2004
DOI: 10.1002/chin.200412211
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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.

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“…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.…”
Section: Introductionmentioning
confidence: 99%
“…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.…”
Section: Introductionmentioning
confidence: 99%