Synthesis and reactivity of nucleoside sulfilimines

Article abstract of DOI:10.1080/10426500490257113

Treatment of 3′- and 5′-protected deoxycytidine and deoxyadenosine with bis-[α,α-bis(trifluoromethyl)benzyloxy] diphenylsulfur resulted in the formation of the corresponding 4-N- and 6-N-diphenylsulfilimine derivatives in good yields. The 4-N- and the 6-N-dimethylsulfilimines of these nucleosides were obtained using DMSO / trifluoroacetic anhydride. These dimethyl- and diphenylsulfilimine derivatives were found to have characteristic UV absorbances at 284-296 nm. Stability tests of the nucleoside dimethylsulfilimine and diphenylsulfilimine under the conditions commonly used in oligonuclotide chemistry by the H-phosphonate approach were executed, and possible applications of these compounds have been discussed.