Regioselective direct sulfenylation of glycals using arylsulfonyl chlorides in the presence of triphenylphosphine: access to C2-thioaryl glycosides

Abstract

Direct triphenylphosphine mediated regioselective sulfenylation of glycals by using cheap and easily available various aryl sulfonyl chlorides as a sulfur source to generate different C2-S-aryl-glycosides was developed. Notably, features of...

Site-Selective Lewis Acid Mediated Transformation of Pseudo Glycals to 1-Deoxy-2-thioaryl/alkyl Glycosides

“…13 More recently, the Mandal group developed PPh 3 -mediated direct thioarylation by utilizing the C2-position of glycals and arylsulfonyl chlorides. 14 Despite the development towards the synthesis of C2 thioaryl glycals, there is space to improve the current methodologies by avoiding the use of metals, stoichiometric phosphines, and elevated temperature. In continuation of our research on the functionalization of glycals using C2-position, 15 16 17 we were curious to utilize the pseudoglycals having a double bond at the C2/3 position of glycals towards the synthesis of C2-functionalized thioglycosides (Scheme 1 ).…”

Directed Dehydrogenative Copper‐Catalyzed C−H Thiolation in Pseudo‐Anomeric Position of Glycals using Thiol and Thiosugar Partners

“…The crude was finally purified on silica gel using the indicated solvent. [24] To a solution of KF (6.1 mg, 0.1054 mmol) in CH 3 CN/H 2 O (0.6 mL; v/v 5:1), 70% m-CPBA (18.2 mg, 0.1054 mmol) was added and the reaction mixture was stirred at 0 °C for 30 min. To the ice-cooled reaction mixture was added (3 a, 50 mg, 0.0527 mmol) and the mixture was stirred at 0 °C for 30 min.…”

Reactivity Switch in Glycal Dienes toward Different Nucleophiles: Mechanistic Insight and Applications toward the Synthesis of Naphthalene-Fused Pyran Derivatives

“…Glycal-derived dienes can be readily synthesized through C− H activation or cross-coupling reactions, 12,16,17 serving as versatile synthons for assembling diverse annulated sugars and chiral aromatic building blocks. In our ongoing investigation into the reactivity of glycals and their derivatives, we hypothesized that glycal dienes exhibit a conjugated system and could be effective substrates for the regio-and stereoselective incorporation of external nucleophiles.…”