113019-34-4Relevant academic research and scientific papers
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.
ZnBr2-catalyzed and microwave-assisted synthesis of 2,3-unsaturated glucosides of hindered phenols and alcohols
Bound, D. James,Bettadaiah,Srinivas
, p. 2565 - 2576 (2014/08/05)
GRAPHICAL ABSTRACT Zinc bromide (ZnBr2) under microwave irradiation efficiently catalyzed the Ferrier reaction of hindered phenols and alcohols to afford the corresponding α-2,3-unsaturated glucoside acetates in good yields and with good stereoselectivity. The reaction affords a facile access to new 2,3-dideoxyglucosides of important phenolic and alcoholic constituents of spices.
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.
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.
Kinetically controlled Ferrier rearrangement of 3-O-mesyl-d-glycal derivatives
Watanabe, Yuhya,Itoh, Tsubasa,Sakakibara, Tohru
scheme or table, p. 516 - 520 (2009/05/11)
The Ferrier rearrangement, which is widely used in carbohydrate chemistry, is generally performed under acidic conditions to give an α anomer with high stereoselectivity. We have found that 3-O-mesyl-d-glycals 2-4 were smoothly reacted with alcohols in th
A convenient synthesis of pseudoglycosides via a Ferrier-type rearrangement using metal-free H3PO4 catalyst
Gorityala, Bala Kishan,Cai, Shuting,Lorpitthaya, Rujee,Ma, Jimei,Pasunooti, Kalyan Kumar,Liu, Xue-Wei
experimental part, p. 676 - 679 (2011/03/19)
A mild and efficient synthesis of pseudoglycals has been developed using a metal-free catalytic system. Phosphoric acid proved to be an excellent catalyst for conversion of 2,4,6-tri-O-acetyl-d-glycal to 2,3-unsaturated O-glycosides. A wide range of alcoh
Microwave-induced, Montmorillonite K10-catalyzed Ferrier rearrangement of tri-O-acetyl-D-galactal: Mild, eco-friendly, rapid glycosidation with allylic rearrangement
Shanmugasundaram, Bhagavathy,Bose, Ajay K.,Balasubramanian, Kalpattu K.
, p. 6795 - 6798 (2007/10/03)
Montmorillonite K10 was found to catalyze, under microwave irradiation, rapid O-glycosidation of 3,4,6-tri-O-acetyl-D-galactal to afford exclusively the alkyl and aryl 2,3-dideoxy-D-threo-hex-2-enopyranosides with very high α-selectivity and without the formation of the 2-deoxy-D-lyxo-hexopyranosides. Under these conditions, 3,4,6-tri-O-acetyl-D-glucal as usual also underwent the Ferrier rearrangement.
Highly stereoselective synthesis of pseudoglycals via Yb(OTf)3 catalyzed Ferrier glycosylation
Takhi,Abdel-Rahman,Schmidt
, p. 427 - 429 (2007/10/03)
The reaction of tri-O-acetyl-D-glucal with various alcohols and thiols was effectively promoted by a catalytic amount of Yb(OTf)3 to produce a variety of pseudoglycals via Ferrier rearrangement in excellent yields and anomeric selectivity.
Novel optically active 1,3-aminoalcohols derived from D-glucal
Iovel,Oehme,Michalik,Lukevics
, p. 40 - 46 (2007/10/03)
A series of ethyl(phenyl) 6-amino-2,3,6-trideoxy-α-D-glucopyranosides (amino = piperidino (Pip), pyrrolidino (Pyr), azetidino (Az), Bu2N) have been prepared from tri-O-acetyl-D-glucal to obtain catalysts for asymmetric synthesis and the starting compounds for the syntheses of other bidentate ligands.
Synthesis of 4-(4,6-di-O-benzyl-2,3-dideoxy-β-D-erythro-hex-2- enopyranosyl)pyrazoles from 3,4,6-tri-O-acetyl-D-glucal
Borrachero-Moya, Pastora,Cabrera-Escribano, Francisca,Gomez-Guillen, Manuel,Del Rocio Paredes-Leon, Maria
, p. 181 - 190 (2007/10/03)
3-(4,6-Di-O-benzyl-2,3-dideoxy-b-D-erythro-hex-2-enopyranosyl)-2,4- pentanedione and its analogue 2-(4,6-di-O-benzyl-2,3-dideoxy-β-D-erythro- hex-2-enopyranosyl)-1-phenyl-1,3-butanedione, prepared from 3,4,6-tri-O- acetyl-1,5-anhydro-2-deoxy-D-arabino-hex
