Regioselective Protection at the Secondary Positions of Carbohydrates with Acyclic Protecting Groups

Advances in glycoside and oligosaccharide synthesis

“…Particularly valuable are protecting groups and methods that permit the selective modification of carbohydrate polyols such as benzylidene acetals that can be regioselectively opened under reductive conditions. [98][99][100][101][102] Some one-pot protocols allow for the preparation of advanced synthetic intermediates. [103][104][105] Dibutyltin oxide and diarylborinic acid catalysts enable regioselective acylation or alkylation in the presence of multiple hydroxyl groups.…”

Trivalent dialkylaminopyridine-catalyzed site-selective mono-O-acylation of partially-protected pyranosides

“…Protecting group methods enable the chemical synthesis of oligosaccharides and polysaccharides in the most achievable homogeneous manner. 6,7 The p K a of primary and secondary hydroxy functionalities are within 16–18, implying that reactivity differences are minimal among these functionalities. As a result, development of methods for the site-selective modification of carbohydrates, 8 including one-pot synthetic methods, 9 is important.…”

Synthesis of carbohydrate building blocksviaregioselective uniform protection/deprotection strategies

“…Steric hindrance, as well as the electronic effects, can also be utilized to some extent to discriminate between certain secondary hydroxyl groups. 18 In addition, hydrogen bond networks were also proposed as a possible driving force for the regioselective protection.…”