ESIMS and NMR studies on the selective deprotection of acetylated glucosides by dibutyltin oxide.

ABSTRACT

The reaction process for the selective deprotection of acetylated glucosides by dibutyltin oxide in methanol is investigated by using methyl 2,3,4,6-tetra-O-acetyl-α-d-glucopyranoside as a model substrate with ESIMS and NMR techniques. According to the results, it is inferred that at first, dimeric 1,3-dimethoxytetrabutyldistannoxane is formed by the reaction of dibutyltin oxide with methanol, and then the tetraorganodistannoxane reacts with the acetylated glucoside to produce glucoside-organotin complex intermediates. Finally, the complex intermediates are hydrolyzed leading to the free-OH glucoside and organotin acetate derivatives. The reaction is affected by neighboring group participation and steric hindrance, which allow for high selectivities among different acetyl groups in acetylated glucosides.