160956-79-6Relevant academic research and scientific papers
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
Reinvestigation of Phenolic Ferrier Reaction: Selective Synthesis of Aryl O-Δ2-Glycosides
Noshita, Toshiro,Sugiyama, Takeyoshi,Kitazumi, Yoshiharu,Oritani, Takayuki
, p. 2052 - 2055 (2007/10/02)
Reinvestigation of the phenolic Ferrier reaction is described.Ferrier reaction between acetylglycals and phenols in toluene in the presence of a catalytic amount of lewis acid at low temperature gave aryl O-Δ2-glycosides in moderate to good yie
Phenolic ferrier reaction and its application to the natural product synthesis
Noshita, Toshiro,Sugiyama, Takeyoshi,Kitazumi, Yoshiharu,Oritani, Takayuki
, p. 8259 - 8262 (2007/10/02)
Ferrier reaction between acetylglycals and phenols proceeded smoothly to give α-O-Δ2 glycosides predominantly. The products were converted to bio-active natural products.
