A New Platform Molecule from Gluconolactone? Access to Furanics, Rare Sugars, β-Ketoamides and Amino Furanones

Arminas Jurys; Christian Marcus Pedersen

doi:10.1002/chem.202403453

A New Platform Molecule from Gluconolactone? Access to Furanics, Rare Sugars, β-Ketoamides and Amino Furanones

Arminas Jurys
, Christian Marcus Pedersen^*

^*Corresponding author af dette arbejde

Kemisk Institut

Publikation: Bidrag til tidsskrift › Tidsskriftartikel › Forskning › peer review

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Abstract

Gluconolactone serves as a readily available and inexpensive starting material for synthesizing the potential platform chemical (Z)-3-deoxy-1,2 : 5,6-di-O-isopropylidene-D-erythro-hex-3-enolactone in two steps. In this work, the selective elimination of triacetone gluconolactone was optimized. The resulting product is a versatile molecule, capable of being transformed into various compound classes in one or a few steps, i. e. potentially a new biomass-based platform chemical. This study demonstrates how it can be transformed into furanics, rare sugars, β-ketoamides, and amino furanones.

Originalsprog	Engelsk
Artikelnummer	e202403453
Tidsskrift	Chemistry - A European Journal
Vol/bind	31
Udgave nummer	1
Antal sider	7
ISSN	0947-6539
DOI	https://doi.org/10.1002/chem.202403453
Status	Udgivet - 2025

Bibliografisk note

Publisher Copyright:
© 2024 The Author(s). Chemistry - A European Journal published by Wiley-VCH GmbH.

Finansiering

Independent Research Fund Denmark (DFF) Technology and Production Sciences is acknowledged for financial support (grant number 2035\u201300009B). The authors are grateful for use of the Novo Nordisk Foundation NMR facility at the Department of Chemistry at Copenhagen University (NNF21OC0067315).

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10.1002/chem.202403453

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Citationsformater

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title = "A New Platform Molecule from Gluconolactone? Access to Furanics, Rare Sugars, β-Ketoamides and Amino Furanones",

abstract = "Gluconolactone serves as a readily available and inexpensive starting material for synthesizing the potential platform chemical (Z)-3-deoxy-1,2 : 5,6-di-O-isopropylidene-D-erythro-hex-3-enolactone in two steps. In this work, the selective elimination of triacetone gluconolactone was optimized. The resulting product is a versatile molecule, capable of being transformed into various compound classes in one or a few steps, i. e. potentially a new biomass-based platform chemical. This study demonstrates how it can be transformed into furanics, rare sugars, β-ketoamides, and amino furanones.",

keywords = "Biomass based chemicals, Carbohydrates, Catalysis, Chiral pool, Furanics",

author = "Arminas Jurys and Pedersen, \{Christian Marcus\}",

note = "Funding Information: Independent Research Fund Denmark (DFF) Technology and Production Sciences is acknowledged for financial support (grant number 2035\textbackslash{}u201300009B). The authors are grateful for use of the Novo Nordisk Foundation NMR facility at the Department of Chemistry at Copenhagen University (NNF21OC0067315). Publisher Copyright: {\textcopyright} 2024 The Author(s). Chemistry - A European Journal published by Wiley-VCH GmbH.",

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AU - Jurys, Arminas

AU - Pedersen, Christian Marcus

N1 - Funding Information: Independent Research Fund Denmark (DFF) Technology and Production Sciences is acknowledged for financial support (grant number 2035\u201300009B). The authors are grateful for use of the Novo Nordisk Foundation NMR facility at the Department of Chemistry at Copenhagen University (NNF21OC0067315). Publisher Copyright: © 2024 The Author(s). Chemistry - A European Journal published by Wiley-VCH GmbH.

PY - 2025

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N2 - Gluconolactone serves as a readily available and inexpensive starting material for synthesizing the potential platform chemical (Z)-3-deoxy-1,2 : 5,6-di-O-isopropylidene-D-erythro-hex-3-enolactone in two steps. In this work, the selective elimination of triacetone gluconolactone was optimized. The resulting product is a versatile molecule, capable of being transformed into various compound classes in one or a few steps, i. e. potentially a new biomass-based platform chemical. This study demonstrates how it can be transformed into furanics, rare sugars, β-ketoamides, and amino furanones.

AB - Gluconolactone serves as a readily available and inexpensive starting material for synthesizing the potential platform chemical (Z)-3-deoxy-1,2 : 5,6-di-O-isopropylidene-D-erythro-hex-3-enolactone in two steps. In this work, the selective elimination of triacetone gluconolactone was optimized. The resulting product is a versatile molecule, capable of being transformed into various compound classes in one or a few steps, i. e. potentially a new biomass-based platform chemical. This study demonstrates how it can be transformed into furanics, rare sugars, β-ketoamides, and amino furanones.

KW - Biomass based chemicals

KW - Carbohydrates

KW - Catalysis

KW - Chiral pool

KW - Furanics

U2 - 10.1002/chem.202403453

DO - 10.1002/chem.202403453

M3 - Journal article

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AN - SCOPUS:85209794087

SN - 0947-6539

VL - 31

JO - Chemistry - A European Journal

JF - Chemistry - A European Journal

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