77594-22-0Relevant academic research and scientific papers
Thio-sugars. Part 6. Seco-nucleosides related to 4-thio-DL-erythrofuranose and 4-thio-DL-ribofuranose.
McCormick, Joan E.,McElhinney, R. Stanley
, p. 256 - 281 (2007/10/02)
The thio-sugar synthesis has been adapted to prepare seco-nucleosides, so named by analogy with steroids, for comparison with antiviral agents such as acycloguanosine.Bis(β-hydroxyethyl) sulphoxide gave, via a triacetate, crystalline 4'-thio-2',3'-seco-3'-norcytidine and similar nucleosides - also obtainable by successive action of NaIO4 and NaBH4 on the corresponding (much less soluble) 4-thioerythrosides.In unsymmetrical methyl sulphoxides, the presence of β-OH groups tends to reverse the direction of normal Pummerer rearrangement and both 1',2'-seco-2'-nor and 2',3'-dinoruridines were thus inaccessible: the latter have the acycloguanosine type side-chain.However, 2',3'-seco-3',5'-dinoruridines were readily isolated and in turn yielded 2,2'-but not 2',6-cyclonucleosides.The scope of these uridine cyclisations is briefly reviewed.
