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Literature DB >> 17676918

Versatile synthesis and mechanism of activation of S-benzoxazolyl glycosides.

Medha N Kamat¹, Nigam P Rath, Alexei V Demchenko.

Abstract

As a part of a program for developing new efficient procedures for stereoselective glycosylation, a range of S-benzoxazolyl (SBox) glycosides have been synthesized. The mechanistic aspects of the SBox moiety activation for glycosylation via a variety of conceptually different pathways in the presence of thiophilic, electrophilic, or metal-based promoters have been investigated.

Entities: Chemical

Mesh：

Substances：

Year: 2007 PMID： 17676918 PMCID： PMC2535574 DOI： 10.1021/jo0711844

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

19 in total

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2. 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

Review 3. Chemical glycobiology.

Authors: C R Bertozzi; L L Kiessling
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4. Benzeneselenenyl triflate as an activator of thioglycosides for glycosylation reactions.

Authors: Y Ito; T Ogawa; M Numata; M Sugimoto
Journal: Carbohydr Res Date: 1990-07-15 Impact factor: 2.104

5. General one-step synthesis of free hexofuranosyl 1-phosphates using unprotected 1-thioimidoyl hexofuranosides.

Authors: Ronan Euzen; Vincent Ferrières; Daniel Plusquellec
Journal: J Org Chem Date: 2005-02-04 Impact factor: 4.354

6. Synthesis of N-unsubstituted, mono- and disubstituted carbohydrate-1-O-carbamates and their behaviour in glycoside syntheses.

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7. Enantioselective O- and N-nitroso aldol synthesis of tin enolates. Isolation of three BINAP-silver complexes and their role in regio- and enantioselectivity.

Authors: Norie Momiyama; Hisashi Yamamoto
Journal: J Am Chem Soc Date: 2004-05-05 Impact factor: 15.419

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

Authors: Papapida Pornsuriyasak; Umesh B Gangadharmath; Nigam P Rath; Alexei V Demchenko
Journal: Org Lett Date: 2004-11-25 Impact factor: 6.005

9. Glycosyl disulfides: novel glycosylating reagents with flexible aglycon alteration.

Authors: Elizabeth J Grayson; Sarah J Ward; Alison L Hall; Phillip M Rendle; David P Gamblin; Andrei S Batsanov; Benjamin G Davis
Journal: J Org Chem Date: 2005-11-25 Impact factor: 4.354

Review 10. Biological roles of oligosaccharides: all of the theories are correct.

Authors: A Varki
Journal: Glycobiology Date: 1993-04 Impact factor: 4.313

19 in total

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

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Journal: Org Lett Date: 2008-05-01 Impact factor: 6.005

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3. On orthogonal and selective activation of glycosyl thioimidates and thioglycosides: application to oligosaccharide assembly.

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Journal: J Org Chem Date: 2011-08-17 Impact factor: 4.354

4. Glycosyl alkoxythioimidates as complementary building blocks for chemical glycosylation.

Authors: Sneha C Ranade; Sophon Kaeothip; Alexei V Demchenko
Journal: Org Lett Date: 2010-11-18 Impact factor: 6.005

5. 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

6. HPLC-Assisted Automated Oligosaccharide Synthesis: Implementation of the Autosampler as a Mode of the Reagent Delivery.

Authors: Salvatore G Pistorio; Swati S Nigudkar; Keith J Stine; Alexei V Demchenko
Journal: J Org Chem Date: 2016-09-14 Impact factor: 4.354