Glycoconjugates via Phosphorus Ylides

Ehsan Ghonchepour; Constantinos G. Neochoritis; Katarzyna Kurpiewska; Justyna Kalinowska-Tluscik; Mohammad R. Islami; Alexander Domling

doi:10.1002/ejoc.201900434

Glycoconjugates via Phosphorus Ylides

Ehsan Ghonchepour, Constantinos G. Neochoritis, Katarzyna Kurpiewska, Justyna Kalinowska-Tluscik, Mohammad R. Islami, Alexander Domling^*

^*Corresponding author for this work

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Abstract

A facile, high yielding access to rare chimeric compounds combining phosphorus ylides with complex glycosyl formamides is described. We determined X-ray structures gaining structural insight into this compounds class. In addition, data mining of similar compounds deposited within the Cambridge Structural Database was performed. These derivatives could be used either as synthetic intermediates via the ylide functionalization and glyco chemical biology synthons or improving the pharmacokinetic properties of a potential bioactive molecule, exploiting the glycosyl moiety.

Original language	English
Pages (from-to)	3632-3635
Number of pages	4
Journal	European Journal of Organic Chemistry
Volume	2019
Issue number	22
DOIs	https://doi.org/10.1002/ejoc.201900434
Publication status	Published - 16-Jun-2019

Keywords

Phosphorus Ylides
Glycoconjugates
Glycosyl Formamides
Multi-Component Reactions
Chemical Biology
ONE-POT SYNTHESIS
ACETYLENIC ESTERS
DIMETHYL ACETYLENEDICARBOXYLATE
3-COMPONENT REACTION
VINYLPHOSPHONIUM SALTS
TRIPHENYLPHOSPHINE
EFFICIENT
FACILE

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10.1002/ejoc.201900434

Glycoconjugates via Phosphorus YlidesFinal publisher's version, 1.21 MBLicence: Taverne

https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7451046/pdf/nihms-1029115.pdf

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CCDC 1888843: Experimental Crystal Structure Determination
Ghonchepour, E. (Contributor), Neochoritis, C. G. (Contributor), Kurpiewska, K. (Contributor), Kalinowska-Tłuścik, J. (Contributor), Islami, M. R. (Contributor) & Dömling, A. (Contributor), University of Groningen, 4-Jan-2019
DOI: 10.5517/ccdc.csd.cc21dhfd
Dataset
CCDC 1889525: Experimental Crystal Structure Determination
Ghonchepour, E. (Contributor), Neochoritis, C. G. (Contributor), Kurpiewska, K. (Contributor), Kalinowska-Tłuścik, J. (Contributor), Islami, M. R. (Contributor) & Dömling, A. (Contributor), University of Groningen, 8-Jan-2019
DOI: 10.5517/ccdc.csd.cc21f6f4
Dataset

Cite this

@article{ccb0603209f743238ea665124ee871bb,

title = "Glycoconjugates via Phosphorus Ylides",

abstract = "A facile, high yielding access to rare chimeric compounds combining phosphorus ylides with complex glycosyl formamides is described. We determined X-ray structures gaining structural insight into this compounds class. In addition, data mining of similar compounds deposited within the Cambridge Structural Database was performed. These derivatives could be used either as synthetic intermediates via the ylide functionalization and glyco chemical biology synthons or improving the pharmacokinetic properties of a potential bioactive molecule, exploiting the glycosyl moiety.",

keywords = "Phosphorus Ylides, Glycoconjugates, Glycosyl Formamides, Multi-Component Reactions, Chemical Biology, ONE-POT SYNTHESIS, ACETYLENIC ESTERS, DIMETHYL ACETYLENEDICARBOXYLATE, 3-COMPONENT REACTION, VINYLPHOSPHONIUM SALTS, TRIPHENYLPHOSPHINE, EFFICIENT, FACILE",

author = "Ehsan Ghonchepour and Neochoritis, {Constantinos G.} and Katarzyna Kurpiewska and Justyna Kalinowska-Tluscik and Islami, {Mohammad R.} and Alexander Domling",

year = "2019",

month = jun,

day = "16",

doi = "10.1002/ejoc.201900434",

language = "English",

volume = "2019",

pages = "3632--3635",

journal = "European Journal of Organic Chemistry",

issn = "1434-193X",

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

number = "22",

}

TY - JOUR

T1 - Glycoconjugates via Phosphorus Ylides

AU - Ghonchepour, Ehsan

AU - Neochoritis, Constantinos G.

AU - Kurpiewska, Katarzyna

AU - Kalinowska-Tluscik, Justyna

AU - Islami, Mohammad R.

AU - Domling, Alexander

PY - 2019/6/16

Y1 - 2019/6/16

N2 - A facile, high yielding access to rare chimeric compounds combining phosphorus ylides with complex glycosyl formamides is described. We determined X-ray structures gaining structural insight into this compounds class. In addition, data mining of similar compounds deposited within the Cambridge Structural Database was performed. These derivatives could be used either as synthetic intermediates via the ylide functionalization and glyco chemical biology synthons or improving the pharmacokinetic properties of a potential bioactive molecule, exploiting the glycosyl moiety.

AB - A facile, high yielding access to rare chimeric compounds combining phosphorus ylides with complex glycosyl formamides is described. We determined X-ray structures gaining structural insight into this compounds class. In addition, data mining of similar compounds deposited within the Cambridge Structural Database was performed. These derivatives could be used either as synthetic intermediates via the ylide functionalization and glyco chemical biology synthons or improving the pharmacokinetic properties of a potential bioactive molecule, exploiting the glycosyl moiety.

KW - Phosphorus Ylides

KW - Glycoconjugates

KW - Glycosyl Formamides

KW - Multi-Component Reactions

KW - Chemical Biology

KW - ONE-POT SYNTHESIS

KW - ACETYLENIC ESTERS

KW - DIMETHYL ACETYLENEDICARBOXYLATE

KW - 3-COMPONENT REACTION

KW - VINYLPHOSPHONIUM SALTS

KW - TRIPHENYLPHOSPHINE

KW - EFFICIENT

KW - FACILE

U2 - 10.1002/ejoc.201900434

DO - 10.1002/ejoc.201900434

M3 - Article

VL - 2019

SP - 3632

EP - 3635

JO - European Journal of Organic Chemistry

JF - European Journal of Organic Chemistry

SN - 1434-193X

IS - 22

ER -

Glycoconjugates via Phosphorus Ylides

Abstract

Keywords

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Datasets

CCDC 1888843: Experimental Crystal Structure Determination

CCDC 1889525: Experimental Crystal Structure Determination

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