Straightforward S-S Bond Formation via the Oxidation of S-Acetyl by Iodine in the Presence of N-Iodosuccinimide.

Straightforward S-S bond formation via the oxidation of S-acetyl group by iodine was reported here. The reaction was further applied in the synthesis of per-O-acetylated glycosyl disulfides. These studies demonstrated great improvement in reaction rate, yield, and general convenience in the presence of N-iodosuccinimide. Furthermore, selectively deacetylated glycosyl thiols were obtained in high yields when these per-O-acetylated glycosyl disulfides were reduced with tris(2-carboxyethyl)-phosphine (TCEP). Our method supplied an efficient way to obtain both per-O-acetylated glycosyl disulfides and per-O-acetylated glycosyl thiols in which the sulfur group was located at any position.