1132807-45-4Relevant academic research and scientific papers
Additive pummerer reaction of 3,5-O-(Di-tert-butyl)silylene-4-thiofuranoid glycal: A high-yield and β-selective entry to 4-thioribonucleosides
Haraguchi, Kazuhiro,Matsui, Hiromitsu,Takami, Shin,Tanaka, Hiromichi
, p. 2616 - 2619 (2009)
Upon reacting 3,5-O-(di-tert-butyl)silylene-4-thiofuranoid glycal S-oxide (6) with Ac2O/TMSOAc/BF3·OEt2 in CH 2Cl2, the additive Pummerer reaction proceeded to furnish the corresponding 1,2-di-O-acetyl-4-thioribofuranose 7. Compound 7 serves as a highly β-selective glycosyl donor in the Vorbrueggen condensation carried out in the presence of TMSOTf. Thus, the 4-thio-β-D-ribofuranosyl derivatives of uracil, thymine, N4-acetylcytosine, 6-chloropurine, and 2-amino-6-chloropurine were synthesized. The use of 7 can be extended to the β-selectivesynthesis of 4-thio-C-ribonucleosides.
