106567-66-2Relevant academic research and scientific papers
Glycosyl Imidates, 25.- Muramic Acid as Glycosyl Donor and Glycosyl Acceptor
Kinzy, Willy,Schmidt, Richard R.
, p. 407 - 415 (2007/10/02)
From the 3-O-unprotected 2-azido-2-deoxy-D-glucose derivatives 3 and 4 and trifluoromethanesulfonates of (S)-lactate as alkylating agents the muramic acid derivatives 8a-10a were obtained diastereospecifically and in high yields. (S)-2-Chloropropionates afforded mixtures of diastereoisomers in this reaction.The muramic acid derivatives 8a-10a were readily transformed into glycosyl donors and glycosyl acceptors.Deacetalation of compounds 8a and 10a and subsequent selective 6-O-silylation afforded the glycosyl acceptor 11; reaction with α-trichloroacetimidate 14 as glycosyl donor provided the β-connected disaccharide 15-β.Deprotection yielded the disaccharide 19, the basic unit of the cell wall peptidoglycan of bacteria.Selective desilylation of the muramic acid derivative 8a and formation of the α-trichloroacetimidate 28-α provided a good muramic acid glycosyl donor.With various glycosyl acceptors depending on the catalyst and the reaction conditions either β- or α-glycosides and -disaccharides were obtained selectively and in high yields.
