title: A general method for N-glycosylation of nucleobases promoted by (p-Tol)2SO/Tf2O with thioglycoside as donor.
abstract: 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.
authors.affiliation: Department of Chemistry, Beijing Normal University, Beijing 100875, China. gwxing@bnu.edu.cn.
authors.forename: Guang-jian
authors.initials: GJ
authors.lastname: Liu
authors.forename: Xiao-tai
authors.initials: XT
authors.lastname: Zhang
authors.forename: Guo-wen
authors.initials: GW
authors.lastname: Xing
mesh_terms: D002384:Catalysis; D006001:Glycoconjugates / Q000737:chemistry; D006031:Glycosylation; D008698:Mesylates / Q000737:chemistry*; D013237:Stereoisomerism; D013454:Sulfoxides / Q000737:chemistry*; D013865:Thioglycosides / Q000737:chemistry*
chemical_list: D006001:Glycoconjugates; D008698:Mesylates; D013454:Sulfoxides; D013865:Thioglycosides; C012077:trifluoromethanesulfonic acid