Photoinduced electron-transfer α-deoxygenation of aldonolactones. Efficient synthesis of 2-deoxy-d-arabino-hexono-1,4-lactone

Bordoni, Andrea; Lederkremer, Rosa M. de; Marino, Carla

doi:10.1016/j.carres.2006.04.012

Cited by 14 publications

(6 citation statements)

References 19 publications

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“…5B). 151 We applied the procedure to d -galactono and d -glucono-1,4-lactone derivatives with good results in all the cases (Scheme 26B and C). The unique reactivity of the aldonolactone allowed for the MCZ to turn over and we used it in 10 mol%.…”

Section: Deoxygenation Methodsmentioning

confidence: 97%

“…149 Thus, we easily prepared derivative 59 , and to our surprise we observed that only few minutes of irradiation were necessary to complete the PET reaction (Scheme 26A). 150,151 The effectiveness of the reaction on lactone derivatives, in comparison to non lactonic esters that required several hours of irradiation for deoxygenation, was attributed to the stabilization of the intermediate radical vi by the vicinal carbonyl lactone group (Fig. 5B).…”

Section: Deoxygenation Methodsmentioning

confidence: 99%

“…The unique reactivity of the aldonolactone allowed for the MCZ to turn over and we used it in 10 mol%. 151…”

Section: Deoxygenation Methodsmentioning

confidence: 99%

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Deoxy sugars. General methods for carbohydrate deoxygenation and glycosidation

Marino

Bordoni

2022

Org. Biomol. Chem.

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Section: Deoxygenation Methodsmentioning

confidence: 97%

Section: Deoxygenation Methodsmentioning

confidence: 99%

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Deoxy sugars. General methods for carbohydrate deoxygenation and glycosidation

Marino

Bordoni

2022

Org. Biomol. Chem.

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“…Visible‐light mediated photoredox catalysis is an active area of research that aims at the development of safer and environmentally friendly protocols for radical reactions . Photocatalytic defunctionalizations represent one important class of reactions with broad applicability, ranging from biofuel to (bio)material production . We also have contributed to these areas by developing visible‐light mediated protocols for the deoxygenation of alcohols and halides .…”

Section: Introductionmentioning

confidence: 99%

Visible‐light photoredox‐catalyzed desulfurization of thiol‐ and disulfide‐containing amino acids and small peptides

Lee

Neukirchen

Cabrele

et al. 2017

Journal of Peptide Science

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A scalable protocol for the desulfurization of cysteine by using visible light, the photocatalyst Ir(dF(CF )ppy) (dtb-bpy)PF and triethylphosphite under biphasic reaction conditions has been developed. The loading of the catalyst can be as low as 0.01 mol%, which can be efficiently removed during the workup (≤0.3 ppm), giving rise to the corresponding desulfurized product in high yields. This method has been applied also to cystine, penicillamine, and reduced and oxidized glutathione. The desulfurization has been found to be pH sensitive, with an optimal pH value of 6.5 and 7.0 for the cysteine derivatives and glutathione, respectively. In addition, during the desulfurization of a decapeptide containing cysteine and methionine, concurrent oxidation of the two sulfur-containing residues to disulfide and sulfoxide has been observed. Therefore, whereas the presented protocol allows a straightforward visible light-mediated desulfurization of simple thiols by using very low catalyst loading and a cost-effective trialkylphosphite as thiyl radical trapping agent, its application to complex substrates needs to be carefully validated. Copyright © 2017 European Peptide Society and John Wiley & Sons, Ltd.

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“…3). [28][29][30][31][32] We have contributed to the synthesis of galactofuranosyl precursors 32,33 and the development of and new glycosylation methodologies. 28,33 We have also synthesized radioactive substrates (4 * and 5 * ) which were used for studies on the galactofuranosidase 21,23 and on the galactofuranosyltransferase.…”

Section: Introductionmentioning

confidence: 99%