4049-39-2Relevant articles and documents
Fluoroethoxylanin as well as preparation method and application thereof
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Paragraph 0045; 0068-0072, (2021/10/20)
The invention relates to fluoroethoxylanin as well as a preparation method and application thereof. The preparation method comprises the following steps: firstly, 3,4 -hydroxybenzaldehyde and benzyl chloride serve as raw materials, and 3 -hydroxy -4 -benzyloxybenzaldehyde is prepared. The product is reacted with bromomethyl methyl ether, and the product is sequentially subjected Wittig reaction, reduction reaction and alkylation reaction, and the obtained product is reacted with p-toluenesulfonic acid chloride to obtain fifth intermediate. Finally fifth intermediate and complexing agent K are added. 2.2.2 . Reaction of potassium fluoride and acidification of the product gave the above fluoroethoxylanolin. Compared with the prior art, the fluoroethoxylanin prepared by the invention can reflect the distribution of the tracer in the local tissue of the organism, thereby visualizing the tumors, and providing the metabolic information targeting metabolic pathway types and.
Synthesis of a Photo-Caged DOPA Derivative by Selective Alkylation of 3,4-Dihydroxybenzaldehyde
Schneider, Tobias,Kubyshkin, Vladimir,Budisa, Nediljko
, p. 2053 - 2063 (2018/05/31)
Natural and synthetic polymers containing the catechol moiety of noncoded amino acid 3,4-dihydroxyphenylalanine (DOPA) are capable of metal-coordination and adhesion under wet conditions. Masking the catechol subunit with a photo-cleavable group would provide an opportunity to design tunable adhesion properties that are especially important for biomaterial and biomedicine applications. Herein, we report the regioselective synthesis of a photo-caged DOPA bearing an ortho-nitrobenzyl (oNB) group that is capable of undergoing cleavage upon irradiation with UV light. We developed a selective synthetic route towards a 3-O-oNB alkylated DOPA regioisomer that can be readily incorporated into proteins by using a previously developed bio-expression platform. The synthesis is based on a regioselectivity switch in 3,4-dihydrozybenzaldehyde alkylation upon application of different equivalents of deprotonating base. The enantiomerically pure 3-O-oNB-DOPA was prepared on a gram scale and proved to be generally compatible with the solid-phase peptide synthesis conditions. We also demonstrate the general applicability of the developed synthetic strategy by providing the synthesis of 3-O-methyl-DOPA.
Generation of Benzyne Species from Diphenylphosphoryl Derivatives: Simultaneous Exchange of Three Functional Groups
Gorobets, Evgueni,Parvez, Masood,Derksen, Darren J.,Keay, Brian A.
supporting information, p. 8479 - 8482 (2016/07/11)
Interaction of (2-diphenylphosphoryl-3-iodo-4-methoxy-phenyl) methanol with NaH in DMF at ambient temperature results in the generation of benzyne intermediates that can be trapped by furan or DMF. Trapping with DMF forms 3-(dimethylaminomethyl)-2-hydroxy-6-methoxybenzaldehyde demonstrating the simultaneous exchange of three functionalities in a single step. The presence of the alkoxy substituent adjacent to iodine is critical for high regioselectivity addition of DMF. The corresponding bromide or triflate can be used in place of the iodide with equal efficiency. This methodology was used to synthesize the reported structure of gigasol and leading to a structural reassignment of this biscoumarin natural product.
