Hydrogenation of Sugar Enol-Ethers Using Pd/EtSiH Reagent System: A Route to Deoxy Sugars/Glycosides.

We have developed a hydrogenation method using Pd(OAc)/EtSiH as a reagent system for sugar enol ethers and their glycosides. This approach is highly effective and applicable to a wide range of glycals and glycosides, achieving yields up to 96% for the corresponding deoxy sugars. Applying standard conditions to various O/C-glycosides resulted in excellent transformation to 2,3-dideoxy glycosides.

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

The stereo- and regioselective formation of chiral molecules is an interesting and important topic in organic synthesis due to its wide applicability and intricacy during synthesis. Herein, we disclose a method for the selective functionalization of glycal dienes for synthesizing different glycosides and branched sugars stereo- and regioselectively. The methodology is broad regarding the substrate scope in which various nucleophiles and glycals were explored.

Pd-catalyzed stereoselective synthesis of chromone -glycosides.

Herein, we present an efficient Pd-catalysed method for stereoselective synthesis of chromone -glycosides from various glycals. We successfully applied this method to various glycals with different protecting groups, yielding the corresponding glycosides in 41-78% yields. Additionally, we investigated the potential of this approach for the late-stage modification of natural products and pharmaceutical compounds linked to glycals, leading to the synthesis of their respective glycosides.