Literature DB >> 22976809

Dissecting the influence of oxazolidinones and cyclic carbonates in sialic acid chemistry.

Pavan K Kancharla1, Chandrasekhar Navuluri, David Crich.   

Abstract

At a moment's notice: Thermal equilibration of 1 and mass spectral analysis of sialyl phosphates suggest that the 4O,5N-oxazolidinone and the 4,5-O-carbonate systems influence the anomeric effect and the mechanisms of sialidation by virtue of their dipole moment in the mean plane of the pyranose ring. The electron-withdrawing effect destabilizes 2 and promotes associative glycosylation mechanisms. TEMPO = 2,2,6,6-tetramethylpiperidine N-oxide.
Copyright © 2012 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

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Year:  2012        PMID： 22976809      PMCID： PMC3489474          DOI： 10.1002/anie.201204400

Source DB:  PubMed          Journal:  Angew Chem Int Ed Engl        ISSN： 1433-7851            Impact factor:   15.336


  40 in total

1.  Efficient and stereoselective synthesis of α(2→9) oligosialic acids: from monomers to dodecamers.

Authors:  Kuo-Ching Chu; Chien-Tai Ren; Chun-Ping Lu; Che-Hsiung Hsu; Tsung-Hsien Sun; Jeng-Liang Han; Bikash Pal; Tsung-An Chao; Yung-Feng Lin; Shih-Hsiung Wu; Chi-Huey Wong; Chung-Yi Wu
Journal:  Angew Chem Int Ed Engl       Date:  2011-08-29       Impact factor: 15.336

2.  Stereoselective synthesis of alpha-keto-deoxy-D-glycero-D-galacto-nonulosonic acid glycosides by means of the 4,5-O-carbonate protecting group.

Authors:  David Crich; Chandrasekhar Navuluri
Journal:  Angew Chem Int Ed Engl       Date:  2010-04-12       Impact factor: 15.336

3.  Nature of dynamic processes associated with the S(N)1 reaction mechanism.

Authors:  Kevin S Peters
Journal:  Chem Rev       Date:  2007-02-24       Impact factor: 60.622

Review 4.  Uronic acids in oligosaccharide and glycoconjugate synthesis.

Authors:  Jeroen D C Codée; Alphert E Christina; Marthe T C Walvoort; Herman S Overkleeft; Gijsbert A van der Marel
Journal:  Top Curr Chem       Date:  2011

Review 5.  Effect of electron-withdrawing protecting groups at remote positions of donors on glycosylation stereochemistry.

Authors:  Kwan Soo Kim; Dae-Hwan Suk
Journal:  Top Curr Chem       Date:  2011

6.  Stereoselective synthesis of oligo-alpha-(2,8)-sialic acids.

Authors:  Hiroshi Tanaka; Yuji Nishiura; Takashi Takahashi
Journal:  J Am Chem Soc       Date:  2006-06-07       Impact factor: 15.419

7.  N-benzyl-2,3-oxazolidinone as a glycosyl donor for selective alpha-glycosylation and one-pot oligosaccharide synthesis involving 1,2-cis-glycosylation.

Authors:  Shino Manabe; Kazuyuki Ishii; Yukishige Ito
Journal:  J Am Chem Soc       Date:  2006-08-23       Impact factor: 15.419

8.  Stereoselective, electrophilic α-C-sialidation.

Authors:  Amandine Noel; Bernard Delpech; David Crich
Journal:  Org Lett       Date:  2012-02-15       Impact factor: 6.005

9.  Dehydrative sialylation with C2-hemiketal sialyl donors.

Authors:  Jannine M Haberman; David Y Gin
Journal:  Org Lett       Date:  2003-07-10       Impact factor: 6.005

10.  Stereoselective iterative one-pot synthesis of N-glycolylneuraminic acid-containing oligosaccharides.

Authors:  David Crich; Baolin Wu
Journal:  Org Lett       Date:  2008-08-21       Impact factor: 6.005
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  17 in total

1.  Synthesis of an Aminooxy Derivative of the GM3 Antigen and Its Application in Oxime Ligation.

Authors:  Kristopher A Kleski; Mengchao Shi; Matthew Lohman; Gabrielle T Hymel; Vinod K Gattoji; Peter R Andreana
Journal:  J Org Chem       Date:  2020-05-01       Impact factor: 4.354

Review 2.  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

3.  Synthesis and intramolecular glycosylation of sialyl mono-esters of o-xylylene glycol. The importance of donor configuration and nitrogen protecting groups on cyclization yield and selectivity; isolation and characterization of a N-sialyl acetamide indicative of participation by acetonitrile.

Authors:  Harsha Amarasekara; David Crich
Journal:  Carbohydr Res       Date:  2016-10-08       Impact factor: 2.104

4.  Mechanism of Glycosylation of Anomeric Sulfonium Ions.

Authors:  Tao Fang; Yi Gu; Wei Huang; Geert-Jan Boons
Journal:  J Am Chem Soc       Date:  2016-02-29       Impact factor: 15.419

5.  Influence of Linkage Stereochemistry and Protecting Groups on Glycosidic Bond Stability of Sodium Cationized Glycosyl Phosphates.

Authors:  Y Zhu; Zhihua Yang; M T Rodgers
Journal:  J Am Soc Mass Spectrom       Date:  2017-09-18       Impact factor: 3.109

6.  The isothiocyanato moiety: an ideal protecting group for the stereoselective synthesis of sialic acid glycosides and subsequent diversification.

Authors:  Appi Reddy Mandhapati; Salla Rajender; Jonathan Shaw; David Crich
Journal:  Angew Chem Int Ed Engl       Date:  2014-11-28       Impact factor: 15.336

7.  Influence of protecting groups on O- and C-glycosylation with neuraminyl and ulosonyl dibutylphosphates.

Authors:  Riku Ogasahara; Shuay Abdullayev; Vikram A Sarpe; Appi Reddy Mandhapati; David Crich
Journal:  Carbohydr Res       Date:  2020-07-28       Impact factor: 2.104

8.  Probing the influence of a 4,6-O-acetal on the reactivity of galactopyranosyl donors: verification of the disarming influence of the trans-gauche conformation of C5-C6 bonds.

Authors:  Myriame Moumé-Pymbock; Takayuki Furukawa; Sujit Mondal; David Crich
Journal:  J Am Chem Soc       Date:  2013-09-11       Impact factor: 15.419

Review 9.  A propos of glycosyl cations and the mechanism of chemical glycosylation; the current state of the art.

Authors:  Luis Bohé; David Crich
Journal:  Carbohydr Res       Date:  2014-07-01       Impact factor: 2.104

10.  Exploration of the Oxazolidinthione Protecting System for the Synthesis of Sialic Acid Glycosides.

Authors:  Salla Rajender; David Crich
Journal:  J Carbohydr Chem       Date:  2013-09-02       Impact factor: 1.667
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