Anodic Reactivity of Alkyl S-Glucosides was written by Deore, Bhavesh;Ocando, Joseph E.;Pham, Lan D.;Sanhueza, Carlos A.. And the article was included in Journal of Organic Chemistry in 2022.Electric Literature of C16H22O11 The following contents are mentioned in the article:
A voltammetric study of a series of alkyl and aryl S-glucosides unveiled the reactivity patterns of alkyl S-glucosides toward anodic oxidation and found noteworthy differences with the trends followed by aryl derivatives The oxidation potential of alkyl S-glucosides, estimated herein from square-wave voltammetry peak potentials (Ep), depends on the steric properties of the aglycon. Glucosides substituted with bulky groups exhibit Ep values at voltages more pos. than the values of those carrying small aglycons. This relationship, observed in all analyzed alkyl series, is evidenced by good linear correlations between Ep and Taft’s steric parameters (ES) of the resp. alkyl substituents. Moreover, the role of the aglycon’s steric properties as a primary reactivity modulator is backed by poor correlations between Ep and the radical stabilization energies (RSEs) of the aglycon-derived thiyl radicals (RS•). In contrast, aryl glucosides’ Ep values exhibit excellent correlations with the aryl substituents’ Hammett parameters (σ+) and the ArS• RSEs, evidencing the inherent stability of the reactive radical intermediate as the primary factor controlling aryl glucoside’s electrochem. reactivity. The reactivity differences between alkyl and aryl S-glucosides also extend to the protective group’s effect on Ep. Alkyl S-glucosides’ reactivity proved to be more sensitive to protective group exchange. This study involved multiple reactions and reactants, such as (2S,3R,4S,5R,6R)-6-(Acetoxymethyl)tetrahydro-2H-pyran-2,3,4,5-tetrayl tetraacetate (cas: 604-69-3Electric Literature of C16H22O11).
(2S,3R,4S,5R,6R)-6-(Acetoxymethyl)tetrahydro-2H-pyran-2,3,4,5-tetrayl tetraacetate (cas: 604-69-3) belongs to esters. Esters perform as high-grade solvents for a broad array of plastics, plasticizers, resins, and lacquers, and are one of the largest classes of synthetic lubricants on the commercial market. Esters are more polar than ethers but less polar than alcohols. They participate in hydrogen bonds as hydrogen-bond acceptors, but cannot act as hydrogen-bond donors, unlike their parent alcohols. This ability to participate in hydrogen bonding confers some water-solubility.Electric Literature of C16H22O11
Referemce:
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics