Indium-mediated allylation of disaccharides.

Alkenes / chemistry Catalysis Disaccharides / chemistry Indium / chemistry Isomerism Ozone / chemistry
C–C bond formation Disaccharide Indium-mediated allylation Ozonolysis

Journal

Carbohydrate research
ISSN: 1873-426X
Titre abrégé: Carbohydr Res
Pays: Netherlands
ID NLM: 0043535

Informations de publication

Date de publication:
Dec 2020
Historique:
received: 07 07 2020
revised: 24 09 2020
accepted: 30 09 2020
pubmed: 18 10 2020
medline: 24 8 2021
entrez: 17 10 2020
Statut: ppublish

Résumé

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.

Identifiants

DOI: 10.1016/j.carres.2020.108170 PMID: 33068775
pubmed: 33068775
pii: S0008-6215(20)30541-3
doi: 10.1016/j.carres.2020.108170
pii:
doi:

Substances chimiques

Alkenes 0
Disaccharides 0
Indium 045A6V3VFX
Ozone 66H7ZZK23N

Types de publication

Journal Article

Langues

eng

Sous-ensembles de citation

IM

Pagination

108170

Informations de copyright

Copyright © 2020 The Author(s). Published by Elsevier Ltd.. All rights reserved.

Auteurs

Christian Denner (C)

Institute of Organic Chemistry, University of Vienna, Währinger Straße 38, A-1090, Vienna, Austria. Electronic address: christian.denner@univie.ac.at.

Manuel Gintner (M)

Institute of Organic Chemistry, University of Vienna, Währinger Straße 38, A-1090, Vienna, Austria.

Hanspeter Kählig (H)

Institute of Organic Chemistry, University of Vienna, Währinger Straße 38, A-1090, Vienna, Austria.

Tanja M Wrodnigg (TM)

Glycogroup, Institute of Chemistry and Technology for Biobased Systems, Graz University of Technology, Stremayrgasse 9, A-8010, Graz, Austria.

Walther Schmid (W)

Institute of Organic Chemistry, University of Vienna, Währinger Straße 38, A-1090, Vienna, Austria.

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Classifications MeSH

questionsmedicales.fr › Composés chimiques organiques › Hydrocarbures › Hydrocarbures acycliques › Alcènes › Indium-mediated allylation of disaccharides.
questionsmedicales.fr › Phénomènes chimiques › Catalyse › Indium-mediated allylation of disaccharides.
questionsmedicales.fr › Glucides › Sucres › Diholoside › Indium-mediated allylation of disaccharides.
questionsmedicales.fr › Produits chimiques inorganiques › Métaux › Métaux lourds › Indium › Indium-mediated allylation of disaccharides.
questionsmedicales.fr › Phénomènes chimiques › Phénomènes de chimie organique › Isomérie › Indium-mediated allylation of disaccharides.
questionsmedicales.fr › Produits chimiques inorganiques › Gaz › Oxygène › Ozone › Indium-mediated allylation of disaccharides.