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

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
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.

MATERIALS
Product Number
Brand
Product Description

Sigma-Aldrich
Dibutyltin(IV) oxide, purum
Sigma-Aldrich
Dibutyltin(IV) oxide, 98%