3323-72-6Relevant articles and documents
Stereoselective synthesis of D-galactal-derived N-ethoxycarbonyl aziridine, as a new, improved synthetic protocol to glycal-derived N-activated vinyl aziridines
Princiotto, Salvatore,Di Bussolo, Valeria,Bordoni, Vittorio,Favero, Lucilla,Crotti, Stefano,Uccello Barretta, Gloria,Balzano, Federica,Crotti, Paolo
, p. 829 - 837 (2017)
A new protocol for the synthesis of D-galactal-derived N-ethoxycarbonyl vinyl aziridine 1β-CO2Et, starting from tri-O-acetyl-D-glucal, is described. The new protocol constitutes a simple and fast access, with a satisfactory overall yield (5 steps, 36%), to a D-galactal-derived vinyl aziridine with a clear improvement compared with the previously described procedure leading to the structurally related N-nosyl aziridine 1β-Ns which, starting from the same precursor, proceeded through 13 steps with a low, decidedly unsatisfactory, overall yield (3%).
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.
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.
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.
Gd(OTf)3 catalyzed preparation of 2,3-unsaturated O-, S-, N-, and C-pyranosides from glycals by Ferrier Rearrangement
Chen, Peiran,Su, Jie
supporting information, p. 84 - 94 (2015/12/23)
By using Gd(OTf)3 as the catalyst, synthesis of 2,3-unsaturated-glycosides has been performed by Ferrier Rearrangement. A series of 2,3-unsaturated O-, S-, N-, and C-glycosides were obtained from 3,4,6-tri-O-acetyl-d-glucal, 3,4,6-tri-O-benzyl-d-glucal, and 3,4-di-O-acetyl-l-rhamnal under mild reaction conditions in good yields and high anomeric selectivities.
Hafnium(IV) triflate as a highly efficient catalyst for Ferrier rearrangement of O- and S-nucleophiles with glycals
Liu, Yonghui,Song, Tianbang,Meng, Weijia,Xu, Yun,Wang, Peng George,Zhao, Wei
supporting information, p. 2758 - 2762 (2016/06/09)
A highly efficient method to afford 2,3-unsaturated glycosides was described. In the presence of Hafnium(IV) triflate, a variety of 2,3-unsaturated-O- and S-glycosides have been obtained by stereoselective glycosylation of 3,4,6-tri-O-acetyl-d-glucal and hexa-O-acetyl-d-lactal with various acceptors in good isolated yields.
Y(OTf)3 as a highly efficient catalyst in Ferrier Rearrangement for the synthesis of O- and S-2,3-unsaturated glycopyranosides
Chen, Peiran,Li, Shan
supporting information, p. 5813 - 5816 (2015/02/19)
By using Y(OTf)3 as the catalyst, a series of 2,3-unsaturated-glucosides have been synthesized from 3,4,6-tri-O-acetyl-d-glucal, 3,4-di-O-acetyl-l-rhamnal, and 3,4,6-tri-O-benzyl-d-glucal under mild reaction conditions in good yields with high anomeric selectivities. It was found that, in this reaction, 3,4,6-tri-O-benzyl-d-glucal behaved differently from the other two glucals when it was reacted with phenol, O-benzyl glucoside instead of O-phenyl glucoside formed as the sole product. An explanation is given for this phenomenon.
Sm(OTf)3as a highly efficient catalyst for the synthesis of 2,3-unsaturated O- and S-pyranosides from glycals and the temperature-dependent formation of 4-O-acetyl-6-deoxy-2,3-unsaturated S-pyranosides and 4-O-acetyl-6-deoxy-3-alkylthio glycals
Chen, Peiran,Zhang, Dalin
, p. 8505 - 8510 (2014/12/10)
By using Sm(OTf)3as the catalyst, synthesis of 2,3-unsaturated-glycosides has been performed. A series of 2,3-unsaturated glycosides were obtained from 3,4,6-tri-O-acetyl-d-glucal or 3,4-di-O-acetyl-l-rhamnal under mild reaction conditions in g
An efficient procedure for the synthesis of 2,3-unsaturated-O-glycosides: TiCl3(OTf) as the catalyst for type i Ferrier rearrangement
Chen, Peiran,Lin, Lei
, p. 4524 - 4531 (2013/06/27)
An efficient type I Ferrier rearrangement reaction system for the synthesis of 2,3-unsaturated-O-glycosides has been established by using TiCl 3(OTf) as the catalyst. A series of 2,3-unsaturated-O-glucosides were prepared from 3,4,6-tri-O-acetyl-d-glucal in good yield and high anomeric selectivity.
