1447935-18-3Relevant academic research and scientific papers
Application of 2-substituted benzyl groups in stereoselective glycosylation
Buda, Szymon,Nawj, Miroslaw,Golbiowska, Patrycja,Dyduch, Karol,Michalak, Artur,Mlynarski, Jacek
, p. 770 - 780 (2015/03/03)
The use of 2-O-(2-nitrobenzyl) and 2-O-(2-cyanobenzyl) groups controls stereoselective formation of 1,2-trans-glycosidic linkages via the arming participation effect. The observed stereoselectivity likely arises from the intramolecular formation of cyclic intermediate between the electron-rich substituent and the donor oxacarbenium ion providing the expected facial selectivity for attack of the glycoside acceptor. The stereodirecting effect of the 2-nitro- and 2-cyanobenzyl groups attached at the remote position (C-3, C-4, and C-6) of the donor molecule have also been investigated. To prove the postulated mechanism based on the participation effect of 2-substituted benzyl groups in the glycosylation stereoselectivity we used DFT theoretical calculation methodology.
Application of the 2-nitrobenzyl group in glycosylation reactions: A valuable example of an arming participating group
Buda, Szymon,Golebiowska, Patrycja,Mlynarski, Jacek
, p. 3988 - 3991 (2013/07/19)
The application of the o-nitrobenzyl (oNBn) group is demonstrated. This practical methodology allows the stereocontrolled synthesis of glucosides with a 1,2-trans linkage. This new ether-type arming group can broadly extend the concept of the use of participating groups in glycosylation reactions. Easy protection and deprotection of the oNBn group further confirms its usefulness in synthesis. The application of o-nitrobenzyl (oNBn) ether as an arming participating group is demonstrated. This practical methodology allows the stereocontrolled synthesis of glucosides with a 1,2-trans linkage. Copyright
