synthesis of isoxazolidine analogues of nucleosides became apparent.…”

Modified nucleosides from nitrones: a new and efficient stereoselective approach to isoxazolidinyl thymidine derivatives

“…3 Also, nucleosides 2 and 3 containing an isoxazolidine moiety have been described to have promising therapeutic utility in the development of anti-AIDS agents. 4 As a consequence, syntheses of isoxazolidinyl nucleosides of type 2 and 3 have been recently reported. 5,6 Recent investigations in this laboratory have revealed that chiral a-alkoxy and a-amino nitrones serve as versatile chiral building blocks in the preparation of several naturally occurring nitrogen-containing compounds.…”

Novel Isoxazolidine and γ-Lactam Analogues of Homonucleosides

“…Incorporation of the isoxazolidine ring into a nucleoside framework as a sugar part replacer was first proposed by Tronchet and co-workers [24,25] with the intention to study antiviral [20,26,27,28,29,30,31], antibacterial [32] and antifungal [33] activities of the compounds. Other research groups then intensively explored this field further.…”