764674-85-3Relevant academic research and scientific papers
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)
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.
Aza-Ferrier rearrangement of glycals with amides promoted by molecular iodine
Begum, Zubeda,Kishore, Ch.,Veerabhadra Reddy,Reddy, B.V. Subba
, p. 6048 - 6050 (2014)
Amidoglycosidation of tri-O-acetyl-d-glucal with different N-nucleophiles such as t-butyl carbamate, N-benzyl carbamate, N-ethyl carbamate, tosyl amide, and mesyl amide has been achieved using an equimolar amount of molecular iodine under mild and neutral
An eco-friendly tandem tosylation/Ferrier N-glycosylation of amines catalyzed by Er(OTf)3 in 2-MeTHF
Nardi, Monica,Cano, Natividad Herrera,De Nino, Antonio,Di Gioia, Maria Luisa,Maiuolo, Loredana,Oliverio, Manuela,Santiago, Ana,Sorrentino, Diletta,Procopio, Antonio
supporting information, p. 1721 - 1726 (2017/04/13)
Er(OTf)3 in 2-MeTHF provides a new and eco-friendly process for Ferrier glycosylation of sulfonamides and amino acids with various N-nucleophiles. The stereoselective synthesis of 2,3-unsaturated-N-pseudoglycals was carried out with 3,4,6-tri-O-acetyl-D-glucal and different nucleophiles affording good results in a short time.
Zn(II) Triflate-Catalyzed N-Glycosylation: Synthesis of Sulfonamide and Amide Functionalized 2,3-Unsaturated Glycosides
Reddy, Thurpu Raghavender,Battina, Suresh Kumar,Kashyap, Sudhir
, p. 133 - 144 (2015/04/27)
(Figure Presented) highly efficient and mild method for the synthesis of glycosyl sulfonamides and glycosyl amides from glycal has been described using Zn(OTf)2 as an economical and environmentally friendly catalyst. Various N-nucleophiles comprising sulf
Ruthenium trichloride catalyzed synthesis of 2,3-unsaturated-N-glycosides via Ferrier azaglycosylation
Reddy, Thurpu Raghavender,Chittela, Sravanthi,Kashyap, Sudhir
supporting information, p. 9224 - 9229 (2017/09/08)
An efficient, economical and mild protocol for the synthesis of 2,3-unsaturated-N-glycosides has been developed using ruthenium(III) chloride. The Ferrier azaglycosylation of glycals with various N-nucleophiles such as sulfonamides, benzamides, carbamates and N-substituted sulfonamides proceeded smoothly to afford the corresponding 2,3-unsaturated-N-glycosides or ‘N-pseudoglycals’ in good yields (64–98%). High α-anomeric selectivity was observed with N-substituted sulfonamides such as N-benzyl or N-phenyl sulfonamides under similar conditions.
A mild and efficient synthetic protocol for Ferrier azaglycosylation promoted by ZnCl2/Al2O3
Ding, Feiqing,William, Ronny,Gorityala, Bala Kishan,Ma, Jimei,Wang, Siming,Liu, Xue-Wei
experimental part, p. 3146 - 3148 (2010/08/07)
An improved method for the Ferrier sulfonamidoglycosylation of tri-O-acetyl-d-glucal with different N-nucleophiles has been developed. ZnCl2 impregnated on activated alumina acts as an excellent reagent system for the conversion of 3,4,6-tri-O-
