Solvent Effect on Glycosylation

Kwok-Kong Mong*, Toshiki Nokami, Nhut Thi Thanh Tran, Pham Be Nhi

*Corresponding author for this work

Research output: Chapter in Book/Report/Conference proceedingChapter

5 Scopus citations

Abstract

Until now, glycosylation chemistry has still been dominated by the concept of Koenigs-Knorr glycosylation. The glycosyl oxocarbenium ion is accompanied with a counterion as an ion pair, which may exist as a close-contact ion pair (CCIP), a solvent separated ion pair (SSIP), and/or a covalent glycoside adduct. This chapter discusses the effect of solvent on glycosylation with respect to the physical properties of the solvent. A binary or quaternary solvent system contains two or more solvent components and is common in glycosylation. Based on the polarity and electron-pair-donating capacity, the chapter classifies the solvents used in glycosylation to weakly polar and noncoordinating solvents such as benzene and toluene; moderately polar and noncoordinating solvents such as CH2Cl2, CH3NO2, and C2H4Cl2; highly polar and coordinating solvents such as CH3CN and EtCN; and weakly polar and coordinating solvents such as diethyl ether (Et2O) and dioxane. The effects of these solvents in glycosylation are also described.

Original languageEnglish
Title of host publicationSelective Glycosylation
Subtitle of host publicationSynthetic Methods and Catalysts
PublisherWiley-VCH Verlag
Pages59-77
Number of pages19
ISBN (Electronic)9783527696239
ISBN (Print)9783527339877
DOIs
StatePublished - 9 Mar 2017

Keywords

  • Close-contact ion pair
  • Electrochemical glycosylation
  • Electron-pair-donating capacity
  • Glycosyl oxocarbenium ion
  • Ionic liquid solvents
  • Koenigs-Knorr glycosylation
  • Polar solvents
  • Solvent effect
  • Solvent separated ion pair

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  • Cite this

    Mong, K-K., Nokami, T., Tran, N. T. T., & Nhi, P. B. (2017). Solvent Effect on Glycosylation. In Selective Glycosylation: Synthetic Methods and Catalysts (pp. 59-77). Wiley-VCH Verlag. https://doi.org/10.1002/9783527696239.ch3