57019-73-5Relevant academic research and scientific papers
Studies of nucleosides and nucleotides LX. Purine cyclonucleosides 24. Cleavage of S anhydro linkage of cyclonucleosides by intramolecular rearrangement
Ikehara,Ogiso
, p. 121 - 131 (2007/10/09)
8,3' S Cycloadenosine was tosylated at 5' OH to give compound 2. When compound 2 was treated with NaSH, two products, 8,3' anhydro 9 (5' deoxy 5' mercapto β D xylofuranosyl)adenine and 8 mercapto 9 (3',5' di deoxy 3',5' dimercapto β D xylofuranosyl)adenine were obtained in a ratio of 6:4. A mechanism involving sulfonium intermediate was proposed. Thus it was proved that S anhydro linkage of adenine cyclonucleosides could be cleaved rather easily by the intramolecular attack of neighboring SH groups.
