134403-89-7Relevant academic research and scientific papers
A synthetic procedure for the preparation of oligonucleotides without using ammonia and its application for the synthesis of oligonucleotides containing O-4-alkyl thymidines
Eritja,Robles,Avino,Albericio,Pedroso
, p. 4171 - 4182 (2007/10/02)
The preparation of 5'-O-dimethoxytrityl (DMT) and p-nitrophenylethyl (NPEOC, NPE) protected nucleosides linked to 4-(2-hydroxyethyl)-3-nitrobenzoic acid derivatives is described. These products attached to controlled-pore glass supports and together with
NPE-resin, a new approach to the solid-phase synthesis of protected peptides and oligonucleotides I: Synthesis of the supports and their application to oligonucleotide synthesis
Eritja,Robles,Fernandez-Forner,Albericio,Giralt,Pedroso
, p. 1511 - 1514 (2007/10/02)
The preparation of polymeric supports containing a base labile 2-(2-nitrophenyl) ethyl linkage and the attachment of protected nucleosides is described together with their application to oligonucleotide synthesis.
Nucleotide. XIV. Substituierte β-Phenylaethyl-Gruppen. Neue Schutzgruppen fuer Oligonucleotid-Synthesen nach dem Phosphorsaeuretriester-Verfahren
Uhlmann, Eugen,Pfleiderer, Wolfgang
, p. 1688 - 1703 (2007/10/02)
Various o- and p-substituted β-phenylethanols (2-10) have been synthesized and investigated as blocking groups in the phosphotriester approach.A large number of 5'-O-tritylated thymidine-3'-phosphotriesters (13-36) with two different phosphate protecting groups have been prepared, characterized, and studied according to their chemical stability and usefullness for oligonucleotide syntheses.The combination of a 5'-O-monomethoxytrityl- and a 3'-(2,5-dichlorophenyl, p-nitrophenylethyl)-phosphate function as in 18 turned out to possess optimal properties as a monomeric nucleotide building block due to the fact that these blocking groups can be quantitatively and selectively be removed without harming each other by trifluoroacetic acid in chloroform to 41, by oximate to 42, and by DBU to 43.The base-catalyzed removal of the monosubstituted phenylethyl groups by DBU or DBN respectively as well as the disubstituted phenylethyl groups by triethylamine in aprotic solvents is a β-elimination process leading to phosphodiesters without attack on the P-center.
