34904-92-2Relevant academic research and scientific papers
Photoinduced Release of a Chemical Fuel for Acid–Base-Operated Molecular Machines
Biagini, Chiara,Di Pietri, Flaminia,Mandolini, Luigi,Lanzalunga, Osvaldo,Di Stefano, Stefano
, p. 10122 - 10127 (2018)
Back and forth motions of the acid–base-operated molecular switch 1 are photo-controlled by irradiation of a solution, which also contains the photolabile pre-fuel 4. The photo-stimulated deprotection of the pre-fuel produces controlled amounts of acid 2,
Wavelength-orthogonal photolysis of neurotransmitters in vitro
Stanton-Humphreys, Megan N.,Taylor, Ruth D. T.,McDougall, Craig,Hart, Mike L.,Brown, C. Tom A.,Emptage, Nigel J.,Conway, Stuart J.
, p. 657 - 659 (2012/02/02)
Irradiation of a mixture of 4-methoxyphenacyl-caged (S)-glutamate and 4,5-dimethoxy-2-nitrobenzyl-caged γ-amino butyric acid (GABA) on neurons, at ～260 nm, evokes selective photorelease of (S)-glutamate (Glu) whereas photolysis at 405 nm causes selective photorelease of GABA.
A time-resolved spectroscopic study of the bichromophoric phototrigger 3',5'-dimethoxybenzoin diethyl phosphate: Interaction between the two chromophores determines the reaction pathway
Chensheng, Ma.,Kwok, Wai Ming,An, Hui-Ying,Guan, Xiangguo,Fu, Michael Yunyi,Toy, Patrick H.,Phillips, David Lee
supporting information; experimental part, p. 5102 - 5118 (2010/08/05)
3',5'-Dimethoxybenzoin (DMB) is a bichromophoric system that has widespread application as a highly efficient photoremovable protecting group (PRPG) for the release of diverse functional groups. The photodeprotection of DMB phototriggers is remarkably cle
A convenient and selective synthesis of unsymmetrical benzoins via the cyanide ion catalyzed cleavage of benzils
Demir, Ayhan S.,Reis, ?mer
, p. 3803 - 3811 (2007/10/03)
The cyanide ion-catalyzed cleavage of benzils is used for the generation of various 'masked' acyl intermediates. The reaction of these intermediates with various aldehydes furnishes the corresponding esters of unsymmetrical benzoins in very good yields. A variety of unsymmetrical benzoin derivatives are synthesized in this way, including ferrocene derivatives. The hydrolysis of benzoin esters and their subsequent oxidation affords the corresponding unsymmetrical benzoins and benzils in high yield.
Wavelength-controlled orthogonal photolysis of protecting groups
Blanc, Aurelien,Bochet, Christian G.
, p. 5567 - 5577 (2007/10/03)
The selective control of a chemical process by the use of an electromagnetic wave has been a challenging goal for several decades. In this article, we describe for the first time the use of a monochromatic light beam to differentiate two different reactive centers. A direct application of this concept is found in the chemistry of protecting groups. Two different photolabile protecting groups were tuned to be responsive to a specific wavelength (e.g., 254 or 420 nm). Using derivatives of the 2-nitroveratryl fragment (such as 10, sensitive at 420 nm) and 3′,5′-dimethoxybenzoin fragment (such as 4, sensitive at 254 nm), it was shown that energy transfer phenomena did not erode the selectivity. Both the inter- and the intramolecular cases were studied and showed selectivities within the synthetically useful range. Hence, we could replace the traditional chemical orthogonality by a chromatic orthogonality.
Photogeneration of amines from α-keto carbamates: Design and preparation of photoactive compounds
Cameron, James F.,Willson, C. Grant,Frechet, Jean M. J.
, p. 2429 - 2442 (2007/10/03)
The design and synthesis of substituted desyl (2-oxo-1,2-diphenylethyl) groups has been investigated to create new photolabile protecting groups. The photoreactivity of these chromophores stems from the diverse photochemistry of the desyl group. Several chromophore designs have been explored in which the substitution pattern of the parent desyl chromophore was varied systematically. The required benzoin chromophores are prepared by a variety of synthetic routes, depending on the structure of the benzoin chromophore desired. Symmetrical benzoins are readily available via the benzoin condensation. Unsymmetrical benzoins including 2,2-disubstituted α-hydroxy ketones are generally prepared via trimethylsilyl (TMS) masked cyanohydrins. On reaction with a Grignard reagent, the TMS masked cyanohydrin functions as an α-hydroxycarbonyl equivalent to form α-hydroxy ketones. Alternatively, lithiation of a TMS masked cyanohydrin generates a benzoyl anion equivalent which reacts with aldehydes and ketones to generate substituted benzoins. These desyl chromophores have significant potential as new photolabile protecting moieties for a variety of functional groups and are used to mask primary and secondary amines as photosensitive α-keto carbamates. The substituted benzoin carbamates are readily prepared from the appropriate benzoin by reaction with isocyanates or by activation as a mixed carbonate followed by reaction with the free amine. These α-keto carbamates are interesting for two main reasons. First, the facile synthesis of these materials indicates the ease of introduction of the desyl based photolabile group. Second, these α-keto carbamates may be used for rapid evaluation of novel photoactive desyl based chromophores.
Efficient synthesis of photolabile alkoxy benzoin protecting groups
Stowell, Michael H.B.,Rock, Ronald S.,Rees,Chan, Sunney I.
, p. 307 - 310 (2007/10/02)
An effective implementation of the Corey-Seebach dithiane addition for the synthesis of photolabile alkoxy benzoin adducts is reported. The method allows for the facile synthesis of photolabile 3',5'-dimethoxybenzoin protected compounds in near quantitati
Photoremovable Protecting Groups for Phosphorylation of Chiral Alcohols. Asymmetric Synthesis of Phosphotriesters of (-)-3',5'-Dimethoxybenzoin
Pirrung, Michael C.,Shuey, Steven W.
, p. 3890 - 3897 (2007/10/02)
Procedures have been developed for the preparation of dimethoxybenzoinyl (DMB) phosphate triesters that can be deprotected photochemically.These compounds can be useful in light-directed synthesis and caging.The photochemistry of a wide variety of fluorine-, oxygen-, and nitrogen-substituted benzoin acetates was examined to determine the substitution pattern in the nonacylated aromatic ring producing optimum chemical yields.Two groups, 2',3'-dimethoxybenzoin and 3',5'-dimethoxybenzoin, were found to give the highest yields of the benzofuran product and were further developed for the photochemical deprotection of phosphate esters.These reactions could not be quenched, suggesting a singlet photosolvolysis mechanism.An asymmetric synthesis of 3',5'-dimethoxybenzoin via the benzaldehyde cyanohydrin was developed that minimizes the number of diastereomers formed in the phosphorylation of chiral alcohols.A phosphoramidite reagent for the derivatization of alcohols was prepared and used to produce scalemic dimethoxybenzoinyl phosphate esters from pantolactone and glycerol, serine, and tyrosine derivatives.These compounds were deprotected photochemically to produce the phosphodiesters in high yield.
Synthetic, Mechanistic and Photochemical Studies of Phosphate Esters of Substituted Benzoins
Corrie, John E. T.,Trentham, David R.
, p. 2409 - 2418 (2007/10/02)
Synthesis of the phosphate esters of several benzoins, variously substituted with methoxy groups in one or both aromatic rings, proceeds via the corresponding cyclic ethylene ketals.These are phosphitylated with bis(2-cyanoethyl) diisopropylphosphoramidit
