Literature DB >> 17134267

Efficient synthesis of a C-analogue of the immunogenic bacterial glycolipid BbGL2.

Suvarn S Kulkarni1, Jacquelyn Gervay-Hague.   

Abstract

Synthesis of a C-analogue of bacterial glycolipid BbGL2 is reported using Grignard reaction of in situ generated beta-galactosyl iodide and subsequent olefin cross metathesis reaction of C-vinyl galactoside as key steps. [reaction: see text]

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Year:  2006        PMID： 17134267     DOI： 10.1021/ol062354m

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


  10 in total

1.  One-pot syntheses of immunostimulatory glycolipids.

Authors:  Matthew Schombs; Francine E Park; Wenjun Du; Suvarn S Kulkarni; Jacquelyn Gervay-Hague
Journal:  J Org Chem       Date:  2010-08-06       Impact factor: 4.354

2.  Application of silver N-heterocyclic carbene complexes in O-glycosidation reactions.

Authors:  Ian J Talisman; Vineet Kumar; Jeffrey R Deschamps; Mark Frisch; Sanjay V Malhotra
Journal:  Carbohydr Res       Date:  2011-08-02       Impact factor: 2.104

3.  Two-step functionalization of oligosaccharides using glycosyl iodide and trimethylene oxide and its applications to multivalent glycoconjugates.

Authors:  Hsiao-Wu Hsieh; Ryan A Davis; Jessica A Hoch; Jacquelyn Gervay-Hague
Journal:  Chemistry       Date:  2014-04-08       Impact factor: 5.236

4.  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

5.  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

Review 6.  Synthesis and Glycosidation of Anomeric Halides: Evolution from Early Studies to Modern Methods of the 21st Century.

Authors:  Yashapal Singh; Scott A Geringer; Alexei V Demchenko
Journal:  Chem Rev       Date:  2022-06-08       Impact factor: 72.087

7.  Synthesis of β-C-galactosyl D- and L-alanines.

Authors:  V Narasimharao Thota; Jacquelyn Gervay-Hague; Suvarn S Kulkarni
Journal:  Org Biomol Chem       Date:  2012-10-28       Impact factor: 3.876

8.  Two-step synthesis of the immunogenic bacterial glycolipid BbGL1.

Authors:  Suvarn S Kulkarni; Jacquelyn Gervay-Hague
Journal:  Org Lett       Date:  2008-09-18       Impact factor: 6.005

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

Authors:  Ernest G Nolen; Leyan Li; Kristopher V Waynant
Journal:  J Org Chem       Date:  2013-06-17       Impact factor: 4.354

10.  Integrating ReSET with glycosyl iodide glycosylation in step-economy syntheses of tumor-associated carbohydrate antigens and immunogenic glycolipids.

Authors:  Hsiao-Wu Hsieh; Matthew W Schombs; Jacquelyn Gervay-Hague
Journal:  J Org Chem       Date:  2014-02-07       Impact factor: 4.354
  10 in total

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