Literature DB >> 19053743

Efficient synthesis of an alpha(2,9) trisialic acid by one-pot glycosylation and polymer-assisted deprotection.

Hiroshi Tanaka1, Yusuke Tateno, Yuji Nishiura, Takashi Takahashi.   

Abstract

An efficient synthesis of alpha(2,9) trisialic acid has been achieved via one-pot glycosylation and polymer-assisted deprotection. The synthesis involves chemo- and regioselective alpha-sialylation of ethylthiosialoside with the S-benzoxazolyl (S-Box) sialyl donor. Use of a prelinker to link an activated ester and a vinyl ether via a carbon chain enables polymer-assisted deprotection of the protected trisialic acids.

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Year:  2008        PMID： 19053743     DOI： 10.1021/ol802207e

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


  8 in total

1.  Pre-activation Based Stereoselective Glycosylations.

Authors:  Bo Yang; Weizhun Yang; Sherif Ramadan; Xuefei Huang
Journal:  European J Org Chem       Date:  2017-12-28

2.  Synthesis and immunological study of α-2,9-oligosialic acid conjugates as anti-group C meningitis vaccines.

Authors:  Guochao Liao; Zhifang Zhou; Zhongwu Guo
Journal:  Chem Commun (Camb)       Date:  2015-06-14       Impact factor: 6.222

Review 3.  Recent progress in chemical and chemoenzymatic synthesis of carbohydrates.

Authors:  Saddam Muthana; Hongzhi Cao; Xi Chen
Journal:  Curr Opin Chem Biol       Date:  2009-10-14       Impact factor: 8.822

4.  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

Review 5.  Opportunities and challenges in synthetic oligosaccharide and glycoconjugate research.

Authors:  Thomas J Boltje; Therese Buskas; Geert-Jan Boons
Journal:  Nat Chem       Date:  2009-11       Impact factor: 24.427

6.  Probing the influence of protecting groups on the anomeric equilibrium in sialic acid glycosides with the persistent radical effect.

Authors:  Pavan K Kancharla; Takayuki Kato; David Crich
Journal:  J Am Chem Soc       Date:  2014-04-01       Impact factor: 15.419

7.  Synthetically defined glycoprotein vaccines: current status and future directions.

Authors:  Roberto Adamo; Alberto Nilo; Bastien Castagner; Omar Boutureira; Francesco Berti; Gonçalo J L Bernardes
Journal:  Chem Sci       Date:  2013-05-16       Impact factor: 9.825

Review 8.  Chemical O-Glycosylations: An Overview.

Authors:  Rituparna Das; Balaram Mukhopadhyay
Journal:  ChemistryOpen       Date:  2016-08-17       Impact factor: 2.911
  8 in total

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