130405-48-0Relevant academic research and scientific papers
Reagent-Controlled Divergent Synthesis of C-Glycosides
Han, Pu-Ren,Liu, Jianchao,Liao, Jin-Xi,Tu, Yuan-Hong,Sun, Jian-Song
, p. 11449 - 11464 (2020/10/12)
By turning on or switching off the directing effect of the C3-OH-located o-diphenylphosphanylbenzoyl (o-DPPB) group in glycals, a reagent-controlled protocol for divergent and regio- and stereoselective syntheses of C-glycosides has been established. In particular, the silence of the directing effect of o-DPPB was achieved by the introduction of a ZnCl2 additive, which is operationally simple and efficient. The flexibility of the novel protocol was exhibited not only by the easy access of both α- and β-C-glycosides but also by the versatility of the obtained formal Ferrier rearrangement products, which can be easily derivatized to various C-glycoside analogues owing to the embedded multifunctionalities.
Skeletal diversity via cationic rearrangements of substituted dihydropyrans
Medeiros, Matthew R.,Narayan, Radha S.,McDougal, Nolan T.,Schaus, Scott E.,Porco Jr., John A.
supporting information; scheme or table, p. 3222 - 3225 (2010/10/05)
(Figure Presented) Substituted dihydropyrans, easily accessed from a commercially available glycal, undergo acid-catalyzed rearrangement to provide highly functionalized isochroman and dioxabicyclooctane scaffolds.
Exploring skeletal diversity via ring contraction of glycal-derived scaffolds
Yeager, Adam R.,Min, Geanna K.,Porco Jr., John A.,Schaus, Scott E.
, p. 5065 - 5068 (2007/10/03)
(Chemical Equation Presented) Aryl ether C-glycoside scaffolds have been prepared from tri-O-acetyl-D-glucal by C-glycosylation followed by allylic substitution with phenols mediated by Pd(0). The aryl ethers were subjected to either [3,3]-sigmatropic rea
Palladium-catalysed arylation of peracetylated glycals, III. Crystal structure of a by-product: mechanistic implications
Bellosta, Veronique,Czernecki, Stanislas,Avenel, Daniele,Bahij, Said El,Gillier-Pandraud, Helene
, p. 1364 - 1368 (2007/10/02)
Reinvestigation of the structure of (4,6-di-O-acetyl-2,3-dideoxy-α-D-erythro-hex-2-enopyranosyl)benzene, obtained by the title reaction, is described.The α anomeric configuration was clearly established by X-ray diffraction methods on the deacetylated com
