Literature DB >> 18447362

Application of the superarmed glycosyl donor to chemoselective oligosaccharide synthesis.

Laurel K Mydock1, Alexei V Demchenko.   

Abstract

Recently, we discovered a novel method for "superarming" glycosyl donors. Herein, this concept has been exemplified in one-pot oligosaccharide syntheses, whereby the superarmed glycosyl donor was chemoselectively activated over traditional "armed" and disarmed glycosyl acceptors. Direct side-by-side comparison of the reactivities of the classic armed and superarmed glycosyl donors further validates the credibility of the novel concept.

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Year:  2008        PMID： 18447362      PMCID： PMC3150464          DOI： 10.1021/ol800648d

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


  21 in total

1.  Some implications in carbohydrate chemistry of theories relating to the mechanisms of replacement reactions.

Authors:  R U LEMIEUX
Journal:  Adv Carbohydr Chem       Date:  1954

2.  Development of an arming participating group for stereoselective glycosylation and chemoselective oligosaccharide synthesis.

Authors:  James T Smoot; Papapida Pornsuriyasak; Alexei V Demchenko
Journal:  Angew Chem Int Ed Engl       Date:  2005-11-04       Impact factor: 15.336

Review 3.  Chemistry in living systems.

Authors:  Jennifer A Prescher; Carolyn R Bertozzi
Journal:  Nat Chem Biol       Date:  2005-06       Impact factor: 15.040

4.  Synthesis of glycosyl phosphates from 1,2-orthoesters and application to in situ glycosylation reactions.

Authors:  Alessandra Ravidà; Xinyu Liu; Linda Kovacs; Peter H Seeberger
Journal:  Org Lett       Date:  2006-04-27       Impact factor: 6.005

Review 5.  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

6.  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

7.  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

8.  Synthesis of the core tetrasaccharide of Trypanosoma cruzi glycoinositolphospholipids: Manp(alpha1-->6)-Manp(alpha1-->4)-6-(2-aminoethylphosphonic acid)-GlcNp(alpha1-->6)-myo-Ins-1-PO4.

Authors:  Markus Hederos; Peter Konradsson
Journal:  J Org Chem       Date:  2005-09-02       Impact factor: 4.354

9.  One-pot synthesis of sialo-containing glycosyl amino acids by use of an N-trichloroethoxycarbonyl-beta-thiophenyl sialoside.

Authors:  Hiroshi Tanaka; Masaatsu Adachi; Takashi Takahashi
Journal:  Chemistry       Date:  2005-01-21       Impact factor: 5.236

Review 10.  Thioglycosides in sequential glycosylation strategies.

Authors:  Jeroen D C Codée; Remy E J N Litjens; Leendert J van den Bos; Herman S Overkleeft; Gijsbert A van der Marel
Journal:  Chem Soc Rev       Date:  2005-07-27       Impact factor: 54.564
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  16 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.  Installation of electron-donating protective groups, a strategy for glycosylating unreactive thioglycosyl acceptors using the preactivation-based glycosylation method.

Authors:  Youlin Zeng; Zhen Wang; Dennis Whitfield; Xuefei Huang
Journal:  J Org Chem       Date:  2008-09-23       Impact factor: 4.354

3.  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

4.  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 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.  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

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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