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Literature DB >> 15496103

Efficient synthesis of alpha-C-galactosyl ceramide immunostimulants: use of ethylene-promoted olefin cross-metathesis.

Guangwu Chen¹, John Schmieg, Moriya Tsuji, Richard W Franck.

Abstract

[reaction: see text] Olefin cross-metathesis has been used to prepare alpha-C-galactosylceramide derivatives. The metathesis process merged vinyl and propenyl glycosides with vinyl derivatives of phytosphingosine. The use of ethylene enhanced the yield of the methathesis step.

Entities: Chemical

Mesh：

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Year: 2004 PMID： 15496103 DOI： 10.1021/ol0482137

Source DB: PubMed Journal: Org Lett ISSN： 1523-7052 Impact factor: 6.005

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Cited

16 in total

1. C-Galactosylceramide: Synthesis and Immunology.

Authors: Richard W Franck
Journal: C R Chim Date: 2012-01-01 Impact factor: 3.117

2. Total synthesis of α-1C-galactosylceramide, an immunostimulatory C-glycosphingolipid, and confirmation of the stereochemistry in the first-generation synthesis.

Authors: Zheng Liu; Hoe-Sup Byun; Robert Bittman
Journal: J Org Chem Date: 2011-10-04 Impact factor: 4.354

3. Multiple innate signaling pathways cooperate with CD40 to induce potent, CD70-dependent cellular immunity.

Authors: Jennifer A McWilliams; Phillip J Sanchez; Catherine Haluszczak; Laurent Gapin; Ross M Kedl
Journal: Vaccine Date: 2009-12-06 Impact factor: 3.641

4. A Solvent-free Approach to Glycosyl Amides: Towards the Synthesis of α-N-Galactosyl Ceramides.

Authors: Divya Chennamadhavuni; Amy R Howell
Journal: Tetrahedron Lett Date: 2015-06-03 Impact factor: 2.415

5. Synthesis of C-glycoside analogues of α-galactosylceramide via linear allylic C-H oxidation and allyl cyanate to isocyanate rearrangement.

Authors: Zheng Liu; Robert Bittman
Journal: Org Lett Date: 2012-01-10 Impact factor: 6.005

6. Synthesis of immunostimulatory alpha-C-galactosylceramide glycolipids via Sonogashira coupling, asymmetric epoxidation, and trichloroacetimidate-mediated epoxide opening.

Authors: Zheng Liu; Hoe-Sup Byun; Robert Bittman
Journal: Org Lett Date: 2010-07-02 Impact factor: 6.005

Efficient synthesis of alpha-C-galactosyl ceramide immunostimulants: use of ethylene-promoted olefin cross-metathesis.

1. C-Galactosylceramide: Synthesis and Immunology.

2. Total synthesis of α-1C-galactosylceramide, an immunostimulatory C-glycosphingolipid, and confirmation of the stereochemistry in the first-generation synthesis.

3. Multiple innate signaling pathways cooperate with CD40 to induce potent, CD70-dependent cellular immunity.

4. A Solvent-free Approach to Glycosyl Amides: Towards the Synthesis of α-N-Galactosyl Ceramides.

5. Synthesis of C-glycoside analogues of α-galactosylceramide via linear allylic C-H oxidation and allyl cyanate to isocyanate rearrangement.

6. Synthesis of immunostimulatory alpha-C-galactosylceramide glycolipids via Sonogashira coupling, asymmetric epoxidation, and trichloroacetimidate-mediated epoxide opening.

7. Mechanisms for glycolipid antigen-driven cytokine polarization by Valpha14i NKT cells.

8. Potent immune-modulating and anticancer effects of NKT cell stimulatory glycolipids.

9. Synthesis of β-C-GlcNAc Ser from β-C-Glc Ser.

10. C-Galactosylceramide Diastereomers via Sharpless Asymmetric Epoxidation Chemistry.