Thumbnail Image
Item type:Publication,

Lewis acid induced anomerization of se-glycosides. Application to synthesis of alpha-Se-GalCer

McDonagh, Anthony W.
; 
Mahon, Mary F.
; 
Murphy, Paul V.

Files

Thumbnail Image
Org_Lett_Revised_Manuscript.pdf
Adobe PDF, 830.15 KB

Citations

Altmetric

item.page.identifiers

http://hdl.handle.net/10379/5940
 https://doi.org/10.13025/15043

Date

2016-01-22

Keywords

School of Biological and Chemical Sciences , Killer t-cells , X-ray crystallography , Glucuronic acid , Stereoselective synthesis , Thioglycoside analog , Efficient synthesis , Protecting group , Glycosyl donors , Facile method , C-arylation

item.page.type

journal article

item.page.downloads

Citation

McDonagh, Anthony W., Mahon, Mary F., & Murphy, Paul V. (2016). Lewis Acid Induced Anomerization of Se-Glycosides. Application to Synthesis of α-Se-GalCer. Organic Letters, 18(3), 552-555. doi: 10.1021/acs.orglett.5b03591

Abstract

The TiCl4 induced anomerization of selenium glycosides of galacturonic acid derivatives is reported. The reaction was successful for galacturonic acid when various alkyl, alkenyl, alkynyl, saccharide, steroid, and lipid groups were attached to the anomeric Se atom. An increased amount of TiCl4 and/or higher temperature were needed to ensure completion of the reaction in some cases. Yields were higher for reactions carried out at higher dilution. The reaction was applied to the synthesis of Se-based mimics of the potent immunostimulant alpha-GalCer (KRN7000).

item.page.funder

Publisher

American Chemical Society

item.page.publisherdoi

License

CC BY-NC-ND

cbn

Collections

Publications