Indium-mediated allylation of disaccharides

Christian Denner; Manuel Gintner; Hanspeter Kählig; Tanja M Wrodnigg; Walther Schmid

doi:10.1016/j.carres.2020.108170

Indium-mediated allylation of disaccharides

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

^*Corresponding author for this work

Institute of Chemistry and Technology of Biobased Systems (6430)

Research output: Contribution to journal › Article › peer-review

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.

Original language	English
Article number	108170
Journal	Carbohydrate Research
Volume	498
Early online date	8 Oct 2020
DOIs	https://doi.org/10.1016/j.carres.2020.108170
Publication status	Published - Dec 2020

Keywords

C–C bond formation
Disaccharide
Indium-mediated allylation
Ozonolysis

ASJC Scopus subject areas

Analytical Chemistry
Biochemistry
Organic Chemistry

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10.1016/j.carres.2020.108170

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title = "Indium-mediated allylation of disaccharides",

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.",

keywords = "C–C bond formation, Disaccharide, Indium-mediated allylation, Ozonolysis",

author = "Christian Denner and Manuel Gintner and Hanspeter K{\"a}hlig and Wrodnigg, {Tanja M} and Walther Schmid",

year = "2020",

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doi = "10.1016/j.carres.2020.108170",

language = "English",

volume = "498",

journal = "Carbohydrate Research",

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T1 - Indium-mediated allylation of disaccharides

AU - Denner, Christian

AU - Gintner, Manuel

AU - Kählig, Hanspeter

AU - Wrodnigg, Tanja M

AU - Schmid, Walther

PY - 2020/12

Y1 - 2020/12

N2 - 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.

AB - 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.

KW - C–C bond formation

KW - Disaccharide

KW - Indium-mediated allylation

KW - Ozonolysis

UR - http://www.scopus.com/inward/record.url?scp=85092469873&partnerID=8YFLogxK

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DO - 10.1016/j.carres.2020.108170

M3 - Article

C2 - 33068775

SN - 0008-6215

VL - 498

JO - Carbohydrate Research

JF - Carbohydrate Research

M1 - 108170

ER -

Indium-mediated allylation of disaccharides

Abstract

Keywords

ASJC Scopus subject areas

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