Literature DB >> 19746154

C-Galactosylceramide Diastereomers via Sharpless Asymmetric Epoxidation Chemistry.

Jun Pu1, Richard W Franck.   

Abstract

Entities:  

Year:  2008        PMID： 19746154      PMCID： PMC2631176          DOI： 10.1016/j.tet.2008.06.007

Source DB:  PubMed          Journal:  Tetrahedron        ISSN： 0040-4020            Impact factor:   2.457


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  22 in total

1.  Structure-based discovery of glycolipids for CD1d-mediated NKT cell activation: tuning the adjuvant versus immunosuppression activity.

Authors:  Masakazu Fujio; Douglass Wu; Raquel Garcia-Navarro; David D Ho; Moriya Tsuji; Chi-Huey Wong
Journal:  J Am Chem Soc       Date:  2006-07-19       Impact factor: 15.419

Review 2.  Glycolipids for natural killer T cells.

Authors:  Paul B Savage; Luc Teyton; Albert Bendelac
Journal:  Chem Soc Rev       Date:  2006-06-09       Impact factor: 54.564

3.  Synthesis and evaluation of sphinganine analogues of KRN7000 and OCH.

Authors:  Rachel M Ndonye; Douglas P Izmirian; Matthew F Dunn; Karl O A Yu; Steven A Porcelli; Archana Khurana; Mitchell Kronenberg; Stewart K Richardson; Amy R Howell
Journal:  J Org Chem       Date:  2005-12-09       Impact factor: 4.354

4.  The crystal structure of human CD1d with and without alpha-galactosylceramide.

Authors:  Michael Koch; Victoria S Stronge; Dawn Shepherd; Stephan D Gadola; Bini Mathew; Gerd Ritter; Alan R Fersht; Gurdyal S Besra; Richard R Schmidt; E Yvonne Jones; Vincenzo Cerundolo
Journal:  Nat Immunol       Date:  2005-07-10       Impact factor: 25.606

5.  Expedient synthesis of the alpha-C-glycoside analogue of the immunostimulant galactosylceramide (KRN7000).

Authors:  Peter Wipf; Joshua G Pierce
Journal:  Org Lett       Date:  2006-07-20       Impact factor: 6.005

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

Authors:  Guangwu Chen; John Schmieg; Moriya Tsuji; Richard W Franck
Journal:  Org Lett       Date:  2004-10-28       Impact factor: 6.005

7.  Design and synthesis of a novel class of sugar-peptide hybrids: C-linked glyco beta-amino acids through a stereoselective "acetate" Mannich reaction as the key strategic element.

Authors:  Claudio Palomo; Mikel Oiarbide; Aitor Landa; M Concepción González-Rego; Jesús M García; Alberto González; José M Odriozola; Manuel Martín-Pastor; Anthony Linden
Journal:  J Am Chem Soc       Date:  2002-07-24       Impact factor: 15.419

8.  CD1d-lipid-antigen recognition by the semi-invariant NKT T-cell receptor.

Authors:  Natalie A Borg; Kwok S Wun; Lars Kjer-Nielsen; Matthew C J Wilce; Daniel G Pellicci; Ruide Koh; Gurdyal S Besra; Mandvi Bharadwaj; Dale I Godfrey; James McCluskey; Jamie Rossjohn
Journal:  Nature       Date:  2007-06-20       Impact factor: 49.962

9.  Combined natural killer T-cell based immunotherapy eradicates established tumors in mice.

Authors:  Michele W L Teng; Jennifer A Westwood; Phillip K Darcy; Janelle Sharkey; Moriya Tsuji; Richard W Franck; Steven A Porcelli; Gurdyal S Besra; Kazuyoshi Takeda; Hideo Yagita; Michael H Kershaw; Mark J Smyth
Journal:  Cancer Res       Date:  2007-08-01       Impact factor: 12.701

10.  Rapid identification of immunostimulatory alpha-galactosylceramides using synthetic combinatorial libraries.

Authors:  Qian Li; Rachel M Ndonye; Petr A Illarionov; Karl O A Yu; Elliot S Jerud; Kristine Diaz; Gabriel Bricard; Steven A Porcelli; Gurdyal S Besra; Young-Tae Chang; Amy R Howell
Journal:  J Comb Chem       Date:  2007-09-27
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  11 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.  Asymmetric synthesis of D-ribo-phytosphingosine from 1-tetradecyne and (4-methoxyphenoxy)acetaldehyde.

Authors:  Zheng Liu; Hoe-Sup Byun; Robert Bittman
Journal:  J Org Chem       Date:  2010-07-02       Impact factor: 4.354

3.  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

4.  An organocatalytic strategy for the stereoselective synthesis of C-galactosides with fluorine at the pseudoanomeric carbon.

Authors:  Ahmad S Altiti; S Bachan; W Alrowhani; D R Mootoo
Journal:  Org Biomol Chem       Date:  2015-11-07       Impact factor: 3.876

5.  Synthesis and biological activities of C-glycosides of KRN 7000 with novel ceramide residues.

Authors:  Ahmad S Altiti; Xiaojing Ma; Lixing Zhang; Yi Ban; Richard W Franck; David R Mootoo
Journal:  Carbohydr Res       Date:  2017-03-06       Impact factor: 2.104

6.  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

7.  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

8.  C-glycosphingolipid precursors via iodocyclization of homoallyic trichloroacetimidates.

Authors:  Ahmad S Altiti; David R Mootoo
Journal:  Carbohydr Res       Date:  2015-02-21       Impact factor: 2.104

9.  The Crotylation Way to Glycosphingolipids: Synthesis of Analogues of KRN7000.

Authors:  Ahmad S Altiti; Stewart Bachan; David R Mootoo
Journal:  Org Lett       Date:  2016-08-25       Impact factor: 6.005

10.  Intramolecular nitrogen delivery for the synthesis of C-glycosphingolipids. Application to the C-glycoside of the immunostimulant KRN7000.

Authors:  Ahmad S Altiti; David R Mootoo
Journal:  Org Lett       Date:  2014-02-21       Impact factor: 6.005
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