Synthesis of α-s-glycosphingolipids based on uronic acids

Ciaran O'Reilly; Paul V. Murphy

doi:10.1021/ol202042h

Synthesis of α-s-glycosphingolipids based on uronic acids

Ciaran O'Reilly, Paul V. Murphy

Infectious Disease

Research output: Contribution to a Journal (Peer & Non Peer) › Article › peer-review

28 Citations (Scopus)

Abstract

The synthesis of S-glycosphingolipids based on uronic acids is described. These compounds are analogous to the highly immunostimulatory antigens isolated from the cell walls of bacteria of the Sphingomonas family. Key to the synthetic route is a stereoselective anomerization to give α-glycosyl thiol precursors. A route to a sphinganine precursor from pseudoephedrine glycinamide is also described.

Original language	English
Pages (from-to)	5168-5171
Number of pages	4
Journal	Organic Letters
Volume	13
Issue number	19
DOIs	https://doi.org/10.1021/ol202042h
Publication status	Published - 7 Oct 2011

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10.1021/ol202042h

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title = "Synthesis of α-s-glycosphingolipids based on uronic acids",

abstract = "The synthesis of S-glycosphingolipids based on uronic acids is described. These compounds are analogous to the highly immunostimulatory antigens isolated from the cell walls of bacteria of the Sphingomonas family. Key to the synthetic route is a stereoselective anomerization to give α-glycosyl thiol precursors. A route to a sphinganine precursor from pseudoephedrine glycinamide is also described.",

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year = "2011",

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N2 - The synthesis of S-glycosphingolipids based on uronic acids is described. These compounds are analogous to the highly immunostimulatory antigens isolated from the cell walls of bacteria of the Sphingomonas family. Key to the synthetic route is a stereoselective anomerization to give α-glycosyl thiol precursors. A route to a sphinganine precursor from pseudoephedrine glycinamide is also described.

AB - The synthesis of S-glycosphingolipids based on uronic acids is described. These compounds are analogous to the highly immunostimulatory antigens isolated from the cell walls of bacteria of the Sphingomonas family. Key to the synthetic route is a stereoselective anomerization to give α-glycosyl thiol precursors. A route to a sphinganine precursor from pseudoephedrine glycinamide is also described.

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DO - 10.1021/ol202042h

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VL - 13

SP - 5168

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JO - Organic Letters

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Synthesis of α-s-glycosphingolipids based on uronic acids

Abstract

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