154738-07-5Relevant articles and documents
Synthesis and Properties of N-Tritylthio Nucleoside Derivatives and Reductive Removal of the Tritylthio Group by Use of Tributyltin Hydride and Tris(trimethylsilyl)silane
Sekine, Mitsuo,Seio, Kohji
, p. 3087 - 3094 (2007/10/02)
N-Sulfenylations of ribo- and deoxyribo-nucleoside derivatives have been studied by the use of triphenylmethanesulfenyl chloride as a sulfenylating reagent under a variety of conditions.A two-phase system using 0.2 mol dm-3 Na2CO3-CH2Cl2 was found to be effective for N-sulfenylation of deoxycytidine, deoxyadenosine and guanosine derivatives (7b, 9b, 9c and 11d), which were partially or fully protected at the hydroxy functions.In the case of adenosine 9c, the N1-sulfenylated deoxyadenosine derivative 10f was also formed.For the N-sulfenylation of the 5'-protected thymidine derivative 7a, phase-transfer catalysis was successfully used.It was found that the N-TrS group could be removed by reductive C-S bond cleavage using Bu3SnH or (Me3Si)3SiH in toluene in the presence of AIBN under reflux for 5 min.In several cases, the Bu3SnH-mediated deprotection occurred in the absence of AIBN.When triethylborane or sonication was used as a radical initiator, the cleavage reaction could be carried out at room temperature.The stability of the TrS group attached to these nucleoside bases was examined under several acidic and basic conditions.
