1311109-55-3Relevant articles and documents
NIS/TMSOTf-Promoted Glycosidation of Glycosyl ortho-Hexynylbenzoates for Versatile Synthesis of O-Glycosides and Nucleosides
Liu, Rongkun,Hua, Qingting,Lou, Qixin,Wang, Jiazhe,Li, Xiaona,Ma, Zhi,Yang, You
, p. 4763 - 4778 (2021/04/06)
Glycosidation plays a pivotal role in the synthesis of O-glycosides and nucleosides that mediate a diverse range of biological processes. However, efficient glycosidation approach for the synthesis of both O-glycosides and nucleosides remains challenging in terms of glycosidation yields, mild reaction conditions, readily available glycosyl donors, and cheap promoters. Here, we report a versatile N-iodosuccinimide/trimethylsilyl triflate (NIS/TMSOTf)-promoted glycosidation approach with glycosyl ortho-hexynylbenzoates as donors for the highly efficient synthesis of O-glycosides and nucleosides. The glycosidation approach highlights the merits of mild reaction conditions, cheap promoters, extremely wide substrate scope, and good to excellent yields. Notably, the glycosidation approach performs very well in the construction of a series of challenging O- and N-glycosidic linkages. The glycosidation approach is then applied to the efficient synthesis of oligosaccharides via the one-pot strategy and the stepwise strategy. On the basis of the isolation and characterization of the departure species derived from the leaving group, a plausible mechanism of NIS/TMSOTf-promoted glycosidation of glycosyl ortho-hexynylbenzoates is proposed.
Ortho-(1-phenylvinyl)benzoate glycosylation donor, and preparation method and application thereof
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Paragraph 0103; 0107; 0169-0170, (2020/05/01)
The invention discloses an ortho-(1-phenylvinyl)benzoate glycosylation donor, and a preparation method and an application thereof in a glycosylation reaction. The ortho-(1-phenylvinyl)benzoate glycosylation donor is stable, is easy to prepare and store, and is widely applied to the construction of various oxygen glucosides and nucleoside (nitrogen glucoside) glycosidic bonds. The leaving group ofthe donor is an alkenyl ester, has a high activity, and can be combined with thioglycoside or n-pentenyl ether glucoside through a one-pot glycosylation reaction to synthesize oligosaccharide. The glycosylation reaction conditions are mild, and receptors sensitive to acid and electrophilic reagents can tolerate the glycosylation reaction conditions.
Base glycosylation method taking o-alkylenyl phenol ether as leaving group
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Paragraph 0116-0118; 0119-0121; 0160-0161, (2019/07/04)
The invention discloses a method for building C-N glycosidic bond of nucleoside. The method is simple in operation, mild in condition and high in stereoselectivity and regioselectivityof reaction. Themethod includes: taking o-alkylenyl phenol ether as the
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
supporting information, 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
