A varied set of solvent-free, one-pot synthetic sequences were developed to carry out the orthogonal protection of saccharide polyols. These sequences are composed of an initial regioselective benzylation, silylation or iodination (under mildly basic conditions), followed by an acid catalyzed protection of two further hydroxyl sites via the generation of a cyclic acetal. These processes allow recycling of the ammonium or pyridinium side products generated in the former step as effective catalytic species for the latter step.
One-pot synthesis of orthogonally protected sugars through sequential base-promoted/acid-catalyzed steps: A solvent-free approach with self-generation of a catalytic species / Traboni, Serena; Bedini, Emiliano; Giordano, Maddalena; Iadonisi, Alfonso. - In: TETRAHEDRON LETTERS. - ISSN 0040-4039. - 60:(2019), pp. 1777-1780. [10.1016/j.tetlet.2019.05.066]
One-pot synthesis of orthogonally protected sugars through sequential base-promoted/acid-catalyzed steps: A solvent-free approach with self-generation of a catalytic species
Serena Traboni;Emiliano Bedini;GIORDANO, MADDALENA;Alfonso Iadonisi
2019
Abstract
A varied set of solvent-free, one-pot synthetic sequences were developed to carry out the orthogonal protection of saccharide polyols. These sequences are composed of an initial regioselective benzylation, silylation or iodination (under mildly basic conditions), followed by an acid catalyzed protection of two further hydroxyl sites via the generation of a cyclic acetal. These processes allow recycling of the ammonium or pyridinium side products generated in the former step as effective catalytic species for the latter step.I documenti in IRIS sono protetti da copyright e tutti i diritti sono riservati, salvo diversa indicazione.
