71528-64-8Relevant articles and documents
Tris(pentafluorophenyl)borane-promoted stereoselective glycosylation with glycosyl trichloroacetimidates under mild conditions
Mishra, Kunj Bihari,Singh, Adesh Kumar,Kandasamy, Jeyakumar
, p. 4204 - 4212 (2018)
Tris(pentafluorophenyl)borane-promoted stereoselective glycosylation with trichloroacetimidate glycosyl donors is described. The reactions proceed efficiently with a wide range of acceptors, from sugar to nonsugar, under mild conditions in the presence of
A "traceless" Directing Group Enables Catalytic SN2 Glycosylation toward 1,2- cis-Glycopyranosides
Fu, Yue,Liu, Peng,Ma, Xu,Zhang, Liming,Zheng, Zhitong,Zhu, Xijun
supporting information, p. 11908 - 11913 (2021/08/20)
Generally applicable and stereoselective formation of 1,2-cis-glycopyranosidic linkage remains a long sought after yet unmet goal in carbohydrate chemistry. This work advances a strategy to this challenge via stereoinversion at the anomeric position of 1,2-trans glycosyl ester donors. This SN2 glycosylation is enabled under gold catalysis by an oxazole-based directing group optimally tethered to a leaving group and achieved under mild catalytic conditions, in mostly excellent yields, and with good to outstanding selectivities. The strategy is also applied to the synthesis of oligosaccharides.
Ferrocenium complex aided: O-glycosylation of glycosyl halides
Bauer, Eike B.,Talasila, Deva Saroja
, p. 36814 - 36820 (2021/12/02)
A new strategy for the activation of glycosyl halide donors to be utilized in glycosylation reactions is presented, utilizing the ferrocenium (Fc) complexes [FcB(OH)2]SbF6 and FcBF4 as promoters. The scope of the new system has been investigated using glycosyl chloride and glycosyl fluoride donors in combination with common glycosyl acceptors, such as protected glucose. The corresponding glycosylation products were formed in 95 to 10% isolated yields with α/β ratios ranging from 1/1 to β only (2 to 14 h reaction time at room temperature, 40 to 100% ferrocenium promoter load). This journal is
A visible light promoted O-glycosylation with glycosyl trichloroacetimidates using eosin Y as an organo photoacid
Li, Hongfang,Liu, Jiao,Ni, Guanghui,Wang, Haimei,Yin, Shan
, (2020/03/06)
A photoacid catalyzed O-glycosylation of alcohols with glycosyl trichloroacetimidates in the presence of commercially available phenolic photoacids, fluorescein, 4′,5′-dibromo-fluorescein, and eosin Y under visible light irradiation by blue LEDs was devel
Visible light promoted method for constructing O-glycoside bonds
-
Paragraph 0028-0029, (2020/07/13)
The invention discloses a visible light promoted method for constructing O-glycoside bonds. Glycosyl trichloroacetimidate is taken as a donor, and phenolic compounds are taken as a photocatalyst; a molecular sieve is added; and the O-glycoside bonds are g
Cholesteryl 6-: O-acyl-α-glucosides from diverse Helicobacter spp. signal through the C-type lectin receptor Mincle
Ito, Emi,Smith, Dylan G. M.,Williams, Spencer J.,Yamasaki, Sho
, p. 7907 - 7915 (2020/11/02)
Helicobacter spp. are Gram-negative bacteria that cause a spectrum of disease in the gut, biliary tree and liver. Many Helicobacter spp. produce a range of cholesteryl α-glucosides that have the potential to act as pathogen associated molecular patterns. We report a highly stereoselective α-glucosylation of cholesterol using 3,4,6-tri-O-acetyl-2-O-benzyl-d-glucopyranosyl N-phenyl-2,2,2-trifluoroacetimidate, which allowed the synthesis of cholesteryl α-glucoside (αCG) and representative Helicobacter spp. cholesteryl 6-O-acyl-α-glucosides (αCAGs; acyl = C12:0, 14:0, C16:0, C18:0, C18:1). All αCAGs, irrespective of the nature of their acyl chain composition, strongly agonised signalling through the C-type lectin receptor Mincle from human and mouse to similar degrees. By contrast, αCG only weakly signalled through human Mincle, and did not signal through mouse Mincle. These results provide a molecular basis for understanding of the immunobiology of non-pylori Helicobacter infections in humans and other animals. This journal is
Efficient glycosylation with glycosyl ortho-allylbenzoates as donors
Liang, Haijing,Ma, Lixia,Li, Changwei,Peng, Qiang,Wang, Zhaoyan,Zhang, Zhan-xin,Yu, Lan,Liu, Huanxiang,An, Fengli,Xue, Weihua
supporting information, p. 84 - 87 (2018/11/30)
Glycosylation reactions are significant as they provide access to model compounds that are useful for elucidating biochemical pathways. Herein, we describe the development of glycosyl ortho-alkynylbenzoates as novel, bench-top stable, and readily availabl
Silver-catalyzed stereoselective formation of glycosides using glycosyl ynenoates as donors
Dong, Xu,Chen, Li,Zheng, Zhitong,Ma, Xu,Luo, Zaigang,Zhang, Liming
supporting information, p. 8626 - 8629 (2018/08/06)
A silver-catalyzed glycosylation reaction employing readily accessible and stable glycosyl ynenoates is developed. This reaction is mostly high yielding and exhibits varying levels of stereoinversion at the anomeric position. Compared to established and versatile Yu's gold catalysis, this chemistry features the use of substantially cheaper AgNTf2.
O-(p-Methoxyphenylethynyl)phenyl Glycosides: Versatile New Glycosylation Donors for the Highly Efficient Construction of Glycosidic Linkages
Hu, Yang,Yu, Ke,Shi, Li-Li,Liu, Lei,Sui, Jing-Jing,Liu, De-Yong,Xiong, Bin,Sun, Jian-Song
, p. 12736 - 12744 (2017/09/25)
A novel alkyne-activation-based glycosylation protocol using o-(p-methoxyphenylethynyl)phenyl (MPEP) glycoside was established. The glycosyl MPEP donors were shelf-stable and could be prepared efficiently via Sonogashira reaction from the corresponding o-
