Practical synthesis of 2'-deoxy-4'-thioribonucleosides: substrates for the synthesis of 4'-thioDNA.
We report herein a practical synthesis of 4'-thiothymidine (15) and appropriately protected 2'-deoxy-4'-thiocytidine (16), -thioadenosine (27), and -thioguanosine (29) derivatives, substrates for the synthesis of 4'-thioDNA, from the corresponding 4'-thioribonucleosides. 2'-deoxy-4'-thiopyrimidine nucleosides were synthesized using a radical reaction of the corresponding 2'-alpha-bromo derivatives, which were prepared via 2,2'-O-anhydro derivatives. 2'-deoxy-4'-thiopurine nucleosides were synthesized using the same radical reaction of the corresponding 2'-beta-bromo derivatives.
Inoue
Naonori
N
Graduate School of Pharmaceutical Sciences, Hokkaido University, Kita-ku, Sapporo 060-0812, Japan.
Kaga
Daisuke
D
Minakawa
Noriaki
N
Matsuda
Akira
A
D004247:DNA / Q000737:chemistry*; D015394:Molecular Structure; D012263:Ribonucleosides / Q000737:chemistry*; D013872:Thionucleosides / Q000138:chemical synthesis* / Q000737:chemistry*
D012263:Ribonucleosides; D013872:Thionucleosides; D004247:DNA