ESIMS and NMR studies on the selective deprotection of acetylated glucosides by dibutyltin oxide.
Carbohydr Res
; 346(2): 203-9, 2011 Feb 01.
Article
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| MEDLINE
| ID: mdl-21185014
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.
Texto completo:
1
Bases de datos:
MEDLINE
Asunto principal:
Compuestos Orgánicos de Estaño
/
Glucósidos
Idioma:
En
Revista:
Carbohydr Res
Año:
2011
Tipo del documento:
Article
País de afiliación:
China