69247-18-3Relevant academic research and scientific papers
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)
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.
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.
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.
Glycal approach to the synthesis of macrolide (-)-A26771B
Saidhareddy, Puli,Shaw, Arun K.
, p. 29114 - 29120 (2015/04/22)
A convergent total synthesis of a 16-membered macrolactone natural product (-)-A26771B 1 starting from 3,4,6-tri-O-acetyl-d-glucal 7 is reported. The Ferrier rearrangement of acetylated glucal 7, cross metathesis between chiral fragments 3 and 4, Yamaguchi macrolactonization and selective oxidation of the allylic alcohol are the key features of the synthesis.
"One-pot" access to α-d-mannopyranosides from glycals employing ruthenium catalysis
Chittela, Sravanthi,Reddy, Thurpu Raghavender,Krishna, Palakodety Radha,Kashyap, Sudhir
, p. 46327 - 46331 (2015/02/19)
Ru-catalyzed synthesis of α-d-mannopyranosides from glucal is described via one-pot glycosylation-dihydroxylation reaction. This method is amenable to a variety of acceptors, including carbohydrate-derived and amino-acid containing alcohols to obtain mannosylated peptides and disaccharides.
FeCl3.6H2O/C: An Efficient and Recyclable Catalyst for the Synthesis of 2,3-Unsaturated O-and S-Glycosides
Zhou, Jiafen,Chen, Heshan,Shan, Junjie,Li, Juan,Yang, Guofang,Chen, Xuan,Xin, Kunyun,Zhang, Jianbo,Tang, Jie
, p. 313 - 325 (2015/10/06)
A novel method for synthesizing 2,3-unsaturated glycosides has been developed using a handy and eco-friendly immobilized catalyst, FeCl3.6H2O/C. A series of 2,3-unsaturated O-and S-glycosides were obtained for bioassay from corresponding 3,4,6-tri-O-acetyl-D-glucal and D-galactal in good to excellent yields (56%-99%) and high anomeric selectivity (α/β = 7:1 to >19:1). Furthermore, the catalyst was efficient on gram-scale reactions and recyclable for at least three times.
3,5-Dinitrobenzoic acid catalyzed synthesis of 2,3-unsaturated O- and S-glycosides and tetrahydropyranylation of alcohols and phenols
Bodipati, Naganjaneyulu,Palla, Srinivasa Rao,Komera, Venkateshwarlu,Peddinti, Rama Krishna
supporting information, p. 6878 - 6881 (2015/02/02)
A simple procedure for the synthesis of 2,3-unsaturated glycosides in acetonitrile and tetrahydropyranylation of alcohols and phenols in dichloromethane in the presence of 3,5-dinitrobenzoic acid is described. A variety of alcohols and thiols are reacted with glycals to give the desired products in high yields with high α-selectivity.
Gold(III) Chloride and Phenylacetylene: A Catalyst System for the Ferrier Rearrangement, and O-Glycosylation of 1-O-Acetyl Sugars as Glycosyl Donors
Roy, Rashmi,Rajasekaran, Parasuraman,Mallick, Asadulla,Vankar, Yashwant D.
, p. 5564 - 5573 (2014/10/15)
We have developed a new catalyst system comprising AuCl3 and phenylacetylene that promotes the Ferrier rearrangement of glycals and 2-acetoxymethylglycals with different nucleophiles, and also the O-glycosylation of 1-O-acetyl sugars to obtain a variety of useful glycosides at room temperature through relay catalysis. Good anomeric selectivity was observed for the Ferrier rearrangements, whereas the O-glycosylation of 1-O-acetyl sugars gave mixtures of diastereomers with moderate to excellent selectivity.
Ferrier rearrangement and 2-deoxy sugar synthesis from d-glycals mediated by layered α-zirconium sulfophenylphosphonate-methanphosphonate as heterogeneous catalyst
Rosati, Ornelio,Curini, Massimo,Messina, Federica,Marcotullio, Maria Carla,Cravotto, Giancarlo
, p. 169 - 175 (2013/03/13)
Layered α-zirconium sulfophenylphosphonate-methanphosphonate is a solid acid catalyst that catalyzes Ferrier rearrangement from d-glycals and alcoholic nucleophiles under mild reaction conditions in short time and good yields. Notably, the combination of α-zirconium sulfophenylphosphonate- methanphosphonate and lithium bromide change the regioselectivity of this process affording 2-deoxy sugars in good yields. Graphical Abstract: [Figure not available: see fulltext.]
