30747-21-8Relevant articles and documents
Selective deacylation of peracylated ribonucleosides
Rigoli, Jared W.,?stergaard, Michael E.,Canady, Kirsten M.,Guenther, Dale C.,Hrdlicka, Patrick J.
supporting information; experimental part, p. 1751 - 1753 (2009/07/05)
A protocol for chemoselective deprotection of N,O-acylated ribonucleosides has been developed. Peracylated pyrimidine ribonucleosides subjected to guanidinium nitrate and NaOMe in MeOH/CH2Cl2 at 0 °C undergo high yielding O-deacylation, while even more pronounced chemoselectivity is observed with peracylated purine ribonucleosides as O5′-acyl groups are preserved. Nucleobase-protecting groups (ABz, CBz, GiBu, and UBz) are stable to these conditions, rendering this reagent mixture as a valuable addition to the collection of protecting group protocols in nucleoside chemistry.
A direct, efficient method for the preparation of N6-protected 15N-labeled adenosines
Terrazas, Montserrat,Ariza, Xavier,Farras, Jaume,Guisado-Yang, Jose M.,Vilarrasa, Jaume
, p. 5473 - 5475 (2007/10/03)
N6-Protected adenosines have been prepared from inosines by activation of the C6 position and Pd-catalyzed coupling with amides. An efficient route to [6-15-NH2]-N6- benzoyladenosine and [1-15N,6-15NH2]-N 6-benzoyladenosine has been achieved.
The Prominent Effect of N6-Acyl Groups on the Reactivity of 9-Substituted Adenines: A New Method for the Chemical Modification of Adenines
Maki, Yoshifumi,Kameyama, Keiji,Suzuki, Mikio,Sako, Magoichi,Hirota, Kosaku
, p. 3601 - 3654 (2007/10/02)
The effect of various N6-substituents on the C(8)-hydrogen exchange of 9-substituted adenines has been estimated.The kinetic data clearly demonstrate that the N6-acyl groups significantly accelerate the C(8)-hydrogen exchange.This fa