322732-66-1Relevant articles and documents
β-Heteroarylethyl Groups - New Phosphate-Protecting Groups for Phosphotriester Chemistry
Reiner, Tilman,Kvasyuk, Evgeny,Pfleiderer, Wolfgang
, p. 3053 - 3063 (2007/10/03)
The β-heteroaryl-substituted ethanols 6-10 were synthesized and, together with pyridine-2-ethanols and pyridine-4-ethanols, were tested as a new type of phosphate-protecting groups in the synthesis of oligonucleotides by the phosphotriester approach. The synthesis of 5'-O-(monomethoxytrityl)thymidine 3'-(β-heteroarylethyl 2,5-dichlorophenyl phosphates) 13-17 and 21 provided useful monomeric building blocks in which the various blocking groups could be removed selectively by acid (MeOTr), oximate (2,5-dichlorophenyl phosphate), and 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU) (heteroarylethyl phosphate) treatment. The new, fully blocked dimers 38-41, with β-heteroarylethyl protecting groups in the phosphate moiety, were synthesized. The β-heteroarylethyl groups show a broad range of stability towards base treatment in aprotic solvents depending upon the activation of the H-C(β) atoms by the heterocyclic moiety.
