Literature DB >> 26634960

Aryl(trifluoroethyl)iodonium Triflimide and Nitrile Solvent Systems: A Combination for the Stereoselective Synthesis of Armed 1,2-trans-β-Glycosides at Noncryogenic Temperatures.

An-Hsiang Adam Chu1, Andrei Minciunescu1, Clay S Bennett1.   

Abstract

Armed thioglycosides can be activated with aryl(trifluoroethyl)iodonium triflimide in 2:1 CH2Cl2/pivalonitrile or a solvent combination of CH2Cl2, acetonitrile, isobutyronitrile, and pivalonitrile (6:1:1:1) at 0 °C for glycosylation reactions that proceed in good yield and moderate to excellent selectivity (up to 25:1 β/α). Comparison to other common glycosylation promoters reveals that both the mixed solvent and the iodonium salt promoter are required for stereoselectivity.

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Year:  2015        PMID： 26634960     DOI： 10.1021/acs.orglett.5b03282

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


  4 in total

Review 1.  Recent Advances in Stereoselective Chemical O-Glycosylation Reactions.

Authors:  Mana Mohan Mukherjee; Rina Ghosh; John A Hanover
Journal:  Front Mol Biosci       Date:  2022-06-14

2.  Challenges in the Conversion of Manual Processes to Machine-Assisted Syntheses: Activation of Thioglycoside Donors with Aryl(trifluoroethyl)iodonium Triflimide.

Authors:  Regis C Saliba; Zachary J Wooke; Gabriel A Nieves; An-Hsiang Adam Chu; Clay S Bennett; Nicola L B Pohl
Journal:  Org Lett       Date:  2018-01-16       Impact factor: 6.005

Review 3.  Glycosylation reactions mediated by hypervalent iodine: application to the synthesis of nucleosides and carbohydrates.

Authors:  Yuichi Yoshimura; Hideaki Wakamatsu; Yoshihiro Natori; Yukako Saito; Noriaki Minakawa
Journal:  Beilstein J Org Chem       Date:  2018-06-28       Impact factor: 2.883

4.  Efficient O-Functionalization of Carbohydrates with Electrophilic Reagents.

Authors:  Gergely L Tolnai; Ulf J Nilsson; Berit Olofsson
Journal:  Angew Chem Int Ed Engl       Date:  2016-08-16       Impact factor: 15.336
  4 in total

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