1345819-35-3Relevant academic research and scientific papers
Sequential directed epoxydation-acidolysis from glycals with MCPBA. A flexible approach to protected glycosyl donors
Marin, Irene,Castilla, Javier,Matheu, M. Isabel,Diaz, Yolanda,Castillon, Sergio
experimental part, p. 9622 - 9629 (2012/01/03)
4,6-Di-O-protected glucal and allal derivatives react with MCPBA to afford manno- and allo-1-O-m-chlorobenzoate derivatives, respectively, as a result of a syn epoxidation directed by the allylic hydroxyl group, and consecutive ring-opening by m-ClBzOH. When glucal and allal derivatives are fully protected, initial epoxidation proceeds mainly anti to the allylic group to give, after ring-opening, the corresponding pyranosyl chlorobenzoates. Stereoselectivity in the reaction of fully protected galactal derivatives was complete, although only a moderate increase in the syn epoxidation product was observed in 4,6- and 3,4-di-O-protected derivatives. 1-O-m-Chlorobenzoate 18 was selectively protected and activated as donor in the synthesis of disaccharide 21.
