169897-87-4Relevant academic research and scientific papers
Enantioselective Synthesis of the Sex Pheromone of Lichen Moth, Miltochrista calamine, and Its Diastereomer
Yuan, Gucheng,Liu, Jiawei,Yu, Shihang,Wang, Xueyang,Bian, Qinghua,Wang, Min,Zhong, Jiangchun
supporting information, p. 80 - 83 (2021/10/05)
The synthesis of a Miltochrista calamine sex pheromone and its diastereomer has been developed. The key steps of the synthetic approach involved Evans' chiral auxiliaries and the addition of alkyne to aldehyde, which were firstly applied to prepare this sex pheromone and its diastereomer. The synthetic sex pheromone could be used to trap insects and study physiological and ecological questions of the lichen moth.
Synthesis method of sex pheromone (S)-14-methyl-1-octadecene of lepidoptera pest peach leaf miners
-
, (2020/08/02)
The invention discloses a synthesis method of a sex pheromone (S)-14-methyl-1-octadecene of peach leaf miners, which comprises the following steps: carrying out ring opening on gamma-butyrolactone asa raw material, reacting the gamma-butyrolactone with benzyl chloride to generate 4-benzyloxybutyric acid, and reacting the 4-benzyloxybutyric acid with (S)-4-benzyl-2-oxazolidinone; performing reaction with methyl iodide under the action of organic base to induce chiral methyl; reducing the chiral methyl into alcohol under the action of lithium aluminum hydride, oxidizing the alcohol into aldehyde, and carrying out wittig reaction with triphenylpropylphosphonium bromide; after the Wittig reaction, using a Pt/C as a catalyst for catalytic hydrogenation to remove double bonds, removing benzyl with Pd/C as a catalyst to form alcohol, and oxidizing the alcohol into aldehyde; carrying out monobromination on 1, 10-decanediol, carrying out single protection by using TBSCl, and performing reaction with triphenylphosphine to obtain quaternary phosphonium salt; carrying out Wittig reaction on the aldehyde and the quaternary phosphonium salt, and using Pt/C as a catalyst for catalytic hydrogenation to eliminate double bonds; removing TBS single protection to form alcohol, and then oxidizing the alcohol into aldehyde; and reacting the aldehyde with methyltriphenylphosphonium bromide wittig toobtain the pheromone (S)-14-methyl-1-octadecene. According to the method, the reaction conditions are mild, chiral methyl is kept in the reaction process, and racemization is avoided.
A New Asymmetric Synthesis of (S)-14-Methyloctadec-1-ene, the Sex Pheromone of the Peach Leafminer Moth
Bai, Hongjin,Du, Zhen-Ting,He, Guo-Guo,Liu, Lu,Tang, Meng,Wei, Liang,Zhang, Tao
, p. 1089 - 1095 (2020/07/25)
Abstract: An asymmetric synthesis of 14-methyl-1-octadecene, the sex pheromone of thepeach leafminer moth has been achieved. Based on the asymmetric methylation ofchiral (S)-4-benzyloxazolidin-2-one, thecarbon chain of the target molecule was assembled through aC1+C10+C4+C3procedure. The γ-lactone was transformed into 4-(benzyloxy)butanoic acid andthen, with the induction of Evan’s template, a chiral methyl group wasintroduced to the position of the carboxylic group in 97percent de. After reduction and a couple of chemicaloperations, the designed key intermediate A1was obtained. The synthesis of another moiety was started from decane-1,10-diolwhich was selectively protected and oxidized. The long carbon chain wasinstalled according to a Wittig protocol. After deprotection, oxidization, andmethylenation, the target molecule was synthesized in 7 linear steps with anoverall yield of 30.3percent.
SYNUCLEINOPATHY THERAPEUTIC MEDICATION
-
Paragraph 0114; 0115; 0116; 0117, (2019/02/13)
This invention provides a pharmaceutical composition for treating or preventing synucleinopathy comprising a compound represented by formula (I), or a pharmaceutically acceptable salt thereof.
Linker Variation and Structure-Activity Relationship Analyses of Carboxylic Acid-based Small Molecule STAT3 Inhibitors
Lopez-Tapia, Francisco,Brotherton-Pleiss, Christine,Yue, Peibin,Murakami, Heide,Costa Araujo, Ana Carolina,Reis Dos Santos, Bruna,Ichinotsubo, Erin,Rabkin, Anna,Shah, Raj,Lantz, Megan,Chen, Suzie,Tius, Marcus A.,Turkson, James
, p. 250 - 255 (2018/03/21)
The molecular determinants for the activities of the reported benzoic acid (SH4-54), salicylic acid (BP-1-102), and benzohydroxamic acid (SH5-07)-based STAT3 inhibitors were investigated to design optimized analogues. All three leads are based on an N-met
2-ARYLSULFONAMIDO-N-ARYLACETAMIDE DERIVATIZED STAT3 INHIBITORS
-
, (2018/08/20)
The present disclosure provides pharmaceutical compositions comprising 2-arylsulfonamido-N-arylacetamide derivatized Stat3 inhibitors and certain pharmaceutically acceptable salts thereof, and methods of their use.
Stereoselective synthesis of the Paulownia bagworm sex pheromone
Sun, Zhi-Feng,Zhou, Lu-Nan,Zhang, Tao,Du, Zhen-Ting
, p. 558 - 562 (2017/06/19)
According to our retrosynthesis, the main chain of the target molecule could be constructed using a C5?+?C7?+?C5 strategy. The key induction reaction afforded chiral methyl group moieties using different Evans templates with different configurations. Li2CuCl4 was effectively employed in the Csp3[sbnd]Csp3 coupling protocol. The target molecular was obtained in a 12.6% overall yield with nine steps in the longest linear route.
TRIAZOLE-ISOXAZOLE COMPOUND AND MEDICAL USE THEREOF
-
Paragraph 3053; 3054, (2016/06/06)
A compound represented by Formula [I]: or pharmaceutically acceptable salt thereof, wherein each symbol is as defined in the description.
An expedient strategy towards an advanced pyrrolidine intermediate for the synthesis of pyrrolizidine alkaloids
Bera, Smritilekha,Mondal, Dhananjoy,Chatterjee, Bhaskar
supporting information, p. 1260 - 1262 (2015/09/22)
The asymmetric synthesis of a new pyrrolidine intermediate and a preceding amino triol derivative was accomplished using Crimmins' modified Evans aldol reaction as the key step. The synthetically useful pyrrolidine intermediate is expected to serve as the immediate precursor of biologically important pyrrolizidine alkaloids (-)-isoretronecanol and (-)-cremastrine. In addition, the amino triol subunit acts as a useful intermediate for the synthesis of oxocane heterocycles.
AMIDE COMPOUND AND MEDICINAL USE THEREOF
-
Page/Page column 64, (2013/02/27)
A compound of formula [I-W]: wherein each symbol is as defined in the description, or a pharmaceutically acceptable salt thereof.
