Literature DB >> 18447363

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

Laurel K Mydock1, Alexei V Demchenko.   

Abstract

The strategic placement of common protecting groups led to the discovery of a new method for "superarming" glycosyl donors. Conceptualized from our previous studies on the O-2/O-5 Cooperative Effect, it was determined that S-benzoxazolyl glycosyl donors possessing both a participating moiety at C-2 and an electronically armed lone pair at O-5, such as the superarmed glycosyl donor shown above, were exceptionally reactive.

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Year:  2008        PMID： 18447363      PMCID： PMC3146391          DOI： 10.1021/ol800345j

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


  22 in total

1.  Diisobutylaluminum-Promoted Regioselective De-O-benzylation of Perbenzylated Cyclodextrins: A Powerful New Strategy for the Preparation of Selectively Modified Cyclodextrins The authors thank the European Community for a TMR Marie Curie Research Training Grant (no. ERBFMBICT983225) to A.J.P.

Authors: 
Journal:  Angew Chem Int Ed Engl       Date:  2000-10-16       Impact factor: 15.336

2.  Synthesis of di-branched heptasaccharide by one-pot glycosylation using seven independent building blocks.

Authors:  Hiroshi Tanaka; Masaatsu Adachi; Hirokazu Tsukamoto; Takeji Ikeda; Haruo Yamada; Takashi Takahashi
Journal:  Org Lett       Date:  2002-11-28       Impact factor: 6.005

3.  Iterative one-pot synthesis of oligosaccharides.

Authors:  Xuefei Huang; Lijun Huang; Haisheng Wang; Xin-Shan Ye
Journal:  Angew Chem Int Ed Engl       Date:  2004-10-04       Impact factor: 15.336

4.  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

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.  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.  Ph2SO/Tf2O: a powerful promotor system in chemoselective glycosylations using thioglycosides.

Authors:  Jeroen D C Codée; Remy E J N Litjens; René den Heeten; Herman S Overkleeft; Jacques H van Boom; Gijs A van der Marel
Journal:  Org Lett       Date:  2003-05-01       Impact factor: 6.005

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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  24 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.  HPLC-assisted automated oligosaccharide synthesis.

Authors:  N Vijaya Ganesh; Kohki Fujikawa; Yih Horng Tan; Keith J Stine; Alexei V Demchenko
Journal:  Org Lett       Date:  2012-05-30       Impact factor: 6.005

Review 3.  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

4.  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

5.  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

6.  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

Review 7.  Superarmed and superdisarmed building blocks in expeditious oligosaccharide synthesis.

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

8.  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

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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