Protecting group principles suited to late stage functionalization and global deprotection in oligosaccharide synthesis

Catalytic Orthogonal Glycosylation Enabled by Enynal‐Derived Copper Carbenes

“…[29] The methyl-tri-O-benzyl-α-D-glucopyranoside 4 a was selected as the acceptor to optimize the reaction conditions so that the resulting product can undergo global deprotection (Pd/C + H 2 ) to provide the unprotected disaccharide. [30] We focused on identifying the optimal components among earth-abundant metal catalysts, acid scavengers, and solvents (Table 1). Through our studies, we determined that the highest yield (90%) and desired 1,2-cis-diastereoselectivity (α:β = 1:8) could be achieved using 30 mol% Cu-(I)OTf as the catalyst, lithium carbonate (1.5 equiv.)…”

Advances in glycoside and oligosaccharide synthesis

“…This ''global deprotection'' at the final stage is often the least optimised part of the synthesis. [458][459][460][461][462] High-quality reagents are essential to maximise the yields of target glycans, especially in the case of hydrogenolysis reactions, where the quality of palladium on carbon catalysts varies widely among commercial suppliers. 463 Additional consideration should be given to the glycan structure, the role of solvent(s) (and solvent combinations), 464,465 temperature(s) and pressure(s), that can play a decisive role in determining the success of the hydrogenolysis reaction.…”

Lignocellulosic–biomolecules conjugated systems: green-engineered complexes modified by covalent linkers

“…[6][7][8][9][10][11][12][13][14][15][16][17][18] The primary biomolecules in bioconjugate systems include lipids, proteins, nucleic acids, and carbohydrates. [19][20][21][22][23][24] Lignocellulosic structures are notable in the carbohydrate-bioconjugate domain (Fig. 1) and have garnered increased research interest in the last decade.…”