ArticleThe Journal of organic chemistry2007
Synthesis of nor-C-linked neuraminic acid disaccharide: a versatile precursor of C-analogs of oligosialic acids and gangliosides.
Article in The Journal of organic chemistry, 2007. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 3 papers.
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The abstract states no effect estimate the extractor could read, or names no intervention and outcome on the map, so this paper lights no cell and moves no belief. It is still indexed, cited and linked below.
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Who cites it
3 citing papers in PubMed, 16 citations in OpenAlex.
- Synthesis of 4-The Journal of organic chemistry · 2021Article
- Synthesis and Biological Evaluation of Non-Hydrolizable 1,2,3-Triazole Linked Sialic Acid Derivatives as Neuraminidase Inhibitors.European journal of organic chemistry · 2009Article
- Stereoselective synthesis of a C-linked neuraminic acid disaccharide: potential building block for the synthesis of C-analogues of polysialic acids.The Journal of organic chemistry · 2008Article
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Authors and funding
3 authors at 1 institution in 1 country.
Funding
Abstract
The Neu5Acalpha(2,8)Neu5Ac disaccharide is an important constituent of tumor related antigen, however, the O-linkage is catabolically unstable. Vaccination with a catabolically stable sialic acid C-glycoside analog might enhance immunogenicity. The synthesis of Neu5Ac nor-C-disaccharide 20R/S, corresponding to versatile precursors of C-analogs of oligosialic acid and gangliosides, is reported. The synthesis of the protected acceptor was not straightforward, as ester, silyl ether, and isopropylidene protection failed to afford desired C-linked disaccharide. Allyl ether protection of hydroxyl groups and acetyl protection of the acetamido facilitated the successful synthesis of the 8-aldehyde neuraminyl acceptor. Samarium mediated C-glycosylation afforded the desired nor-C-disaccharide as a mixture of two separable diastereomers.
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