Literature DB >> 17580878

IPy2BF4-mediated transformation of n-pentenyl glycosides to glycosyl fluorides: a new pair of semiorthogonal glycosyl donors.

J Cristóbal López1, Clara Uriel, Alejandra Guillamón-Martín, Serafín Valverde, Ana M Gómez.   

Abstract

Bis(pyridinium) iodonium(I) tetrafluoroborate (IPy2BF4), a solid and stable reagent, can be used to transform n-pentenyl orthoesters (NPOEs) and n-pentenyl glycosides (NPGs) into glycosyl fluorides. The latter pair constitutes a new set of semiorthogonal glycosyl donors that can be used in glycosylation strategies, alone or in combination with NPOEs.

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Year:  2007        PMID： 17580878     DOI： 10.1021/ol070753r

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


  10 in total

Review 1.  Automated Chemical Oligosaccharide Synthesis: Novel Approach to Traditional Challenges.

Authors:  Matteo Panza; Salvatore G Pistorio; Keith J Stine; Alexei V Demchenko
Journal:  Chem Rev       Date:  2018-06-28       Impact factor: 60.622

Review 2.  Expeditious oligosaccharide synthesis via selective, semi-orthogonal, and orthogonal activation.

Authors:  Sophon Kaeothip; Alexei V Demchenko
Journal:  Carbohydr Res       Date:  2011-05-18       Impact factor: 2.104

3.  S-Benzimidazolyl (SBiz) Imidates as a Platform for Oligosaccharide Synthesis via Active-Latent, Armed-Disarmed, Selective, and Orthogonal Activations.

Authors:  Scott J Hasty; Mithila D Bandara; Nigam P Rath; Alexei V Demchenko
Journal:  J Org Chem       Date:  2017-02-07       Impact factor: 4.354

4.  On orthogonal and selective activation of glycosyl thioimidates and thioglycosides: application to oligosaccharide assembly.

Authors:  Sophon Kaeothip; Alexei V Demchenko
Journal:  J Org Chem       Date:  2011-08-17       Impact factor: 4.354

5.  In situ preactivation strategies for the expeditious synthesis of oligosaccharides: A review.

Authors:  Samantha K Bouhall; Steven J Sucheck
Journal:  J Carbohydr Chem       Date:  2014-01-01       Impact factor: 1.667

6.  Blue Light Photocatalytic Glycosylation without Electrophilic Additives.

Authors:  Peng Wen; David Crich
Journal:  Org Lett       Date:  2017-04-24       Impact factor: 6.005

7.  Application of the superarmed glycosyl donor to chemoselective oligosaccharide synthesis.

Authors:  Laurel K Mydock; Alexei V Demchenko
Journal:  Org Lett       Date:  2008-05-01       Impact factor: 6.005

8.  Unexpected orthogonality of S-benzoxazolyl and S-thiazolinyl glycosides: application to expeditious oligosaccharide assembly.

Authors:  Sophon Kaeothip; Papapida Pornsuriyasak; Nigam P Rath; Alexei V Demchenko
Journal:  Org Lett       Date:  2009-02-19       Impact factor: 6.005

9.  2-Allylphenyl glycosides as complementary building blocks for oligosaccharide and glycoconjugate synthesis.

Authors:  Hemali D Premathilake; Alexei V Demchenko
Journal:  Beilstein J Org Chem       Date:  2012-04-18       Impact factor: 2.883

10.  Counterion influence on the N-I-N halogen bond.

Authors:  Michele Bedin; Alavi Karim; Marcus Reitti; Anna-Carin C Carlsson; Filip Topić; Mario Cetina; Fangfang Pan; Vaclav Havel; Fatima Al-Ameri; Vladimir Sindelar; Kari Rissanen; Jürgen Gräfenstein; Máté Erdélyi
Journal:  Chem Sci       Date:  2015-04-20       Impact factor: 9.825
  10 in total

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