Nucleotides, Part LXVI <FN ID="fnss">Part LXV: [1].</FN>, β-Heteroarylethyl Groups New Phosphate-Protecting Groups for Phosphotriester Chemistry
In: Helvetica Chimica Acta, Jg. 83 (2000-11-08), Heft 11, S. 3053-3063
Online
serialPeriodical
Zugriff:
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.
Titel: |
Nucleotides, Part LXVI <FN ID="fnss">Part LXV: [1].</FN>, β-Heteroarylethyl Groups New Phosphate-Protecting Groups for Phosphotriester Chemistry
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Autor/in / Beteiligte Person: | Reiner, Tilman ; Kvasyuk, Evgeny ; Pfleiderer, Wolfgang |
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Zeitschrift: | Helvetica Chimica Acta, Jg. 83 (2000-11-08), Heft 11, S. 3053-3063 |
Veröffentlichung: | 2000 |
Medientyp: | serialPeriodical |
ISSN: | 0018-019X (print) ; 1522-2675 (print) |
DOI: | 10.1002/1522-2675(20001108)83:11<3053::AID-HLCA3053>3.0.CO;2-X |
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