Literature DB >> 32627548

Indolylthio Glycosides As Effective Building Blocks for Chemical Glycosylation.

Ganesh Shrestha1, Matteo Panza1, Yashapal Singh1, Nigam P Rath1, Alexei V Demchenko1.   

Abstract

The S-indolyl (SIn) anomeric moiety was investigated as a new leaving group that can be activated for chemical glycosylation under a variety of conditions including thiophilic and metal-assisted pathways. Understanding of the reaction pathways for the SIn moiety activation was achieved via the extended mechanistic study. Also reported is how the new SIn donors fit into selective activation strategies for oligosaccharide synthesis.

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Year:  2020        PMID： 32627548      PMCID： PMC8114089          DOI： 10.1021/acs.joc.0c00943

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


  25 in total

1.  Koenigs-Knorr Glycosylation Reaction Catalyzed by Trimethylsilyl Trifluoromethanesulfonate.

Authors:  Yashapal Singh; Alexei V Demchenko
Journal:  Chemistry       Date:  2018-12-20       Impact factor: 5.236

Review 2.  A comprehensive review of glycosylated bacterial natural products.

Authors:  Sherif I Elshahawi; Khaled A Shaaban; Madan K Kharel; Jon S Thorson
Journal:  Chem Soc Rev       Date:  2015-11-07       Impact factor: 54.564

3.  An Empirical Understanding of the Glycosylation Reaction.

Authors:  Sourav Chatterjee; Sooyeon Moon; Felix Hentschel; Kerry Gilmore; Peter H Seeberger
Journal:  J Am Chem Soc       Date:  2018-09-18       Impact factor: 15.419

4.  S-thiazolinyl (STaz) glycosides as versatile building blocks for convergent selective, chemoselective, and orthogonal oligosaccharide synthesis.

Authors:  Papapida Pornsuriyasak; Alexei V Demchenko
Journal:  Chemistry       Date:  2006-08-25       Impact factor: 5.236

5.  Concise syntheses of the cruciferous phytoalexins brassilexin, sinalexin, wasalexins, and analogues: expanding the scope of the vilsmeier formylation.

Authors:  M Soledade C Pedras; Mukund Jha
Journal:  J Org Chem       Date:  2005-03-04       Impact factor: 4.354

6.  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

7.  S-Benzoxazolyl (SBox) glycosides as novel, versatile glycosyl donors for stereoselective 1,2-cis glycosylation.

Authors:  Alexei V Demchenko; Nelli N Malysheva; Cristina De Meo
Journal:  Org Lett       Date:  2003-02-20       Impact factor: 6.005

8.  A Highly Efficient Glycosidation of Glycosyl Chlorides by Using Cooperative Silver(I) Oxide-Triflic Acid Catalysis.

Authors:  Scott A Geringer; Yashapal Singh; Daniel J Hoard; Alexei V Demchenko
Journal:  Chemistry       Date:  2020-06-02       Impact factor: 5.236

9.  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

10.  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
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