Literature DB >> 17887763

Revisiting the armed-disarmed concept: the importance of anomeric configuration in the activation of S-benzoxazolyl glycosides.

David Crich1, Ming Li.   

Abstract

The unexpectedly high reactivity of a (2-benzoxazolyl) per-O-benzoyl-beta-D-thioglucoside and related donors in reactions promoted by copper(II) trifluoromethanesulfonate is revealed, by comparison with the unreactive alpha-anomer, to be the result of neighboring group participation. Revision of the armed-disarmed concept for glycosyl donors is not required.

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Year:  2007        PMID： 17887763      PMCID： PMC3221596          DOI： 10.1021/ol701466u

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


  2 in total

Review 1.  Synthesis and reactions of glycosides.

Authors:  Per J Garegg
Journal:  Adv Carbohydr Chem Biochem       Date:  2004       Impact factor: 12.200

2.  Revisiting the armed-disarmed concept rationale: s-benzoxazolyl glycosides in chemoselective oligosaccharide synthesis.

Authors:  Medha N Kamat; Alexei V Demchenko
Journal:  Org Lett       Date:  2005-07-21       Impact factor: 6.005
  2 in total
  16 in total

1.  Glycal assembly by the in situ generation of glycosyl dithiocarbamates.

Authors:  Panuwat Padungros; Laura Alberch; Alexander Wei
Journal:  Org Lett       Date:  2012-06-11       Impact factor: 6.005

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

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

3.  Mechanisms of Stereodirecting Participation and Ester Migration from Near and Far in Glycosylation and Related Reactions.

Authors:  Asiri A Hettikankanamalage; Robert Lassfolk; Filip S Ekholm; Reko Leino; David Crich
Journal:  Chem Rev       Date:  2020-07-05       Impact factor: 60.622

Review 4.  The Experimental Evidence in Support of Glycosylation Mechanisms at the SN1-SN2 Interface.

Authors:  Philip Ouma Adero; Harsha Amarasekara; Peng Wen; Luis Bohé; David Crich
Journal:  Chem Rev       Date:  2018-05-30       Impact factor: 60.622

Review 5.  Superarmed and superdisarmed building blocks in expeditious oligosaccharide synthesis.

Authors:  Hemali D Premathilake; Alexei V Demchenko
Journal:  Top Curr Chem       Date:  2011

6.  Superarming of glycosyl donors by combined neighboring and conformational effects.

Authors:  Mads Heuckendorff; Hemali D Premathilake; Papapida Pornsuriyasak; Anders Ø Madsen; Christian M Pedersen; Mikael Bols; Alexei V Demchenko
Journal:  Org Lett       Date:  2013-09-05       Impact factor: 6.005

7.  Glycosyl Thioimidates as Versatile Building Blocks for Organic Synthesis.

Authors:  S J Hasty; A V Demchenko
Journal:  Chem Heterocycl Compd (N Y)       Date:  2012-04       Impact factor: 1.277

8.  Does neighboring group participation by non-vicinal esters play a role in glycosylation reactions? Effective probes for the detection of bridging intermediates.

Authors:  David Crich; Tianshun Hu; Feng Cai
Journal:  J Org Chem       Date:  2008-10-22       Impact factor: 4.354

9.  Superarming common glycosyl donors by simple 2-O-benzoyl-3,4,6-tri-O-benzyl protection.

Authors:  Hemali D Premathilake; Laurel K Mydock; Alexei V Demchenko
Journal:  J Org Chem       Date:  2010-02-19       Impact factor: 4.354

10.  Erosion of stereochemical control with increasing nucleophilicity: O-glycosylation at the diffusion limit.

Authors:  Matthew G Beaver; K A Woerpel
Journal:  J Org Chem       Date:  2010-02-19       Impact factor: 4.354
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