81389-85-7Relevant academic research and scientific papers
Copper(ii)-catalyzed stereoselective 1,2-addition: Vs. Ferrier glycosylation of "armed" and "disarmed" glycal donors
Gurawa, Aakanksha,Kashyap, Sudhir,Kumar, Manoj,Reddy, Thurpu Raghavender
, p. 4848 - 4862 (2020/07/13)
Selective activation of "armed' and "disarmed"glycal donors enabling the stereo-controlled glycosylations by employing Cu(ii)-catalyst as the promoter has been realized. The distinctive stereochemical outcome in the process is mainly influenced by the presence of diverse protecting groups on the donor and the solvent system employed. The protocol is compatible with a variety of aglycones including carbohydrates, amino acids, and natural products to access deoxy-glycosides and glycoconjugates with high α-anomeric selectivity. Notably, the synthetic practicality of the method is amply verified for the stereoselective assembling of trisaccharides comprising 2-deoxy components. Mechanistic studies involving deuterated experiments validate the syn-diastereoselective 1,2-addition of acceptors on the double bond of armed donors.
Robust perfluorophenylboronic acid-catalyzed stereoselective synthesis of 2,3-unsaturated O-, C-, N- And S-linked glycosides
Tatina, Madhu Babu,Mengxin, Xia,Peilin, Rao,Judeh, Zaher M. A.
supporting information, p. 1275 - 1280 (2019/07/08)
A convenient protocol was developed for the synthesis of 2,3-unsaturated C-, O-, N- and S-linked glycosides (enosides) using 20 mol % perflurophenylboronic acid catalyst via Ferrier rearrangement. Using this protocol, D-glucals and L-rhamnals reacted with various C-, O-, N- and S-nucleophiles to give a wide range of glycosides in up to 98% yields with mainly α-anomeric selectivity. The perflurophenylboronic acid successfully catalyzed a wide range of substrates (both glucals and nucleophiles) under very mild reaction conditions.
A Highly Efficient Magnetic Iron(III) Nanocatalyst for Ferrier Rearrangements
Chen, Heshan,Ding, Zekun,Dong, Youxian,Guo, Hong,Jiang, Nan,Qiu, Saifeng,Xu, Xiaoxia,Zhang, Jianbo,Zhou, Le
supporting information, p. 1419 - 1426 (2019/07/15)
A novel and highly efficient magnetic Fe 3 O 4 &at;C&at;Fe(III) core-shell catalyst, in which the carbon shell was prepared from lotus leaf, was fabricated. This nanocatalyst was successfully applied in the synthesis of a series of 2,3-unsaturated O- glycosides in excellent yields and with high selectivity, especially in the case of 2-halo O- glycosides, which differ in reactivity from nonsubstituted O- glycosides, but which have scarcely been explored before. Moreover, the catalyst could be easily separated from the reaction by the application of an external magnetic force and reused a minimum of five times without any significant decrease in the yields of the products. In addition, the reaction proceeded readily on a gram scale, which provides a bright prospect for future applications.
Substrate-Controlled Direct α-Stereoselective Synthesis of Deoxyglycosides from Glycals Using B(C6F5)3 as Catalyst
Sau, Abhijit,Palo-Nieto, Carlos,Galan, M. Carmen
, p. 2415 - 2424 (2019/02/26)
B(C6F5)3 enables the metal-free unprecedented substrate-controlled direct α-stereoselective synthesis of deoxyglycosides from glycals. 2,3-Unsaturated α-O-glycoside products are obtained with deactivated glycals at 75 °C in the presence of the catalyst, while 2-deoxyglycosides are formed using activated glycals that bear no leaving group at C-3 at lower temperatures. The reaction proceeds in good to excellent yields via concomitant borane activation of glycal donor and nucleophile acceptor. The method is exemplified with the synthesis of a series of rare and biologically relevant glycoside analogues.
Montmorillonite-catalyzed glysosylation of alcohols with glycals derived from galactose and glucose under microwave-induced reactions
Yadav, Ram Naresh,Banik, Indrani,Banik, Bimal Krishna
, p. 1385 - 1387 (2020/06/27)
Montmorillonite K10-catalyzed glycosylation of alcohols with glycals obtained from galactose and glucose is performed efficiently using microwave irradiation with good anomeric selectivity.
Structure-based design, synthesis and antitumoral evaluation of enulosides
Santos, Jonh A.M.,Santos, Cosme S.,Almeida, Claudia L.A.,Silva, Thiago D.S.,Freitas Filho, Jo?o R.,Milit?o, Gardenia C.G.,da Silva, Teresinha G.,da Cruz, Carlos H.B.,Freitas, Juliano C.R.,Menezes, Paulo H.
, p. 192 - 201 (2017/02/15)
Enulosides, carbohydrate derivatives containing an α,β-unsaturated carbonyl unit, were designed and obtained in high yields and isomeric purity. All synthesized compounds exhibited antitumoral activity in micromolar range against four tested tumor cells lines, being the best results observed for HL-60?cells. These compounds open new possibilities to prepare an array of more active, site-specific or selective antitumor agents. 2016 Elsevier Ltd. All rights reserved.
Hafinium (IV) promoted synthesis of 2,3-unsaturated N- and C-pseudoglycosides via Type I Ferrier Rearrangement
Chen, Peiran,Zhang, Xiaoying
, p. 309 - 312 (2017/01/03)
By using Hf(OTf)4as the catalyst, a series of 2,3-N- and C-unsaturated-glucosides have been synthesized from 3,4,6-tri-O-acetyl-D-glucal, 2,4,6-tri-O-benzyl-D-glucal and ((2R,3S)-3-acetoxy-2,3-dihydrofuran-2-yl)methyl acetate under mild reaction conditions in good yields with high anomeric selectivities.
Palladium-Catalyzed α-Stereoselective O-Glycosylation of O(3)-Acylated Glycals
Sau, Abhijit,Galan, M. Carmen
supporting information, p. 2857 - 2860 (2017/06/07)
Pd(MeCN)2Cl2 enables the α-stereoselective catalytic synthesis of 2,3-unsaturated O-glycosides from O(3)-acylated glycals without the requirement for additives to preactivate either donor or nucleophile. Mechanistic studies suggest that, unlike traditional (η3-allyl)palladium-mediated processes, the reaction proceeds via an alkoxy-palladium intermediate that increases the proton acidity and oxygen nucleophilicity of the alcohol. The method is exemplified with the synthesis of a range of glycosides and glycoconjugates of synthetic utility.
Synthesis of anti-inflammatory 2,3-unsaturated O-glycosides using conventional and microwave heating techniques
De Melo, Adriana Cristina N.,De Oliveira, Ronaldo N.,De Freitas Filho, Joao R.,Da Silva, Teresinha G.,Srivastava, Rajendra M.
, p. 205 - 211 (2017/07/22)
The preparation of eight 2,3-unsaturated O-glycosides from D-glycals and alcohols, using montmorillonite K-10 as an acid catalyst, is described. The Ferrier rearrangement products were obtained in good yields using conventional heating and microwave irradiation but the reaction time was substantially reduced employing the latter procedure. The yields were slightly lower under microwave exposure. Five of the di-O-acetylated products were deacetylated to the glycosides in excellent yields. The acetylated products possess good antiinflammatory property suggesting that the acetyl group plays an important role in reducing the inflammation. Among the compounds tested, glycosides containing thiophene as an aglycone present much better inflammation reducing characteristics than the analogues without this function.
Magnetic core-shell Fe3O4@C-SO3H as an efficient and renewable 'Green catalyst' for the synthesis of O-2,3-unsaturated Glycopyra-nosides
Sun, Guosheng,Qiu, Saifeng,Ding, Zekun,Chen, Heshan,Zhou, Jiafen,Wang, Zhongfu,Zhang, Jianbo
supporting information, p. 347 - 352 (2017/02/10)
A magnetic core-shell solid-acid catalyst Fe3O4@C-SO3H was studied for synthesis of O-2,3-unsaturated glycosides through Ferrier rearrangement. The donors include 3,4,6-tri-O-acetyl-D-glucal and 3,4-di-O-acetyl-L-rhamnal. The acceptors consist of primary alcohols, secondary alcohols, tert-butanol, unsaturated alcohols, halogenated alcohol, sterol, sugars, and phenols. O-2,3-Unsaturated glycosides were obtained rapidly (5:1 to 19:1). Moreover, the catalyst can be easily separated from the reaction with an external magnetic force and reused for a minimum of five times without any significant decrease in the yields of the products after every recycle, suggesting it a promising green catalyst in 2,3-unsaturated glycosides syntheses.
