1012045-70-3Relevant articles and documents
β-Selective Glycosylation by Using O-Aryl-Protected Glycosyl Donors
Otsuka, Yuji,Yamamoto, Toshihiro,Fukase, Koichi
, p. 2719 - 2723 (2019)
New glycosyl donors have been developed that contained several para-substituted O-aryl protecting groups and their stereoselectivity for the glycosylation reaction was evaluated. A highly β-selective glycosylation reaction was achieved by using thioglycosides that were protected by 4-nitrophenyl (NP) groups, which were introduced by using the corresponding diaryliodonium triflate. Analysis of the stereoselectivities of several glycosyl donors indicated that the β-glycosides were obtained through an SN2-type displacement from the corresponding α-glycosyl triflate. The NP group could be removed by reduction of the nitro group and acylation, followed by oxidation with ceric ammonium nitrate (CAN).
Application of glycosyl thioimidates in solid-phase oligosaccharide synthesis
Parlato, M. Cristina,Kamat, Medha N.,Wang, Haisheng,Stine, Keith J.,Demchenko, Alexei V.
, p. 1716 - 1725 (2008/09/18)
(Chemical Equation Presented) Two stable classes of thioimidoyl derivatives, S-benzoxazolyl (SBox) and S-thiazolinyl (STaz) glycosides, were investigated as glycosyl donors for solid-phase oligosaccharide synthesis. It was demonstrated that these derivatives are suitable for both glycosyl acceptor-bound and glycosyl donor-bound strategies, commonly employed in resin-supported oligosaccharide synthesis.