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2 article(s) from Eguaogie, Olga

Mechanochemistry of nucleosides, nucleotides and related materials

Olga Eguaogie,
Joseph S. Vyle,
Patrick F. Conlon,
Manuela A. Gîlea and
Yipei Liang

Beilstein J. Org. Chem. 2018, 14, 955–970, doi:10.3762/bjoc.14.81

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Graphical Abstract

Figure 1: Examples of equipment used to perform mechanochemistry on nucleoside and nucleotide substrates (not...

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Figure 2: Ganciclovir.

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Scheme 1: Nucleoside tritylation effected by hand grinding in a heated mortar and pestle.

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Scheme 2: Persilylation of ribonucleoside hydroxy groups (and in situ acylation of cytidine) in a MBM.

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Scheme 3: Nucleoside amine and carboxylic acid Boc protection using an improvised attritor-type mill.

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Scheme 4: Nucleobase Boc protection via transient silylation using an improvised attritor-type mill.

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Scheme 5: Chemoselective N-acylation of an aminonucleoside using LAG in a MBM.

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Scheme 6: Azide–alkyne cycloaddition reactions performed in a copper vessel in a MBM.

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Figure 3: a) Custom-machined copper vessel and zirconia balls used to perform CuAAC reactions (showing: upper...

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Scheme 7: Thiolate displacement reactions of nucleoside derivatives in a MBM.

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Scheme 8: Selenocyanate displacement reactions of nucleoside derivatives in a MBM.

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Scheme 9: Nucleobase glycosidation reactions and subsequent deacetylation performed in a MBM.

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Scheme 10: Regioselective phosphorylation of nicotinamide riboside in a MBM.

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Scheme 11: Preparation of nucleoside phosphoramidites in a MBM using ionic liquid-stabilised chlorophosphorami...

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Scheme 12: Preparation of a nucleoside phosphite triester using LAG in a MBM.

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Scheme 13: Internucleoside phosphate coupling linkages in a MBM.

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Scheme 14: Preparation of ADPR analogues using in a MBM.

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Scheme 15: Synthesis of pyrophosphorothiolate-linked dinucleoside cap analogues in a MBM to effect hydrolytic ...

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Figure 4: Early low temperature mechanised ball mill as described by Mudd et al. – adapted from reference [78].

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Scheme 16: Co-crystal grinding of alkylated nucleobases in an amalgam mill (N.B. no frequency was recorded in ...

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Figure 5: Materials used to prepare a smectic phase.

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Figure 6: Structures of 5-fluorouracil (5FU) and nucleoside analogue prodrugs subject to mechanochemical co-c...

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Scheme 17: Preparation of DNA-SWNT complex in a MBM.

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Review

Published 27 Apr 2018

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Nucleophilic displacement reactions of 5′-derivatised nucleosides in a vibration ball mill

Olga Eguaogie,
Patrick F. Conlon,
Francesco Ravalico,
Jamie S. T. Sweet,
Thomas B. Elder,
Louis P. Conway,
Marc E. Lennon,
David R. W. Hodgson and
Joseph S. Vyle

Beilstein J. Org. Chem. 2017, 13, 87–92, doi:10.3762/bjoc.13.11

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Graphical Abstract

Scheme 1: Model reactions of 5′-chloro-5′-deoxyadenosine (1a) with 4-methoxybenzylthiolate salts used to opti...

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Scheme 2: Thiolate displacement reactions of 5′-derivatised nucleosides using VBM.

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Scheme 3: Selenocyanate displacement reactions of 5′-derivatised nucleosides using liquid-assisted grinding (...

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Full Research Paper

Published 13 Jan 2017

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