Product Details of 676-96-0. The mechanism of aromatic electrophilic substitution of aromatic heterocycles is consistent with that of benzene. Compound: Trimethylphosphineoxide, is researched, Molecular C3H9OP, CAS is 676-96-0, about Hydrogen-Bonding-Assisted Exogenous Nucleophilic Reagent Effect for β-Selective Glycosylation of Rare 3-Amino Sugars. Author is Zeng, Jing; Wang, Ruobin; Zhang, Shuxin; Fang, Jing; Liu, Shanshan; Sun, Guangfei; Xu, Bingbing; Xiao, Ying; Fu, Dengxian; Zhang, Wenqi; Hu, Yixin; Wan, Qian.
Challenges for stereoselective glycosylation of deoxy sugars are notorious in carbohydrate chem. We herein report a novel strategy for the construction of the less investigated β-glycosidic bonds of 3,5-trans-3-amino-2,3,6-trideoxy sugars (3,5-trans-3-ADSs), which constitute the core structure of several biol. important antibiotics. Current protocol leverages a C-3 axial sulfonamide group in 3,5-trans-3-ADSs as a hydrogen-bond (H-bond) donor and substoichiometric phosphine oxide as an exogenous nucleophilic reagent (exNu) to establish an intramol. H-bond between the former and the derived α-oxyphosphonium ion. This pivotal interaction stabilizes the α-face-covered intermediate to inhibit the formation of the more reactive β-intermediate, thereby yielding reversed β-selectivity, which is unconventional for an ex-Nu-mediated glycosylation system. A wide range of substrates was accommodated, and good to excellent β-selectivities were ensured by this H-bonding-assisted exNu effect. The robustness of the current strategy was further attested by the architectural modification of natural products and drugs containing 3,5-trans-3-ADSs, as well as the synthesis of a trisaccharide unit in avidinorubicin.
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Reference:
Isoxazole – Wikipedia,
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