801289-08-7Relevant academic research and scientific papers
Synthesis of α- and β-glycosyl isothiocyanates via oxazoline intermediates
Blanco, Jose L. Jimenez,Sylla, Balla,Mellet, Carmen Ortiz,Fernandez, Jose M. Garcia
, p. 4547 - 4550 (2008/02/05)
(Chemical Equation Presented) A practical synthesis of acylated glycosyl isothiocyanates from sugar oxazolines, by reaction with thiophosgene, is reported. In the absence of any additive, the reaction is governed by the reverse anomeric effect, leading to
Synthesis of Sugar Oxazolines by Intramolecular Ritter-Like Reaction of D-Fructose Precursors
Blanco, Jose L. Jimenez,Rubio, Enrique M.,Mellet, Carmen Ortiz,Fernandez, Jose M. Garcia
, p. 2230 - 2232 (2007/10/03)
Treatment of D-fructopyranose and D-fructofuranose 1,2-O-acetonide derivatives with triflic acid in the presence of a variety of nitriles results in the formation of fused or spiro 2-oxazolines. The reaction implies (i) activation of the anomeric centre with simultaneous isopropylidene cleavage, (ii) nucleophilic addition of the nitrile to the corresponding oxocarbenium cation intermediate and (iii) subsequent trapping of the resulting nitrilium ion species by the remaining hydroxyl group in an Ritter-like reaction.
Isothiocyanato derivatives of sugars in the stereoselective synthesis of spironucleosides and spiro-C-glycosides
Gasch, Consolacion,Pradera,Salameh, Bader A.B.,Molina, Jose L.,Fuentes, Jose
, p. 1267 - 1277 (2007/10/03)
A stereocontrolled synthesis of pyranoid and furanoid spironucleosides and spiro-C-glycosides (D-ribo and D-arabino configurations) of oxazolidines, oxazolines and perhydrooxazines via isothiocyanato sugar derivatives is reported. The intermediate isothio
