2,4,5-Tri-O-methylhiascic acid
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| Category | Others |
| Catalog number | BBF-05586 |
| CAS | 79786-35-9 |
| Molecular Weight | 526.49 |
| Molecular Formula | C27H26O11 |
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Description
It is a new depside isolated from the lichen Parmelia damaziana.
Specification
| IUPAC Name | 2-hydroxy-4-((2-hydroxy-6-methyl-4-((3,4,6-trimethoxy-2-methylbenzoyl)oxy)benzoyl)oxy)-6-methylbenzoic acid |
Reference Reading
1. Bacterial battle against acidity
Julia Schwarz, Kilian Schumacher, Sophie Brameyer, Kirsten Jung FEMS Microbiol Rev. 2022 Nov 2;46(6):fuac037. doi: 10.1093/femsre/fuac037.
The Earth is home to environments characterized by low pH, including the gastrointestinal tract of vertebrates and large areas of acidic soil. Most bacteria are neutralophiles, but can survive fluctuations in pH. Herein, we review how Escherichia, Salmonella, Helicobacter, Brucella, and other acid-resistant Gram-negative bacteria adapt to acidic environments. We discuss the constitutive and inducible defense mechanisms that promote survival, including proton-consuming or ammonia-producing processes, cellular remodeling affecting membranes and chaperones, and chemotaxis. We provide insights into how Gram-negative bacteria sense environmental acidity using membrane-integrated and cytosolic pH sensors. Finally, we address in more detail the powerful proton-consuming decarboxylase systems by examining the phylogeny of their regulatory components and their collective functionality in a population.
2. Recent advances in the synthesis of 4'-truncated nucleoside phosphonic acid analogues
Guang Huan Shen, Joon Hee Hong Carbohydr Res. 2022 Mar;513:108517. doi: 10.1016/j.carres.2022.108517. Epub 2022 Feb 7.
The synthesis of five series of 4'-truncated nucleoside phosphonic acid analogues is discussed in this review: (1) 4'-truncated furanose nucleoside phosphonic acid analogues; (2) 4'-truncated pyrrolidine nucleoside phosphonic acid analogues; (3) 4'-truncated carbocyclic nucleoside phosphonic acid analogues; (4) 4'-truncated isoxazole nucleoside phosphonic acid analogues; (5) 4'-truncated miscellaneous nucleoside phosphonic acid analogues. Five different ways are used to make the phosphonate moiety: (i) Michaelis-Arbuzov reaction of RX (X = Br, I, OTf) with trialkyl phosphate; (ii) Lewis acid catalyzed Michaelis-Arbuzov reaction of glycoside with trialkyl phosphite; (iii) nucleophilic addition of a dialkyl phosphite to a carbonyl group; (iv) direct coupling reaction with amino alkyl phosphonate; (v) de novo synthesis of phosphonated-isoxazole and 1,3-dioxolane heterocycles from phosphonated starting materials. Their biological activity results are briefly discussed.
3. N1/N4 1,4-Cycloaddition of 1,2,4,5-Tetrazines with Enamines Promoted by the Lewis Acid ZnCl2
Zixi Zhu, Dale L Boger J Org Chem. 2022 May 6;87(9):6288-6301. doi: 10.1021/acs.joc.2c00543. Epub 2022 Apr 13.
The second example of selective N1/N4 1,4-cycloaddition (vs C3/C6 1,4-cycloaddition) of 1,2,4,5-tetrazines with preformed or in situ generated enamines now promoted by the Lewis acid ZnCl2 and with an expanded scope is described. The reaction constitutes a formal [4 + 2] cycloaddition across two nitrogen atoms (N1/N4 vs C3/C6) of a 1,2,4,5-tetrazine followed by retro [4 + 2] cycloaddition loss of a nitrile and aromatization to provide 1,2,4-triazines. Optimization of reaction parameters, simplification of its implementation through in situ enamine generation from ketones, definition of the enamine reaction scope for 3,6-bis(thiomethyl)-1,2,4,5-tetrazine, exploration of the 1,2,4,5-tetrazine scope, and representative applications of the product 1,2,4-triazines are detailed. The work establishes and further extends a powerful method for efficient one-step regioselective synthesis of 1,2,4-triazines under mild reaction conditions directly now from easily accessible ketones. It extends the substrate scope of a solvent (hexafluoroisopropanol) hydrogen bonding-promoted reaction that we recently reported with aryl-conjugated enamines, permitting the use of simple ketone-derived enamines and expanding the generality of the remarkable reaction. The reaction is regioselective with respect to the site of reaction with unsymmetrical ketones and provides exclusively a single 1,2,4-triazine regioisomer consistent with our previously established stepwise mechanism of formal N1/N4 1,4-cycloaddition, overcoming the challenges observed in conventional approaches to 1,2,4-triazines.
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Bio Calculators
* Our calculator is based on the following equation:
Concentration (start) x Volume (start) = Concentration (final) x Volume (final)
It is commonly abbreviated as: C1V1 = C2V2
* Total Molecular Weight:
g/mol
Tip: Chemical formula is case sensitive. C22H30N4O √ c22h30n40 ╳
