Zinc(II) Iodide-Directed β-Mannosylation: Reaction Selectivity, Mode, and Application was written by Zhong, Xuemei;Zhou, Siai;Ao, Jiaming;Guo, Aoxin;Xiao, Qian;Huang, Yan;Zhu, Wanmeng;Cai, Hui;Ishiwata, Akihiro;Ito, Yukishige;Liu, Xue-Wei;Ding, Feiqing. And the article was included in Journal of Organic Chemistry in 2021.SDS of cas: 582-52-5 This article mentions the following:
A direct, efficient, and versatile glycosylation methodol. promises the systematic synthesis of oligosaccharides and glycoconjugates in a streamlined fashion like the synthesis of medium to long-chain nucleotides and peptides. The development of a generally applicable approach for the construction of 1,2-cis-glycosidic bond with controlled stereoselectivity remains a major challenge, especially for the synthesis of β-mannosides. Here, we report a direct mannosylation strategy mediated by ZnI2, a mild Lewis acid, for the highly stereoselective construction of 1,2-cis-β linkages employing easily accessible 4,6-O-tethered mannosyl trichloroacetimidate donors. The versatility and effectiveness of this strategy were demonstrated with successful β-mannosylation of a wide variety of alc. acceptors, including complex natural products, amino acids, and glycosides. Through iteratively performing ZnI2-mediated mannosylation with the chitobiosyl azide acceptor followed by site-selective deprotection of the mannosylation product, the novel methodol. enables the modular synthesis of the key intermediate trisaccharide with Man-β-(1→4)-GlcNAc-β-(1→4)-GlcNAc linkage for N-glycan synthesis. Theor. investigations with d. functional theory calculations delved into the mechanistic details of this β-selective mannosylation and elucidated two zinc cations’ essential roles as the activating agent of the donor and the principal mediator of the cis-directing intermol. interaction. In the experiment, the researchers used many compounds, for example, (3aR,5S,6S,6aR)-5-((R)-2,2-Dimethyl-1,3-dioxolan-4-yl)-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-6-ol (cas: 582-52-5SDS of cas: 582-52-5).
(3aR,5S,6S,6aR)-5-((R)-2,2-Dimethyl-1,3-dioxolan-4-yl)-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-6-ol (cas: 582-52-5) belongs to tetrahydrofuran derivatives. THF (Tetrahydrofuran) is a stable compound with relatively low boiling point and excellent solvency. Oxidations have also proved to be valuable and efficient approaches to chiral tetrahydrofuran derivatives.SDS of cas: 582-52-5
Referemce:
Tetrahydrofuran – Wikipedia,
Tetrahydrofuran | (CH2)3CH2O – PubChem