Regioselective Protection of the 4-Hydroxyl of 3,4-Dihydroxy-benzaldehyde

Plourde, Guy L.; Spaetzel, Randy R.

doi:10.3390/70900697

Cited by 22 publications

(11 citation statements)

References 17 publications

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“…These compounds were synthesized in three steps following a procedure similar to one that we have already published starting from the mono-protected benzaldehyde 6 (Plourde, G.L., 2002a;Plourde et al, 2002b;Plourde et al, 2005). Yields were comparable to those previously obtained in similar syntheses and are shown in Scheme 1.…”

Section: Resultsmentioning

confidence: 97%

Diastereoselective Spiroannulation of Phenolic Derivatives: Effect of Steric Hindrance on the Diastereoselectivity

Plourde

Susag²

2011

IJC

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This study was aimed at determining the effect, if any, that steric factors may have on the diastereoselectivity in the spiroannulation of simple phenols. A series of phenols bearing different size substituents ortho to the phenolic hydroxyl were synthesized and spiroannulated to the corresponding spiroethers in good to excellent yields (76-94%). However, the diastereoselectivity of the reaction remain mostly unchanged suggesting that stereoelectronic rather than steric factors influence the diastereoselectivity in this reaction.

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Section: Resultsmentioning

confidence: 97%

Diastereoselective Spiroannulation of Phenolic Derivatives: Effect of Steric Hindrance on the Diastereoselectivity

Plourde

Susag²

2011

IJC

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“…As the precursor of caffeic acid 3¢-sulfate 11, we used 4benzyloxy-3-hydroxybenzaldehyde 43. 31,32 The latter compound was sulfated with neopentyl chlorosulfate, to give the neopentyl sulfate ester 44 in 91% yield (Scheme 3). Attempts to debenzylate compound 44 using classical hydrogenation conditions (H 2 + 5% Pd/C), led to the reduction of the aldehyde functional group as well.…”

Section: Resultsmentioning

confidence: 99%

“…Following procedure E, 1.14 g (5 mmol) of 4-(benzyloxy)-3hydroxybenzaldehyde 43, 31,32 were dissolved in 25 mL of CH 2 Cl 2 . 1.14 g (7.5 mmol; 1.12 mL) of DBU and 1.52 g (7.5 mmol) of neopentylchlorosulfate 28, 30 were added successively under stirring at RT and nitrogen atmosphere.…”

Section: -(Benzyloxy)-5-formylphenyl Neopentyl Sulfate (44)mentioning

confidence: 99%

First synthesis, characterization, and evidence for the presence of hydroxycinnamic acid sulfate and glucuronide conjugates in human biological fluids as a result of coffee consumption

et al. 2010

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A systematic investigation of the human metabolism of hydroxycinnamic acid conjugates was carried out. A set of 24 potential human metabolites of coffee polyphenols has been chemically prepared, and used as analytical standards for unequivocal identifications. These included glucuronide conjugates and sulfate esters of caffeic, ferulic, isoferulic, m-coumaric and p-coumaric acids as well as their dihydro derivatives. A particular focus has been made on caffeic and 3,4-dihydroxyphenylpropionic acid derivatives, especially the sulfate conjugates, for which regioselective preparation was particularly challenging, and have so far never been identified as human metabolites. Ten out of the 24 synthesized conjugates have been identified in human plasma and/or urine after coffee consumption. A number of these conjugates were synthesized, characterized and detected as hydroxycinnamic acid metabolites for the first time. This was the case of dihydroisoferulic acid 3'-O-glucuronide, caffeic acid 3'-sulfate, as well as the sulfate and glucuronide derivatives of 3,4-dihydroxyphenylpropionic acid.

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“…The compounds (2 and 3) were successfully synthesized with yields in the range 44-48% (Scheme 2a). Compound 1 was synthesized according to the previously published procedure [28][29][30] by using different solvents and bases in the reactions.…”

Section: Synthesesmentioning

confidence: 99%

Syntheses, spectroscopic and crystallographic characterizations of 4-nitrobenzyloxy derivatives and benzofurans from ortho-substituted benzaldehydes and 4-nitrobenzyl bromide

et al. 2010

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A series of benzyloxybenzaldehyde derivatives (1-3) were prepared by the reactions of 4-nitrobenzyl bromide with 4-hydroxy-3-methoxybenzaldehyde (vanillin), 2-hydroxy-3-methoxybenzaldehyde (o-vanillin) and 2-hydroxy-4-methoxybenzaldehyde. When the reaction time is quite long, benzofuran derivatives (4 and 5) were obtained by the reactions of ortho-hydroxyaldehydes with the 4-nitrobenzyl bromide. Condensation reactions among the three benzyloxybenzaldehyde derivatives (1-3) with 2-aminomethylfuran (furfurylamine) yielded the new imine compounds (6-8). The structures of these aldehydes (1-3), benzofuran derivatives (4 and 5) and imine compounds (6-8) were confirmed on the basis of elemental analyses, IR, 1 H NMR and 13 C NMR and mass spectroscopy. The solid-state structures of compounds 4-6 were determined by single-crystal X-ray crystallography.

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Regioselective Protection of the 4-Hydroxyl of 3,4-Dihydroxy-benzaldehyde

Abstract: The regioselective protection of the 4-hydroxyl group of 3,4-dihydroxy-benzaldehyde was accomplished with seven different protecting groups (benzyl, p-methoxybenzyl, o-nitrobenzyl, 2,6-dichlorobenzyl, 3,4-dichlorobenzyl, vinyl and propargyl) in yields ranging between 67-75%.

Cited by 22 publications

References 17 publications

Diastereoselective Spiroannulation of Phenolic Derivatives: Effect of Steric Hindrance on the Diastereoselectivity

Diastereoselective Spiroannulation of Phenolic Derivatives: Effect of Steric Hindrance on the Diastereoselectivity

First synthesis, characterization, and evidence for the presence of hydroxycinnamic acid sulfate and glucuronide conjugates in human biological fluids as a result of coffee consumption

Syntheses, spectroscopic and crystallographic characterizations of 4-nitrobenzyloxy derivatives and benzofurans from ortho-substituted benzaldehydes and 4-nitrobenzyl bromide

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