Literature DB >> 16100617

Thioglycosides in sequential glycosylation strategies.

Jeroen D C Codée1, Remy E J N Litjens, Leendert J van den Bos, Herman S Overkleeft, Gijsbert A van der Marel.   

Abstract

This tutorial review surveys the use of thioglycosides in the development of sequential glycosylation methodologies, with a focus on chemoselective, orthogonal and iterative glycosylation strategies reported since the beginning of this century. Both fundamental aspects of glycosidic bond formation and ingenious state-of-the-art methodologies are presented.

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Year:  2005        PMID: 16100617     DOI: 10.1039/b417138c

Source DB:  PubMed          Journal:  Chem Soc Rev        ISSN: 0306-0012            Impact factor:   54.564


  47 in total

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3.  Installation of electron-donating protective groups, a strategy for glycosylating unreactive thioglycosyl acceptors using the preactivation-based glycosylation method.

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4.  Superarming the S-benzoxazolyl glycosyl donors by simple 2-O-benzoyl-3,4,6-tri-O-benzyl protection.

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6.  Stereoselective assembly of complex oligosaccharides using anomeric sulfonium ions as glycosyl donors.

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Journal:  J Am Chem Soc       Date:  2012-04-18       Impact factor: 15.419

7.  On the influence of the C2-O2 and C3-O3 bonds in 4,6-O-benzylidene-directed beta-mannopyranosylation and alpha-glucopyranosylation.

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Journal:  J Org Chem       Date:  2006-10-27       Impact factor: 4.354

8.  Rapid assembly of oligosaccharides: a highly convergent strategy for the assembly of a glycosylated amino acid derived from PSGL-1.

Authors:  Yusuf Vohra; Therese Buskas; Geert-Jan Boons
Journal:  J Org Chem       Date:  2009-08-21       Impact factor: 4.354

9.  Chiral-auxiliary-mediated 1,2-cis-glycosylations for the solid-supported synthesis of a biologically important branched alpha-glucan.

Authors:  Thomas J Boltje; Jin-Hwan Kim; Jin Park; Geert-Jan Boons
Journal:  Nat Chem       Date:  2010-05-23       Impact factor: 24.427

10.  Assembly of a Complex Branched Oligosaccharide by Combining Fluorous-Supported Synthesis and Stereoselective Glycosylations using Anomeric Sulfonium Ions.

Authors:  Wei Huang; Qi Gao; Geert-Jan Boons
Journal:  Chemistry       Date:  2015-08-06       Impact factor: 5.236

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