812-01-1Relevant articles and documents
A Rapid and Mild Sulfation Strategy Reveals Conformational Preferences in Therapeutically Relevant Sulfated Xylooligosaccharides
Vo, Yen,Schwartz, Brett D.,Onagi, Hideki,Ward, Jas S.,Gardiner, Michael G.,Banwell, Martin G.,Nelms, Keats,Malins, Lara R.
supporting information, p. 9830 - 9838 (2021/06/01)
Although sulfated xylooligosaccharides are promising therapeutic leads for a multitude of afflictions, the structural complexity and heterogeneity of commercially deployed forms (e. g. Pentosan polysulfate 1) complicates their path to further clinical development. We describe herein the synthesis of the largest homogeneous persulfated xylooligomers prepared to date, comprising up to eight xylose residues, as standards for biological studies. Near quantitative sulfation was accomplished using a remarkably mild and operationally simple protocol which avoids the need for high temperatures and a large excess of the sulfating reagent. Moreover, the sulfated xylooligomer standards so obtained enabled definitive identification of a pyridinium contaminant in a sample of a commercially prepared Pentosan drug and provided significant insights into the conformational preferences of the constituent persulfated monosaccharide residues. As the spatial distribution of sulfates is a key determinant of the binding of sulfated oligosaccharides to endogenous targets, these findings have broad implications for the advancement of Pentosan-based treatments.
Efficient α-chlorination of carbonyl containing compounds under basic conditions using methyl chlorosulfate
Silva, Saúl,Maycock, Christopher D.
supporting information, p. 1233 - 1238 (2018/02/27)
An efficient method for the α-chlorination of ketones under basic conditions is described using methyl chlorosulfate. Its applicability for the chlorination of other functional groups has also been studied and it is equally useful for the synthesis of α-chloroesters and amides. Methyl chlorosulfate is described for the first time as a positive chlorine source. Some aldol reactions which occur during the chlorination of some substrates are also reported.
Method of manufacturing asymmetric imide ammonium salt (by machine translation)
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Paragraph 0051, (2019/01/07)
The corresponding phosphoric amide corresponding sulfonyl [to] further, tertiary ammonium salt method with good selectivity asymmetric imide. (2) Formula (3) represented by the formula [a] represented by the sulfonyl amide phosphate, organic reaction in the presence of base, formula (1) production of tertiary ammonium salts represented by the asymmetric imide. [R1 And R2 Are each independently a halogen group, an alkyl group, an alkoxy group or the like; (3) of the formula R2 The at least one halogen group; R3 The, the trimethylsilyl group or H; n is 1 or 2; M1 N + The, tertiary ammonium]Figure 1 [drawing] (by machine translation)
Synthesis, characterization and in vitro anti-tumor activities of matrine derivatives
Wang, Lisheng,You, Yejun,Wang, Songqing,Liu, Xu,Liu, Buming,Wang, Jinni,Lin, Xiao,Chen, Mingsheng,Liang, Gang,Yang, Hua
supporting information; experimental part, p. 4100 - 4102 (2012/07/14)
Nineteen previously unreported matrine derivatives were synthesized and characterized using elemental analysis, infrared spectroscopy, proton nuclear magnetic resonance spectroscopy, and mass spectrometry. Target compounds 6a-6l and 7a-7c showed stronger inhibitory activities than matrine in the in vitro antitumor tests and inhibited the growth of the Hep7402, B16-F10, A549, and TW03 cell lines. In addition, compound 6i exhibited a potent antitumor activity similar to that of colchicine.
Synthesis of Sterically Hindered Secondary Aminoether Alcohols
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Page/Page column 6, (2010/11/28)
Severely sterically hindered secondary aminoether alcohols are prepared by reacting an organic carboxylic acid or alkali metal salt of an organic carboxylic acid with a sulfonyl halide, a sulfuryl halide, a mixed sulfuryl ester halide or a mixed sulfuryl amide halide to yield a sulfonic-carboxylic anhydride compound which is then reacted with a dioxane to cleave the ring of the dioxane, yielding a cleavage product which cleavage product is then aminated with an alkylamine and hydrolyzed with base to yield the severely sterically hindered secondary aminoether alcohol.
Chloromethyl chlorosulfate: A new, catalytic method of preparation and reactions with some nucleophiles
Power, Nicholas P.,Bethell, Donald,Proctor, Lee,Latham, Elliot,Dawson, Paul
, p. 1554 - 1562 (2007/10/03)
A catalytic method of preparing chloromethyl chlorosulfate (CMCS) was described. The reaction of liquid SO3 with CH2Cl 2 at room temperature led to SO3 insertion into the C-Cl bonds, giving CMCS. The product mixtures consists entirely of CMCS and the product of further sulfation, methylene bis(chlorosulfate) (MBCS). The reaction was shown to be first order in the catalyst and third order in SO3 by measuring initial rates of CMCS formation or total CH2Cl2 consumption. The results show that the reaction between dichloromethane and SO3 at room temperature is accelerated by very low concentrations.
Process for functionalising a phenolic compound carrying an electron-donating group
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, (2008/06/13)
The invention concerns a method for functionalizing a phenolic compound bearing an electron-donor group, in said group para position, inter alia a method for the amidoalkylation of a phenolic compound bearing an electron-donor group, and more particularly, a phenolic compound bearing an electron-donor group preferably, in the hydroxyl group ortho position. The method for functionalizing in para position with respect to an electron-donor group carried by a phenolic compound is characterised in that the phenolic compound bearing an electron-donor group is subjected to the following steps: a first step which consists of protecting the hydroxyl group in the form of a sulphonic ester function; a second step which consists in reacting the protected phenolic compound with an electrophilic reagent; optionally, a third step deprotecting the hydroxyl group.
