Synthesis of 1′‐Homo‐N‐nucleosides from Hexitols.

Abstract

Nucleic acids Nucleic acids U 0700Synthesis of 1'-Homo-N-nucleosides from Hexitols. -A new route to the synthesis of title homo-N-nucleosides (IV) and (VIII) is presented, involving the highly stereoselective nucleophilic epoxide opening of bisepoxides (II) and (VI), resp., with silylated nucleobases in the presence of Mg(ClO4)2 and subsequent O-heterocyclization as key step. -(SALADINO*, R.; CIAMBECCHINI, U.; HANESSIAN, S.; Eur. J. Org.

Enantioselective Synthesis of Homo-N-Nucleosides Containing a 1,4-Dioxane Sugar Analog

“…There has been an increasing interest in the synthesis of nucleoside analogs with modifications of the sugar moiety for the purpose of obtaining new antiviral and antitumor agents [ 1 , 2 , 3 ]. A well known class of modified nucleosides are the homo- N- and C -glycosidic nucleosides [ 4 , 5 , 6 , 7 , 8 ] The insertion of a methylene group between the heterocyclic base and the sugar moiety results in a more flexible structure, and due to the lack of an anomeric acetal position, these nucleosides are in general resistant to enzymatic degradation [ 8 ]. For these reasons, we decided to pursue the synthesis of nucleoside analogs, however, based on the conformationally more flexible, optically active homo-1,4-dioxane sugar analogs.…”