98392-78-0Relevant academic research and scientific papers
Synthesis of 2,3-unsaturated glycosides via metal-free Ferrier reaction
De, Kavita,Legros, Julien,Crousse, Benoit,Bonnet-Delpon, Danièle
, p. 10497 - 10500 (2008)
Hexafluoroisopropanol (HFIP) is explored as an effective medium for the synthesis of 2,3-unsaturated glycosides through allylic rearrangement of 3,4,6-tri-O-acetyl glucal. This metal-free, exclusively solvent-promoted Ferrier glycosylation, affords products in good to excellent yields and with good α-selectivity.
Mild and highly efficient stereoselective synthesis of 2,3-unsaturated glycopyranosides using La(NO3)3·6H2O as a catalyst: Ferrier rearrangement
Suryakiran,Reddy, S. Malla,Srinivasulu,Venkateswarlu
, p. 170 - 176 (2008/03/17)
A mild and highly efficient stereoselective reaction of 3,4,6-tri-O-acetyl-d-glucal with a variety of nucleophiles, viz. alcohols, phenols, thiols, thiophenols, and allyl trimethyl silane (TMS), in the presence of 5 mol% of lanthanum(III) nitrate hexahydrate under solvent-free conditions yielded the corresponding 2,3-unsaturated glycopyranosides (pseudoglycals) in excellent yields. Copyright Taylor & Francis Group, LLC.
A facile Er(OTf)3-catalyzed synthesis of 2,3-unsaturated O- and S-glycosides
Procopio, Antonio,Dalpozzo, Renato,De Nino, Antonio,Maiuolo, Loredana,Nardi, Monica,Oliverio, Manuela,Russo, Beatrice
, p. 2125 - 2131 (2008/02/10)
Er(OTf)3 is a useful catalyst for the Ferrier rearrangement furnishing high yields of O- and S-glycosides. The transformation has wide applicability, cleaner reaction profiles, mild reaction conditions, and high stereoselectivity and the catalyst, which is also commercially available, can be recovered and reused.
An Efficient Method for the Synthesis of 2,3-Unsaturated Glycopyranosides Catalyzed by Bismuth Trichloride in Ferrier Rearrangement
Swamy, N. Raghavendra,Venkateswarlu, Y.
, p. 598 - 600 (2007/10/03)
The reaction of tri-O-acetyl-D-glucal and tri-O-benzyl-D-glucal with various alcohols and thiols to afford the corresponding glycopyranosides in excellent yields by bismuth trichloride in acetonitrile at ambient temperature has been demonstrated.
Dy(OTf)3-immobilized in ionic liquids: A novel and recyclable reaction media for the synthesis of 2,3-unsaturated glycopyranosides
Yadav, Jhillu S.,Reddy, Basi V. Subba,Reddy, J. Shyam Sunder
, p. 2390 - 2394 (2007/10/03)
D-Glycals react smoothly with a variety of alcohols, phenols and hydroxy α-amino acids in the presence of 5 mol% dysprosium triflate immobilized in 1-butyl-3-methylimidazolium hexafluorophosphate under mild reaction conditions to afford the corresponding 2,3-unsaturated glycopyranosides in excellent yields with high α-selectivity. The catalyst immobilized in ionic liquids was recycled in subsequent reactions without any apparent loss of activity.
Microwave induced ferrier rearrangement
Sowmya,Balasubramanian
, p. 2097 - 2101 (2007/10/02)
A short and facile entry to the 2, 3-unsaturated O-arylglyco sides via microwave induced Ferrier rearrangement of acetylated glucal is reported.
