1269490-06-3Relevant academic research and scientific papers
A new method for selective deprotection of anomeric N,O -dimethylhydroxylamine promoted by TMSCl
Huang, Shengjun,Liao, Jun,Zhao, Qingjie,Chai, Xiaoyun,Wang, Baogang,Yu, Shichong,Wu, Qiuye
, p. 158 - 168 (2013/03/29)
TMSCl was shown to be an efficient reagent for selective deprotection of the anomeric position protected as N,O-dimethylhydroxylamine glycoside. This deprotection condition was proved to be compatible with a number of protecting groups, such as the TBDPS, acetyl, benzyl, benzylidene, and benzoyl groups.Copyright Taylor and Francis Group, LLC.
Use of N,O-dimethylhydroxylamine as an anomeric protecting group in carbohydrate synthesis
Dasgupta, Somnath,Nitz, Mark
supporting information; experimental part, p. 1918 - 1921 (2011/06/24)
The N,O-dimethyloxyamine-N-glycosides are introducedas anomerically protected building blocks for carbohydrate synthesis. These N-glycosides are stable to a variety of protecting group manipulations including acylation, alkylation, silylation, and acetal formation. The alkoxyamine-N-glycosides can be cleaved selectively with N-chlorosuccinimide to give the desired hemiacetals in excellent yield. Furthermore, these Nglycosides are stable to the activation conditions required for glycosylation using thioglycoside and trichloroacetimidate glycosyl donors suggesting N,O-dialkoxyamine-N-glycosides will be useful for complex oligosaccharide synthesis.
