Literature DB >> 22233351

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

Zheng Liu1, Robert Bittman.   

Abstract

C-Glycoside analogues of α-galactosylceramide were synthesized in which several significant modifications known to promote Th-1 cytokine production were included. The key transformations include C-H oxidation, Sharpless asymmetric epoxidation, olefin cross metathesis, and an allyl cyanate to isocyanate rearrangement.
© 2012 American Chemical Society

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Year:  2012        PMID： 22233351      PMCID： PMC3263403          DOI： 10.1021/ol2032448

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


  22 in total

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3.  Asymmetric synthesis of the cytotoxic marine natural product (+)-awajanomycin and its C-11 epimer.

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Review 4.  Toward an understanding of NKT cell biology: progress and paradoxes.

Authors:  Mitchell Kronenberg
Journal:  Annu Rev Immunol       Date:  2005       Impact factor: 28.527

5.  A phase I study of the natural killer T-cell ligand alpha-galactosylceramide (KRN7000) in patients with solid tumors.

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Journal:  Clin Cancer Res       Date:  2002-12       Impact factor: 12.531

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

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8.  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

9.  A sulfoxide-promoted, catalytic method for the regioselective synthesis of allylic acetates from monosubstituted olefins via C-H oxidation.

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Journal:  J Med Chem       Date:  2009-08-13       Impact factor: 7.446
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  7 in total

1.  The Reaction of β,γ-Epoxy Alcohols with Titanium(III) Reagents. A Proposed Role for Intramolecular Hydrogen Bonding.

Authors:  Sven Klare; Jonathan P Gordon; Andreas Gansäuer; T V RajanBabu; William A Nugent
Journal:  Tetrahedron       Date:  2019-10-01       Impact factor: 2.457

2.  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

3.  Oxidation of Hindered Allylic C-H Bonds with Applications to the Functionalization of Complex Molecules.

Authors:  Zachary C Litman; Ankit Sharma; John F Hartwig
Journal:  ACS Catal       Date:  2017-01-30       Impact factor: 13.084

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Authors:  Zheng Liu; Amy N Courtney; Leonid S Metelitsa; Robert Bittman
Journal:  Chembiochem       Date:  2012-07-10       Impact factor: 3.164

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

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Journal:  Carbohydr Res       Date:  2015-02-21       Impact factor: 2.104

6.  Mild Cu(OTf)2-Mediated C-Glycosylation with Chelation-Assisted Picolinate as a Leaving Group.

Authors:  Wenjing Ye; Christopher M Stevens; Peng Wen; Christopher J Simmons; Weiping Tang
Journal:  J Org Chem       Date:  2020-08-05       Impact factor: 4.354

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

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Journal:  Org Lett       Date:  2014-02-21       Impact factor: 6.005
  7 in total

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