Synthesis of phosphorofluoridates and phosphorofluoridothioates via the phosphoramidite approach.
We present a very efficient synthetic procedure leading to the phosphorofluoridates RO-P(O)(OH)F 1 or phosphorofluoridothioates RO-P(S)(OH)F 2, which is based on the intermediary of fluorophosphoramidites (RO)P(F)N(i)Pr2 5 [R = 9-(hydroxyethyloxymethyl)guaninyl), 3'azido-3'deoxythymidinyl, thymidinyl, anhydrothymidinyl, cholesteryl, N6-benzoyl-5'-O-(4,4'-dimethoxytrityl)-2'-deoxyadenosinyl]. The activation of the amino group was performed with trimethylchlorosilane (TMCS).
Dabkowski
Wojciech
W
Centre of Molecular and Macromolecular Studies, Polish Academy of Sciences, 90-363, Łódź, Sienkiewicza 112, Poland. wdabkow@bilbo.cbmm.lodz.pl
Tworowska
Izabela
I
D005459:Fluorides / Q000737:chemistry; D005461:Fluorine / Q000737:chemistry; D017611:Fluorine Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D009943:Organophosphorus Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D010710:Phosphates / Q000737:chemistry; D013457:Sulfur Compounds / Q000138:chemical synthesis* / Q000737:chemistry
D017611:Fluorine Compounds; D009943:Organophosphorus Compounds; D010710:Phosphates; D013457:Sulfur Compounds; C434331:phosphoramidite; C012980:fluorophosphate; D005461:Fluorine; D005459:Fluorides