title: ortho-Methylphenylthioglycosides as glycosyl building blocks for preactivation-based oligosaccharide synthesis.
abstract: Thioglycosides are widely used in orthogonal glycosylation, armed-disarmed chemoselective glycosylation, and preactivation-based glycosylation. Nevertheless, aglycon transfer occasionally occurred in the glycosylation process of thioglycosides. This problem was also encountered in preactivation-based reactions, which limited the applications of preactivation-based glycosylation to some extent. To tackle this problem, sterically hindered aglycon ortho-methylphenylthioglycosides were introduced as glycosyl building blocks. These thioglycosides prevented the aglycon transfer and enhanced the efficiency of glycosyl coupling reactions, especially in the reactions of disarmed donors with armed acceptors. Moreover, these thioglycosides were employed in preactivation-based one-pot oligosaccharide assembly.
authors: State Key Laboratory of Natural and Biomimetic Drugs, School of Pharmaceutical Sciences, Peking University, Xue Yuan Rd No. 38, Beijing 100191, China.
authors: Peng
authors: P
authors: Peng
authors: State Key Laboratory of Natural and Biomimetic Drugs, School of Pharmaceutical Sciences, Peking University, Xue Yuan Rd No. 38, Beijing 100191, China.
authors: De-Cai
authors: DC
authors: Xiong
authors: State Key Laboratory of Natural and Biomimetic Drugs, School of Pharmaceutical Sciences, Peking University, Xue Yuan Rd No. 38, Beijing 100191, China. Electronic address: xinshan@bjmu.edu.cn.
authors: Xin-Shan
authors: XS
authors: Ye
mesh_terms: D015394:Molecular Structure; D009844:Oligosaccharides / Q000138:chemical synthesis* / Q000737:chemistry*; D013865:Thioglycosides / Q000737:chemistry*; D014050:Toluene / Q000031:analogs & derivatives* / Q000737:chemistry
chemical_list: D009844:Oligosaccharides; D013865:Thioglycosides; D014050:Toluene
keywords: Aglycon transfer; Glycosylation; Oligosaccharide; Preactivation; o-Methylphenylthioglycoside