- A new method for selective deprotection of anomeric N,O -dimethylhydroxylamine promoted by TMSCl
-
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.
- Huang, Shengjun,Liao, Jun,Zhao, Qingjie,Chai, Xiaoyun,Wang, Baogang,Yu, Shichong,Wu, Qiuye
-
p. 158 - 168
(2013/03/29)
-
- Use of N,O-dimethylhydroxylamine as an anomeric protecting group in carbohydrate synthesis
-
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.
- Dasgupta, Somnath,Nitz, Mark
-
supporting information; experimental part
p. 1918 - 1921
(2011/06/24)
-