title: 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.
authors.affiliation: Department of Chemistry, Zhengzhou University, 100 Science Road, 450001 Zhengzhou, China. wshaomin@zzu.edu.cn
authors.forename: Shao-Min
authors.initials: SM
authors.lastname: Wang
authors.forename: Wei-Guo
authors.initials: WG
authors.lastname: Zhu
authors.forename: Jian-Xun
authors.initials: JX
authors.lastname: Kang
authors.forename: Hong-Min
authors.initials: HM
authors.lastname: Liu
authors.forename: Jun-Miao
authors.initials: JM
authors.lastname: Chen
authors.forename: Cui-Ping
authors.initials: CP
authors.lastname: Li
authors.forename: Kai
authors.initials: K
authors.lastname: Zhang
mesh_terms: D000107:Acetylation; D005960:Glucosides / Q000737:chemistry*; D009682:Magnetic Resonance Spectroscopy; D000432:Methanol / Q000737:chemistry; D009947:Organotin Compounds / Q000737:chemistry*
chemical_list: D005960:Glucosides; D009947:Organotin Compounds; C031078:dibutyltin oxide; D000432:Methanol