Synthesis of Methylene Tetrahydrofurane-Fused Carbohydrates

Maryam Ahmadian-Moghaddam; Niels R.M. Reintjens; Martin D. Witte; Adriaan J. Minnaard

doi:10.1002/ejoc.202300281

Synthesis of Methylene Tetrahydrofurane-Fused Carbohydrates

Maryam Ahmadian-Moghaddam, Niels R.M. Reintjens, Martin D. Witte^*, Adriaan J. Minnaard^*

^*Corresponding author for this work

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

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Abstract

A reliable method is disclosed to introduce a fused methylene tetrahydrofuran ring into carbohydrates. The resulting bicyclic saccharides can be used as scaffolds in medicinal chemistry and drug design. In addition, the enol ether functionality serves as a handle that enables modification in biological systems via photoclick chemistry. The approach is based on the regioselective oxidation of the C-3 hydroxy group in gluco-configured pyranosides, followed by stereoselective indium-mediated allylation. The ring formation is induced by an iodocyclization reaction with a neighboring hydroxy group. Subsequent dehydrohalogenation affords the desired methylene-tetrahydrofuran-containing carbohydrates.

Original language	English
Article number	e202300281
Number of pages	11
Journal	European Journal of Organic Chemistry
Volume	26
Issue number	20
DOIs	https://doi.org/10.1002/ejoc.202300281
Publication status	Published - 22-May-2023

Keywords

carbohydrates
enol ether
iodocyclization
photoclick
site selectivity

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10.1002/ejoc.202300281Licence: CC BY

Synthesis of Methylene Tetrahydrofurane‐Fused CarbohydratesFinal publisher's version, 3.7 MBLicence: CC BY

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@article{86f3bc39ccd24d749202612a4fe467d0,

title = "Synthesis of Methylene Tetrahydrofurane-Fused Carbohydrates",

abstract = "A reliable method is disclosed to introduce a fused methylene tetrahydrofuran ring into carbohydrates. The resulting bicyclic saccharides can be used as scaffolds in medicinal chemistry and drug design. In addition, the enol ether functionality serves as a handle that enables modification in biological systems via photoclick chemistry. The approach is based on the regioselective oxidation of the C-3 hydroxy group in gluco-configured pyranosides, followed by stereoselective indium-mediated allylation. The ring formation is induced by an iodocyclization reaction with a neighboring hydroxy group. Subsequent dehydrohalogenation affords the desired methylene-tetrahydrofuran-containing carbohydrates.",

keywords = "carbohydrates, enol ether, iodocyclization, photoclick, site selectivity",

author = "Maryam Ahmadian-Moghaddam and Reintjens, {Niels R.M.} and Witte, {Martin D.} and Minnaard, {Adriaan J.}",

note = "Funding Information: We acknowledge Prof. Dr. E. Otten, and J. van der Velde, University of Groningen, for X‐ray crystallography studies. We thank Y. Fu, University of Groningen, for assistance with the photoclick reaction, G. Boerema, University of Groningen, for the melting point analysis, and the University of Groningen for funding. Publisher Copyright: {\textcopyright} 2023 The Authors. European Journal of Organic Chemistry published by Wiley-VCH GmbH.",

year = "2023",

month = may,

day = "22",

doi = "10.1002/ejoc.202300281",

language = "English",

volume = "26",

journal = "European Journal of Organic Chemistry",

issn = "1434-193X",

publisher = "WILEY-V C H VERLAG GMBH",

number = "20",

}

TY - JOUR

T1 - Synthesis of Methylene Tetrahydrofurane-Fused Carbohydrates

AU - Ahmadian-Moghaddam, Maryam

AU - Reintjens, Niels R.M.

AU - Witte, Martin D.

AU - Minnaard, Adriaan J.

N1 - Funding Information: We acknowledge Prof. Dr. E. Otten, and J. van der Velde, University of Groningen, for X‐ray crystallography studies. We thank Y. Fu, University of Groningen, for assistance with the photoclick reaction, G. Boerema, University of Groningen, for the melting point analysis, and the University of Groningen for funding. Publisher Copyright: © 2023 The Authors. European Journal of Organic Chemistry published by Wiley-VCH GmbH.

PY - 2023/5/22

Y1 - 2023/5/22

N2 - A reliable method is disclosed to introduce a fused methylene tetrahydrofuran ring into carbohydrates. The resulting bicyclic saccharides can be used as scaffolds in medicinal chemistry and drug design. In addition, the enol ether functionality serves as a handle that enables modification in biological systems via photoclick chemistry. The approach is based on the regioselective oxidation of the C-3 hydroxy group in gluco-configured pyranosides, followed by stereoselective indium-mediated allylation. The ring formation is induced by an iodocyclization reaction with a neighboring hydroxy group. Subsequent dehydrohalogenation affords the desired methylene-tetrahydrofuran-containing carbohydrates.

AB - A reliable method is disclosed to introduce a fused methylene tetrahydrofuran ring into carbohydrates. The resulting bicyclic saccharides can be used as scaffolds in medicinal chemistry and drug design. In addition, the enol ether functionality serves as a handle that enables modification in biological systems via photoclick chemistry. The approach is based on the regioselective oxidation of the C-3 hydroxy group in gluco-configured pyranosides, followed by stereoselective indium-mediated allylation. The ring formation is induced by an iodocyclization reaction with a neighboring hydroxy group. Subsequent dehydrohalogenation affords the desired methylene-tetrahydrofuran-containing carbohydrates.

KW - carbohydrates

KW - enol ether

KW - iodocyclization

KW - photoclick

KW - site selectivity

UR - http://www.scopus.com/inward/record.url?scp=85159178392&partnerID=8YFLogxK

U2 - 10.1002/ejoc.202300281

DO - 10.1002/ejoc.202300281

M3 - Article

AN - SCOPUS:85159178392

SN - 1434-193X

VL - 26

JO - European Journal of Organic Chemistry

JF - European Journal of Organic Chemistry

IS - 20

M1 - e202300281

ER -

Synthesis of Methylene Tetrahydrofurane-Fused Carbohydrates

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Keywords

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CCDC 2158736: Experimental Crystal Structure Determination

CCDC 2158459: Experimental Crystal Structure Determination

CCDC 2158464: Experimental Crystal Structure Determination

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Synthesis of Methylene Tetrahydrofurane-Fused Carbohydrates

Abstract

Keywords

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CCDC 2158736: Experimental Crystal Structure Determination

CCDC 2158459: Experimental Crystal Structure Determination

CCDC 2158464: Experimental Crystal Structure Determination

Cite this