Protecting-Group-Free Synthesis of Chondroitin 6-Sulfate Disaccharide and Tetrasaccharide.

Chondroitin 6-sulfate (CS-C) is an important glycosaminoglycan that regulates many physiological functions including the development, progression, and metastasis of cancer. To understand its mechanism of action at the molecular level, CS-C molecules of defined length are required. A protecting group-free synthesis of CS-C disaccharide and tetrasaccharide from the CS-A polymer that involves only three steps and furnishes CS-O disaccharide and tetrasaccharide as intermediates is reported.