Journal
JOURNAL OF ORGANIC CHEMISTRY
Volume 73, Issue 22, Pages 8838-8850Publisher
AMER CHEMICAL SOC
DOI: 10.1021/jo801551r
Keywords
-
Categories
Funding
- National Institutes of General Medical Sciences [GM077170]
- ACS PRF [42397-G1]
- NSF [CHE-9974801, CHE-9708640]
Ask authors/readers for more resources
A new method for stereocontrolled glycosylation and chemoselective oligosaccharide synthesis has been developed. It has been determined that complete 1,2-trans selectivity can be achieved with the use of a 2-O-picolyl moiety, a novel neighboring group that is capable of efficient participation via a six-membered intermediate. The application of the picolyl concept to glycosidations of thioimidoyl, thioglycosyl, and trichloroacetimidoyl glycosyl donors is demonstrated. The picolyl moiety also retains the glycosyl donor in the armed state, as opposed to conventional acyl participating moieties. We name this new approach the inverse armed-disarmed strategy, because it allows for the chemoselective introduction of a 1,2-trans glycosidic linkage prior to other linkages. In the context of the oligosaccharide synthesis, the strategy provides trans-trans and trans-cis patterned oligosaccharides as opposed to classic Fraser-Reid's armed-disarmed approach leading to cis-trans and cis-cis linkages.
Authors
I am an author on this paper
Click your name to claim this paper and add it to your profile.
Reviews
Recommended
No Data Available