97626-95-4Relevant academic research and scientific papers
A general method for N-glycosylation of nucleobases promoted by (p-Tol)2SO/Tf2O with thioglycoside as donor
Liu, Guang-Jian,Zhang, Xiao-Tai,Xing, Guo-Wen
, p. 12803 - 12806 (2015/08/06)
Based on a preactivation strategy using the (p-Tol)2SO/Tf2O system, a series of nucleosides were synthesized by coupling various thioglycosides with pyrimidines and purines under mild conditions. High yields and excellent β-stereoselectivities were obtained with either armed or disarmed N-glycosylation donors by tuning the amount of (p-Tol)2SO additive.
An efficient approach to the synthesis of nucleosides: Gold(I)-catalyzed N-glycosylation of pyrimidines and purines with glycosyl ortho-alkynyl benzoates
Zhang, Qingju,Sun, Jiansong,Zhu, Yugen,Zhang, Fuyi,Yu, Biao
supporting information; experimental part, p. 4933 - 4936 (2011/06/24)
Persuaded with gold: The title reaction in the presence of [Ph 3PAuNTf2] (Tf=trifluoromethanesulfonyl) led conveniently to the corresponding nucleosides with excellent regioselectivity (see scheme). Even purine derivatives underwent this transformation owing to the mild conditions, which enabled the use of protecting groups that would not usually be compatible with N-glycosylation conditions. Copyright
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.
