The reaction of an aromatic heterocycle with a proton is called a protonation. One of articles about this theory is 《Diarylborinic Acid-Catalyzed, Site-Selective Sulfation of Carbohydrate Derivatives》. Authors are Gorelik, Daniel; Lin, Yu Chen; Briceno-Strocchia, Alvaro I.; Taylor, Mark S..The article about the compound:(2R,3R,4S,5R,6R)-2-(Hydroxymethyl)-6-methoxytetrahydro-2H-pyran-3,4,5-triolcas:1824-94-8,SMILESS:O[C@H]([C@H]([C@H]([C@@H](CO)O1)O)O)[C@@H]1OC).Computed Properties of C7H14O6. Through the article, more information about this compound (cas:1824-94-8) is conveyed.
Sulfated carbohydrates have been implicated in diverse biol. processes, with the position and extent of sulfation of a glycoside often playing important roles in determining the affinity and specificity of its binding to a biomol. partner. Methods for the site-selective introduction of sulfate groups to carbohydrates are thus of interest. Here, we describe the development of a diarylborinic acid-catalyzed protocol for selective sulfation of pyranoside derivatives at the equatorial position of a cis-1,2-diol group. This method, which employs the sulfur trioxide-trimethylamine complex as the electrophile, has been employed for installation of a sulfate group at the 3-position of a range of galacto- and mannopyranosides, including substrates having a free primary OH group. By using a full equivalent of the diarylborinic acid, selective syntheses of more complex mono-sulfated glycosides, namely, a 3′-sulfolactose derivative and 3′-sulfo-β-galactosylceramide, have been accomplished. Preliminary kinetics experiments suggested that the catalyst resting state is a tetracoordinate diarylborinic ester that reacts with the SO3 complex in the turnover-limiting step. Catalyst inhibition by the pyranoside sulfate product and trialkylamine byproduct of the reaction was demonstrated.
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Reference:
Phosphine ligand,
Chiral phosphine ligands in asymmetric synthesis. Molecular structure and absolute configuration of (1,5-cyclooctadiene)-(2S,3S)-2,3-bis(diphenylphosphino)butanerhodium(I) perchlorate tetrahydrofuran solvate