Literature DB >> 15548064

A novel strategy for oligosaccharide synthesis via temporarily deactivated S-thiazolyl glycosides as glycosyl acceptors.

Papapida Pornsuriyasak1, Umesh B Gangadharmath, Nigam P Rath, Alexei V Demchenko.   

Abstract

A new glycosylation strategy that allows chemoselective activation of the S-thiazolyl (STaz) moiety of a glycosyl donor over the temporarily deactivated glycosyl acceptor, bearing the same anomeric group, has been developed. This deactivation is achieved by engaging of the STaz moiety of the glycosyl acceptor into a stable palladium(II) complex. Therefore, obtained disaccharides are then released from the complex by simple ligand exchange. [reaction: see text]

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Year:  2004        PMID： 15548064     DOI： 10.1021/ol048043y

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


  13 in total

1.  S-benzoxazolyl as a stable protecting moiety and a potent anomeric leaving group in oligosaccharide synthesis.

Authors:  Medha N Kamat; Cristina De Meo; Alexei V Demchenko
Journal:  J Org Chem       Date:  2007-08-04       Impact factor: 4.354

2.  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

3.  Recent advances in heterolytic nucleofugal leaving groups.

Authors:  Salvatore D Lepore; Deboprosad Mondal
Journal:  Tetrahedron       Date:  2007-06-11       Impact factor: 2.457

4.  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

5.  Iterative one-pot syntheses of chitotetroses.

Authors:  Lijun Huang; Zhen Wang; Xiaoning Li; Xin-shan Ye; Xuefei Huang
Journal:  Carbohydr Res       Date:  2006-01-26       Impact factor: 2.104

6.  S-Benzimidazolyl glycosides as a platform for oligosaccharide synthesis by an active-latent strategy.

Authors:  Scott J Hasty; Matthew A Kleine; Alexei V Demchenko
Journal:  Angew Chem Int Ed Engl       Date:  2011-03-23       Impact factor: 15.336

7.  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

8.  4-(pyridin-2-yl)thiazol-2-yl thioglycosides as bidentate ligands for oligosaccharide synthesis via temporary deactivation.

Authors:  Papapida Pornsuriyasak; Nigam P Rath; Alexei V Demchenko
Journal:  Chem Commun (Camb)       Date:  2008-10-01       Impact factor: 6.222

9.  Silver(I) tetrafluoroborate as a potent promoter for chemical glycosylation.

Authors:  Sophon Kaeothip; Papapida Pornsuriyasak; Alexei V Demchenko
Journal:  Tetrahedron Lett       Date:  2008-02-25       Impact factor: 2.415

10.  Synthetic and Mechanistic Studies of a Versatile Heteroaryl Thioether Directing Group for Pd(II) Catalysis.

Authors:  Jason S Chen; Andrew M Romine; Kin S Yang; Malkanthi K Karunananda; Keary M Engle
Journal:  ACS Catal       Date:  2019-07-02       Impact factor: 13.084
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