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1 article(s) from Yousef, Abraham L

Photorelease of phosphates: Mild methods for protecting phosphate derivatives

Sanjeewa N. Senadheera,
Abraham L. Yousef and
Richard S. Givens

Beilstein J. Org. Chem. 2014, 10, 2038–2054, doi:10.3762/bjoc.10.212

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Graphical Abstract

Figure 1: Common photoremovable protecting groups (PPGs) for phosphates depicted as diethyl phosphate (DEP) e...

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Scheme 1: Synthesis of 2,6-HNA DEP (10), 1,4-HNA DEP (14a), and 1,4-MNA DEP (14b) DEP esters. Reagents and co...

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Scheme 2: Synthesis of diethyl 8-(benzyloxy)quinolin-5-yl)-2-oxoethyl phosphate (5,8-BQA DEP, 24). Reagents a...

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Figure 2: A. UV–vis spectrum of 14a (1,4-HNA DEP) in 1% aq MeCN. B. Fluorescence emission/excitation spectra ...

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Scheme 3: Photolysis of 1,4-HNA and 1,4-MNA diethyl phosphates 14a and 14b in aq MeOH.

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Scheme 4: The photo-Favorskii rearrangement of 14a.

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Scheme 5: Photolysis of 2,6-HNA DEP (10) in 1% aq MeCN.

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Scheme 6: Photolysis of 5,8-BQA diethyl phosphate (24).

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Figure 3: Naphthyl and quinolin-5-yl caged phosphate esters 10, 14, 24 and 27 (acetate ester).

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Figure 4: Previously studied caged diethyl phosphate PPGs possessing aromatic (benzyl, phenacyl, and naphthyl...

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Scheme 7: Photo-Favorskii mechanism based on pHP DEP 4a photochemistry as applied to 1,4-HNA DEP (14a).

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Scheme 8: Photodehydration and substitution of 5-(1-hydroxyethyl)-1-naphthol 34 [19].

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Scheme 9: Putative rearrangement intermediates for 1,5- and 2,6- HNA chromophores.

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Published 29 Aug 2014

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