132625-21-9Relevant articles and documents
Tricyclanos: Conformationally constrained nucleoside analogues with a new heterotricycle obtained from a d-ribofuranose unit
Kicsák, Máté,Mándi, Attila,Varga, Szabolcs,Herczeg, Mihály,Batta, Gyula,Bényei, Attila,Borbás, Anikó,Herczegh, Pál
supporting information, p. 393 - 401 (2018/02/06)
A novel type of nucleoside analogue in which the sugar part is replaced by a new tricycle, 3,7,10-trioxa-11-azatricyclo[5.3.1.05,11]undecane has been prepared by substrate-controlled asymmetric synthesis. 1,5-Dialdehydes obtained from properly protected or unprotected uridine, ribothymidine, cytidine, inosine, adenosine and guanosine by metaperiodate oxidation reacted readily with tris(hydroxymethyl)aminomethane to provide the corresponding tricyclic derivatives with three new stereogenic centers. Through a double cyclisation cascade process the tricyclic compounds were obtained in good to high yields, with very high diastereoselectivity. Formation of one stereoisomer, out of the eight possible, was observed in all cases. The absolute configuration of the new stereotriad-containing tricyclic systems was aided by conventional NMR experiments followed by chemical shift calculations using an X-ray crystal structure as reference that was in good agreement with H-H distances obtained from a new ROESY NMR method. The synthesis was compatible with silyl, trityl and dimethoxytrityl protecting groups. A new reagent mixture containing ZnCl2, Et3SiH and hexafluoroisopropanol was developed for detritylation of the acid-sensitive tricyclano nucleosides.
Synthesis and preliminary evaluation of pro-RNA 2′- O -masked with biolabile pivaloyloxymethyl groups in an RNA interference assay
Lavergne, Thomas,Baraguey, Carine,Dupouy, Christelle,Parey, Nora,Wuensche, Winfried,Sczakiel, Georg,Vasseur, Jean-Jacques,Debart, Francoise
scheme or table, p. 5719 - 5731 (2011/09/30)
The cellular delivery of bioactive nucleic acid-based drugs such as small interfering RNA (siRNA) represents a major technical hurdle for their pharmaceutical application. Prodrug-like approaches provide an attractive concept to address the delivery probl
General Method for the Synthesis of 2'-Azido-2',3'-dideoxynucleosides by the Use of -Hydride Shift and &β-Elimination Reactions
Kawana, Masajiro,Kuzuhara, Hiroyoshi
, p. 469 - 478 (2007/10/02)
The title nucleoside (16U, C, G and H) were synthesized from pyrimidine and purine ribonucleosides in about 30percent overall yield in 6 steps via key intermediates, protected 3'-deoxy-arabino-nucleosides, which were obtained by deoxygenative -hydrid