Alvarez de Cienfuegos, Luis; Mota, Antonio J.; Rodriguez, Concepcion; Robles, Rafael published an article on January 17 ,2005. The article was titled 《Highly efficient synthesis of 2′,3′-didehydro-2′,3′-dideoxy-β-nucleosides through a sulfur-mediated reductive 2′,3′-trans-elimination. From iodomethylcyclopropanes to thiirane analogs》, and you may find the article in Tetrahedron Letters.Electric Literature of C17H16N2O5 The information in the text is summarized as follows:
Taking into account the thiophilic properties of iodine, a very simple methodol. to achieve 2′,3′-didehydro-2′,3′-dideoxy-β-nucleosides in high yield was performed, using mild, and inexpensive conditions, by means of the treatment of 2′-deoxy-3′,5′-dibenzoyl-2′-iodo-β-nucleoside derivatives with NaHS. The process has shown to be highly dependent of the relative geometry between the iodine atom and the adjacent leaving group. In this way, different essays carried out with pyranose derivatives have concluded in no reaction when the vicinal groups to eliminate do not adopt a trans-diaxial disposition. In addition, the treatment of 2-iodomethyl-cyclopropane-1,1-dicarboxylic acid di-Et ester under the same conditions softly and readily leads to the obtention of a mixture of the expected 2-allyl-malonic acid di-Et ester (as the minor product) and the thiirane derivative 2-thiiranylmethyl-malonic acid di-Et ester (as the major product). In this case, the responsible of the reaction progress are the nucleophilic properties of the sulfur atom rather than the thiophilic character of the iodine atom. The results came from multiple reactions, including the reaction of ((2S,5R)-5-(5-Methyl-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)-2,5-dihydrofuran-2-yl)methyl benzoate(cas: 122567-97-9Electric Literature of C17H16N2O5)
((2S,5R)-5-(5-Methyl-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)-2,5-dihydrofuran-2-yl)methyl benzoate(cas: 122567-97-9) belongs to pyrimidine. Pyrimidine nucleotide derivatives have a wide range of biological applications. For example, pyrimidine derivatives are useful in DNA repair studies involving cancer and epigenetics.Electric Literature of C17H16N2O5
Referemce:
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia