Literature DB >> 21919522

Methodology development and physical organic chemistry: a powerful combination for the advancement of glycochemistry.

David Crich1.   

Abstract

This Perspective outlines work in the Crich group on the diastereoselective synthesis of the so-called difficult classes of glycosidic bond: the 2-deoxy-β-glycopyranosides, the β-mannopyranosides, the α-sialosides, the α-glucopyranosides, and the β-arabinofuranosides with an emphasis on the critical interplay between mechanism and methodology development.

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Year:  2011        PMID： 21919522      PMCID： PMC3215858          DOI： 10.1021/jo2017026

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


  152 in total

1.  Why are the hydroxy groups of partially protected N-acetylglucosamine derivatives such poor glycosyl acceptors, and what can be done about it? A comparative study of the reactivity of N-acetyl-, N-phthalimido-, and 2-azido-2-deoxy-glucosamine derivatives in glycosylation. 2-Picolinyl ethers as reactivity-enhancing replacements for benzyl ethers.

Authors:  D Crich; V Dudkin
Journal:  J Am Chem Soc       Date:  2001-07-18       Impact factor: 15.419

2.  Efficient, diastereoselective chemical synthesis of a beta-mannopyranosyl phosphoisoprenoid.

Authors:  D Crich; V Dudkin
Journal:  Org Lett       Date:  2000-11-30       Impact factor: 6.005

3.  1-Benzenesulfinyl piperidine/trifluoromethanesulfonic anhydride: a potent combination of shelf-stable reagents for the low-temperature conversion of thioglycosides to glycosyl triflates and for the formation of diverse glycosidic linkages.

Authors:  D Crich; M Smith
Journal:  J Am Chem Soc       Date:  2001-09-19       Impact factor: 15.419

4.  2-(Hydroxycarbonyl)benzyl glycosides: a novel type of glycosyl donors for highly efficient beta-mannopyranosylation and oligosaccharide synthesis by latent-active glycosylation.

Authors:  K S Kim; J H Kim; Y J Lee; Y J Lee; J Park
Journal:  J Am Chem Soc       Date:  2001-09-05       Impact factor: 15.419

5.  A stereoselective approach for the synthesis of alpha-sialosides.

Authors:  C D Meo; A V Demchenko; G J Boons
Journal:  J Org Chem       Date:  2001-08-10       Impact factor: 4.354

6.  Solvolyses of 2-Deoxy-alpha- and beta-D-Glucopyranosyl 4'-Bromoisoquinolinium Tetrafluoroborates.

Authors: 
Journal:  J Org Chem       Date:  2000-07-14       Impact factor: 4.354

7.  The Thioglycoside and Glycosyl Phosphite of 5-Azido Sialic Acid: Excellent Donors for the alpha-Glycosylation of Primary Hydroxy Groups This research was supported by Academia Sinica (Taipei) and the NIH (USA).

Authors:  Chung-Shan Yu; Kenichi Niikura; Chun-Cheng Lin; Chi-Huey Wong
Journal:  Angew Chem Int Ed Engl       Date:  2001-08-03       Impact factor: 15.336

8.  S-(4-methoxyphenyl) benzenethiosulfinate (MPBT)/trifluoromethanesulfonic anhydride: a convenient system for the generation of glycosyl triflates from thioglycosides.

Authors:  D Crich; M Smith
Journal:  Org Lett       Date:  2000-12-14       Impact factor: 6.005

9.  Direct stereoselective synthesis of beta-thiomannosides.

Authors:  D Crich; H Li
Journal:  J Org Chem       Date:  2000-02-11       Impact factor: 4.354

10.  Highly diastereoselective alpha-mannopyranosylation in the absence of participating protecting groups.

Authors:  D Crich; W Cai; Z Dai
Journal:  J Org Chem       Date:  2000-03-10       Impact factor: 4.354
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  23 in total

1.  Immobilization of glycans on solid surfaces for application in glycomics.

Authors:  Crystal L O'Neil; Keith J Stine; Alexei V Demchenko
Journal:  J Carbohydr Chem       Date:  2018-04-27       Impact factor: 1.667

Review 2.  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 3.  Oligosaccharide Synthesis and Translational Innovation.

Authors:  Larissa Krasnova; Chi-Huey Wong
Journal:  J Am Chem Soc       Date:  2019-02-18       Impact factor: 15.419

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

5.  Influence of protecting groups on the anomeric equilibrium; case of the 4,6-O-benzylidene acetal in the mannopyranose series.

Authors:  Indrajeet Sharma; Luis Bohé; David Crich
Journal:  Carbohydr Res       Date:  2012-06-07       Impact factor: 2.104

6.  Regenerative Glycosylation.

Authors:  Yashapal Singh; Tinghua Wang; Scott A Geringer; Keith J Stine; Alexei V Demchenko
Journal:  J Org Chem       Date:  2017-12-22       Impact factor: 4.354

7.  Regenerative glycosylation under nucleophilic catalysis.

Authors:  Swati S Nigudkar; Keith J Stine; Alexei V Demchenko
Journal:  J Am Chem Soc       Date:  2014-01-09       Impact factor: 15.419

8.  Synthesis and Stereocontrolled Equatorially Selective Glycosylation Reactions of a Pseudaminic Acid Donor: Importance of the Side-Chain Conformation and Regioselective Reduction of Azide Protecting Groups.

Authors:  Bibek Dhakal; David Crich
Journal:  J Am Chem Soc       Date:  2018-10-25       Impact factor: 15.419

9.  Influence of side chain conformation and configuration on glycosyl donor reactivity and selectivity as illustrated by sialic acid donors epimeric at the 7-position.

Authors:  Pavan K Kancharla; David Crich
Journal:  J Am Chem Soc       Date:  2013-12-09       Impact factor: 15.419

10.  Determination of the Influence of Side-Chain Conformation on Glycosylation Selectivity using Conformationally Restricted Donors.

Authors:  Suresh Dharuman; David Crich
Journal:  Chemistry       Date:  2016-02-16       Impact factor: 5.236
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