Lewis Acid Induced Anomerization of Se-Glycosides. Application to Synthesis of alpha-Se-GalCer

Paul Murphy

doi:http://hdl.handle.net/10379/5940

Lewis Acid Induced Anomerization of Se-Glycosides. Application to Synthesis of alpha-Se-GalCer

Paul Murphy

Infectious Disease

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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).

Original language	English (Ireland)
Number of pages	4
Journal	Organic Letters
Volume	18
DOIs	https://doi.org/http://hdl.handle.net/10379/5940
Publication status	Published - 1 Feb 2016

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Authors
McDonagh, AW,Mahon, MF,Murphy, PV

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title = "Lewis Acid Induced Anomerization of Se-Glycosides. Application to Synthesis of alpha-Se-GalCer",

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).",

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year = "2016",

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doi = "http://hdl.handle.net/10379/5940",

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AU - Murphy, Paul

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N2 - 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).

AB - 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).

U2 - http://hdl.handle.net/10379/5940

DO - http://hdl.handle.net/10379/5940

M3 - Article

VL - 18

JO - Organic Letters

JF - Organic Letters

ER -

Lewis Acid Induced Anomerization of Se-Glycosides. Application to Synthesis of alpha-Se-GalCer

Abstract

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