Length Matters: One Additional Methylene Group in a Reactant is Able to Affect the Reactivity Pattern and Significantly Increase the Product Yield

Elena V. Stepanova, Nikita M. Podvalnyy, Polina I. Abronina, Leonid O. Kononov

Research output: Contribution to journalArticle

6 Citations (Scopus)

Abstract

The outcome of the nucleophilic opening of 3- O -benzoyl-β- d -arabinofuranose 1,2,5-orthobenzoate with 4-(ω-chloroalkoxy)phenols (SnCl 4, CH 2 Cl 2, -25 °C) unusually strongly depends on the length of the methylene chain of the nucleophile. The presence of one extra methylene group in the molecule of 4-(3-chloropropoxy)phenol [as compared to 4-(2-chloroetoxy)phenol] results in four-fold reduction in the reaction time and five-fold increase in the yield of a selectively protected monosaccharide glycoside with a hydroxy group at C-5, which is a valuable building block for the synthesis of oligoarabinofuranosides related to mycobacterial arabinans. Possible reasons and consequences of this finding are discussed.

Original languageEnglish
Article numberst-2018-b0212-l
Pages (from-to)2043-2045
Number of pages3
JournalSynlett
Volume29
Issue number15
DOIs
Publication statusPublished - 2018

Keywords

  • glycosylation
  • mycobacterial arabinans
  • oligosaccharides
  • orthoesters
  • phenols
  • reactivity pattern
  • solution structure
  • substituent effects

ASJC Scopus subject areas

  • Organic Chemistry

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