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

Carbohydrate research (2010-12-28)
Shao-Min Wang, Wei-Guo Zhu, Jian-Xun Kang, Hong-Min Liu, Jun-Miao Chen, Cui-Ping Li, Kai Zhang
RESUMEN

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.

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Sigma-Aldrich
Dibutyltin(IV) oxide, 98%