63087-91-2Relevant academic research and scientific papers
Combined Lewis acid and Br?nsted acid-mediated reactivity of glycosyl trichloroacetimidate donors
Gould, Nathan D.,Liana Allen,Nam, Brandon C.,Schepartz, Alanna,Miller, Scott J.
, p. 36 - 42 (2013)
Biomimetic conditions for a synthetic glycosylation reaction, inspired by the highly conserved functionality of carbohydrate active enzymes, were explored. At the outset, we sought to generate proof of principle for this approach to developing catalytic systems for glycosylation. However, control reactions and subsequent kinetic studies showed that a stoichiometric, irreversible reaction of the catalyst and glycosyl donor was occurring, with a remarkable rate variance depending upon the structure of the carboxylic acid. It was subsequently found that a combination of Br?nsted acid (carboxylic acid) and Lewis acid (MgBr2) was unique in catalyzing the desired glycosylation reaction. Thus, it was concluded that the two acids act synergistically to catalyze the desired transformation. The role of the catalytic components was tested with a number of control reactions and based on these studies a mechanism is proposed herein.
SYNTHESES OF 1-O-ACYLALDOSE DERIVATIVES via THE CORRESPONDING O-GLYCOSYLPSEUDOUREAS
Tsutsumi, Hideo,Ishido, Yoshiharu
, p. 75 - 84 (2007/10/02)
A series of 1-O-acylaldose derivatives was prepared in good yield throught the reaction of 1,3-dialkyl-O-glycosylpseudoureas with carboxylic acids.
