Heteroglycoclusters through Unprecedented Orthogonal Chemistry Based on N-Alkylation of N-Acylhydrazone

Marwa Frey; David Mathiron; Serge Pilard; David Lesur; Rym Abidi; Thouraya Barhoumi-Slimi; Peter Cragg; Mohammed  Benazza

doi:10.1002/ejoc.202101537

Heteroglycoclusters through Unprecedented Orthogonal Chemistry Based on N-Alkylation of N-Acylhydrazone

Marwa Frey
, David Mathiron
, Serge Pilard
, David Lesur
, Rym Abidi
, Thouraya Barhoumi-Slimi
, Peter Cragg
, Mohammed Benazza

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

Abstract

Orthogonal chemistry is a valuable tool in the preparation of complex molecules as heteroglycoclusters. Unfortunately, selective heteroconjugation of multifunctional starting materials remains a usually challenging problem to overcome. Herein, we report the first report on harnessing N-alkylation of N-acylhydrazone as a key step in the orthogonal synthesis. Sequentially associated with the azido-alkyne click chemistry, it stands out as a new and straightforward synthetic method of glycoconjugate small molecules, heterodisaccharides, and heteroglycoclusters based on cone p-tBu-calix[4]arene and 1,3-alt p-tBu-thiacalix[4]arene with potential drug-like properties.

Original language	English
Article number	e202101537
Number of pages	12
Journal	European Journal of Organic Chemistry
Volume	2022
Issue number	33
DOIs	https://doi.org/10.1002/ejoc.202101537
Publication status	Published - 9 Mar 2022

Bibliographical note

Funding Information:
Support from the LG2 A‐UMR7378‐CNRS research group is gratefully acknowledged. M. Fray was financially supported by a scholarship from the Tunisian government.

Publisher Copyright:
© 2022 Wiley-VCH GmbH.

Keywords

Cone calix/1,3-alt thiacalixarene
Heteroglycoclusters
N-acylhydrazone
N-alkyl-N-acylhydrazone
Orthogonal chemistry

Access to Document

10.1002/ejoc.202101537

Cite this

@article{144d5c7af47840749856339d184f2eeb,

title = "Heteroglycoclusters through Unprecedented Orthogonal Chemistry Based on N-Alkylation of N-Acylhydrazone",

abstract = "Orthogonal chemistry is a valuable tool in the preparation of complex molecules as heteroglycoclusters. Unfortunately, selective heteroconjugation of multifunctional starting materials remains a usually challenging problem to overcome. Herein, we report the first report on harnessing N-alkylation of N-acylhydrazone as a key step in the orthogonal synthesis. Sequentially associated with the azido-alkyne click chemistry, it stands out as a new and straightforward synthetic method of glycoconjugate small molecules, heterodisaccharides, and heteroglycoclusters based on cone p-tBu-calix[4]arene and 1,3-alt p-tBu-thiacalix[4]arene with potential drug-like properties.",

keywords = "Cone calix/1,3-alt thiacalixarene, Heteroglycoclusters, N-acylhydrazone, N-alkyl-N-acylhydrazone, Orthogonal chemistry",

author = "Marwa Frey and David Mathiron and Serge Pilard and David Lesur and Rym Abidi and Thouraya Barhoumi-Slimi and Peter Cragg and Mohammed Benazza",

note = "Funding Information: Support from the LG2 A‐UMR7378‐CNRS research group is gratefully acknowledged. M. Fray was financially supported by a scholarship from the Tunisian government. Publisher Copyright: {\textcopyright} 2022 Wiley-VCH GmbH.",

year = "2022",

month = mar,

day = "9",

doi = "10.1002/ejoc.202101537",

language = "English",

volume = "2022",

journal = "European Journal of Organic Chemistry",

issn = "1434-193X",

number = "33",

}

TY - JOUR

T1 - Heteroglycoclusters through Unprecedented Orthogonal Chemistry Based on N-Alkylation of N-Acylhydrazone

AU - Frey, Marwa

AU - Mathiron, David

AU - Pilard, Serge

AU - Lesur, David

AU - Abidi, Rym

AU - Barhoumi-Slimi, Thouraya

AU - Cragg, Peter

AU - Benazza, Mohammed

N1 - Funding Information: Support from the LG2 A‐UMR7378‐CNRS research group is gratefully acknowledged. M. Fray was financially supported by a scholarship from the Tunisian government. Publisher Copyright: © 2022 Wiley-VCH GmbH.

PY - 2022/3/9

Y1 - 2022/3/9

N2 - Orthogonal chemistry is a valuable tool in the preparation of complex molecules as heteroglycoclusters. Unfortunately, selective heteroconjugation of multifunctional starting materials remains a usually challenging problem to overcome. Herein, we report the first report on harnessing N-alkylation of N-acylhydrazone as a key step in the orthogonal synthesis. Sequentially associated with the azido-alkyne click chemistry, it stands out as a new and straightforward synthetic method of glycoconjugate small molecules, heterodisaccharides, and heteroglycoclusters based on cone p-tBu-calix[4]arene and 1,3-alt p-tBu-thiacalix[4]arene with potential drug-like properties.

AB - Orthogonal chemistry is a valuable tool in the preparation of complex molecules as heteroglycoclusters. Unfortunately, selective heteroconjugation of multifunctional starting materials remains a usually challenging problem to overcome. Herein, we report the first report on harnessing N-alkylation of N-acylhydrazone as a key step in the orthogonal synthesis. Sequentially associated with the azido-alkyne click chemistry, it stands out as a new and straightforward synthetic method of glycoconjugate small molecules, heterodisaccharides, and heteroglycoclusters based on cone p-tBu-calix[4]arene and 1,3-alt p-tBu-thiacalix[4]arene with potential drug-like properties.

KW - Cone calix/1,3-alt thiacalixarene

KW - Heteroglycoclusters

KW - N-acylhydrazone

KW - N-alkyl-N-acylhydrazone

KW - Orthogonal chemistry

UR - https://www.scopus.com/pages/publications/85127589337

U2 - 10.1002/ejoc.202101537

DO - 10.1002/ejoc.202101537

M3 - Article

SN - 1434-193X

VL - 2022

JO - European Journal of Organic Chemistry

JF - European Journal of Organic Chemistry

IS - 33

M1 - e202101537

ER -

Heteroglycoclusters through Unprecedented Orthogonal Chemistry Based on N-Alkylation of N-Acylhydrazone

Abstract

Bibliographical note

Keywords

Access to Document

Other files and links

Fingerprint

Cite this