Literature DB >> 20104917

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

Hemali D Premathilake1, Laurel K Mydock, Alexei V Demchenko.   

Abstract

A complementary concept for superarming glycosyl donors through the use of common protecting groups was previously discovered with S-benzoxazolyl (SBox) glycosyl donors. As this strategy can be of benefit to existing oligosaccharide methodologies, it has now been expanded to encompass a wide array of common, stable glycosyl donors. The versatility of this developed technique has been further illustrated in application to a sequential chemoselective oligosaccharide synthesis, wherein a superarmed ethyl thioglycoside was incorporated into the conventional armed-disarmed strategy.

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Year:  2010        PMID: 20104917      PMCID: PMC2827031          DOI: 10.1021/jo9021474

Source DB:  PubMed          Journal:  J Org Chem        ISSN: 0022-3263            Impact factor:   4.354


  20 in total

1.  The disarming effect of the 4,6-acetal group on glycoside reactivity: torsional or electronic?

Authors:  Henrik Helligsø Jensen; Lars Ulrik Nordstrøm; Mikael Bols
Journal:  J Am Chem Soc       Date:  2004-08-04       Impact factor: 15.419

2.  Versatile synthesis and mechanism of activation of S-benzoxazolyl glycosides.

Authors:  Medha N Kamat; Nigam P Rath; Alexei V Demchenko
Journal:  J Org Chem       Date:  2007-08-04       Impact factor: 4.354

3.  Synthesis of Oligosaccharide Structures from the Lipopolysaccharide of Moraxella catarrhalis.

Authors:  Kerstin Ekelöf; Stefan Oscarson
Journal:  J Org Chem       Date:  1996-11-01       Impact factor: 4.354

Review 4.  Going to extremes: "super" armed glycosyl donors in glycosylation chemistry.

Authors:  Henrik H Jensen; Christian Marcus Pedersen; Mikael Bols
Journal:  Chemistry       Date:  2007       Impact factor: 5.236

5.  S-thiazolinyl (STaz) glycosides as versatile building blocks for convergent selective, chemoselective, and orthogonal oligosaccharide synthesis.

Authors:  Papapida Pornsuriyasak; Alexei V Demchenko
Journal:  Chemistry       Date:  2006-08-25       Impact factor: 5.236

6.  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

7.  Sulfide-mediated dehydrative glycosylation.

Authors:  H M Nguyen; Y Chen; S G Duron; D Y Gin
Journal:  J Am Chem Soc       Date:  2001-09-12       Impact factor: 15.419

8.  New principles for glycoside-bond formation.

Authors:  Xiangming Zhu; Richard R Schmidt
Journal:  Angew Chem Int Ed Engl       Date:  2009       Impact factor: 15.336

9.  Stereoselective synthesis of allyl-C-mannosyl compounds: use of a temporary silicon connection in intramolecular allylation strategies with allylsilanes.

Authors:  Julien Beignet; James Tiernan; Chang H Woo; Benson M Kariuki; Liam R Cox
Journal:  J Org Chem       Date:  2004-09-17       Impact factor: 4.354

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

Authors:  David Crich; Ming Li
Journal:  Org Lett       Date:  2007-09-22       Impact factor: 6.005

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  14 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

2.  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

3.  Comparison of the armed/disarmed building blocks of the D-gluco and D-glucosamino series in the context of chemoselective oligosaccharide synthesis.

Authors:  Teerada Kamkhachorn; Archana R Parameswar; Alexei V Demchenko
Journal:  Org Lett       Date:  2010-07-02       Impact factor: 6.005

4.  Direct synthesis of diastereomerically pure glycosyl sulfonium salts.

Authors:  Laurel K Mydock; Medha N Kamat; Alexei V Demchenko
Journal:  Org Lett       Date:  2011-05-12       Impact factor: 6.005

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.  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

7.  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

8.  S-Benzimidazolyl glycosides as a platform for oligosaccharide synthesis by an active-latent strategy.

Authors:  Scott J Hasty; Matthew A Kleine; Alexei V Demchenko
Journal:  Angew Chem Int Ed Engl       Date:  2011-03-23       Impact factor: 15.336

9.  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

10.  Conformationally superarmed S-ethyl glycosyl donors as effective building blocks for chemoselective oligosaccharide synthesis in one pot.

Authors:  Mithila D Bandara; Jagodige P Yasomanee; Nigam P Rath; Christian M Pedersen; Mikael Bols; Alexei V Demchenko
Journal:  Org Biomol Chem       Date:  2017-01-18       Impact factor: 3.876

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