Indium-mediated allylation of disaccharides

Christian Denner*, Manuel Gintner, Hanspeter Kählig, Tanja M Wrodnigg, Walther Schmid

*Korrespondierende/r Autor/-in für diese Arbeit

Publikation: Beitrag in einer FachzeitschriftArtikelBegutachtung

Abstract

The indium-mediated allylation followed by ozonolysis has been applied for the elongation of different disaccharides such as cellobiose, lactose and maltose. This reaction sequence and per-O-acetylation produced the expected mixture of α/β-pyranoid as well as α/β-furanoid isomers. The main product in all cases adopted the β-pyranose form and could be isolated and fully characterized with the help of NMR-spin simulations. Thorough investigation of the side products throughout optimization of the conditions for the ozonolysis resulted in the discovery of a novel 12 membered bridged disaccharide.

Originalspracheenglisch
Aufsatznummer108170
FachzeitschriftCarbohydrate Research
Jahrgang498
Frühes Online-Datum8 Okt. 2020
DOIs
PublikationsstatusVeröffentlicht - Dez. 2020

ASJC Scopus subject areas

  • Analytische Chemie
  • Biochemie
  • Organische Chemie

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