474426-99-8Relevant academic research and scientific papers
The synthesis of cyclic imidates from amides of glucuronic acid and investigation of glycosidation reactions
Cronin, Linda,Tosin, Manuela,Mueller-Bunz, Helge,Murphy, Paul V.
, p. 111 - 118 (2007/10/03)
The synthesis of novel cyclic glycosyl imidates and an investigation of their potential as donors in glycosidation reactions is described. The results show that 1,2-cis glycosides obtained from the reactions of glycosyl acetates or cyclic imidates, each d
Synthesis of α-glucuronic acid and amide derivatives in the presence of a participating 2-acyl protecting group
Tosin, Manuela,Murphy, Paul V.
, p. 3675 - 3678 (2007/10/03)
(graph presented) Participating acyl groups located at C-2 in glucosyl and related donors generally promote formation of 1,2-trans-glycosides. Reactions of some glucuronic acid donors with TMSN3/SnCl4 or ROH/SnCl4 gave only the 1,2-cis-glycoside. The stereoselectivity is consistent with participation of the C-6 group. The methodology was used for the synthesis of a Kdn2en mimetic with the α-configuration.
