30747-21-8Relevant academic research and scientific papers
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 reinvestigated mechanism of ribosylation of adenine under silylating conditions
Framski, Grzegorz,Gdaniec, Zofia,Gdaniec, Maria,Boryski, Jerzy
, p. 10123 - 10129 (2007/10/03)
The mechanism of chemical synthesis of adenosine has been reinvestigated. Depending on the reaction conditions and the presence of N6-protecting groups, ribosylation of adenine proceeds via different kinetic products: 3-riboadenine in strongly acidic media, 7-ribosylated derivative in the silyl method, and 1-(β-d-ribofuranosyl)adenine when applying N6-acyladenine and silylating conditions.
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.
Solution and solid phase chemical synthesis of arabinonucleotides
Damha, Masad Jose,Usman, Nassim,Ogilvie, Kelvin Kenneth
, p. 831 - 839 (2007/10/02)
A fast and convenient procedure for the chemical synthesis of arabinonucleotides, which eliminates the multistep protection of the arabinonucleoside building blocks, is described.The results of these studies were successfully applied to the automated chem
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
