37699-02-8Relevant academic research and scientific papers
Synthesis of novel C4-linked C2-imidazole ribonucleoside phosphoramidite and its application to probing the catalytic mechanism of a ribozyme
Araki, Lisa,Morita, Keiji,Yamaguchi, Maho,Zhao, Zheng-Yun,Wilson, Timothy J.,Lilley, David M. J.,Harusawa, Shinya
supporting information; experimental part, p. 2350 - 2356 (2009/07/25)
The synthesis of a novel C4-linked C2-imidazole ribonucleoside phosphoramidite (ICN-C2-PA 1) with a two-carbon linker between imidazole and ribose moieties is described. In the phosphoramidite, POM and 2-cyanoethyl groups were select
Rearrangements in the course of fluorination by diethylaminosulfur trifluoride at C-2 of glycopyranosides: Some new parameters
Dax, Karl,Albert, Martin,Hammond, David,Illaszewicz, Carina,Purkarthofer, Thomas,Tscherner, Martin,Weber, Hansjoerg
, p. 427 - 448 (2007/10/03)
Reaction of a series of 21 glycosides unprotected at O-2 and featuring various configurations with DAST (diethylaminosulfur trifluoride) was monitored by 19F NMR spectroscopy. By means of the diacritical set of data (shift values and coupling c
Selectivity in the SmI2-induced deoxygenation of thiazolylketoses for formyl C-glycoside synthesis and revised structure of C-ribofuranosides
Dondoni, Alessandro,Formaglio, Paolo,Marra, Alberto,Massi, Alessandro
, p. 7719 - 7727 (2007/10/03)
Deoxygenation of thiazolylketose acetates using SmI2-(CH2OH)2 or TMSOTf-Et3SiH affords thiazolyl C-glycosides with opposite α/β ratios. Examination of the thiazolyl α- and β-C-ribofuranoside pair by NOE experime
Chemistry of glucal halohydrins(II): An unusual protecting group effect in the competitive formation of formyl furanosides and methyl glycosides
Kozlowski, John S.,Marzabadi, Cecilia H.,Rath, Nigam P.,Spilling, Christopher D.
, p. 301 - 313 (2007/10/03)
A remarkable protecting group influence was observed in the base-induced reaction of protected halohydrins derived from D-glycals. Tri-O-methyl and tri-O-benzyl halohydrins react with cesium carbonate in methanol at room temperature to give methyl glycosides as the major product and unsaturated formyl furanosides as the minor product. Whereas, the tri-O-tert-butyldimethylsilyl (t-BuMe2Si)-protected halohydrins reacted with cesium carbonate in methanol at room temperature to give a mixture of epimeric formyl furanosides, and at reflux to give an unsaturated formyl furanoside, as the only products. The tri-O-methyl and tri-O-benzyl halohydrins react slowly at elevated temperature to give predominantly furans. In comparison, the tri-O-t-BuMe2Si halohydrins reacted completely after five minutes to give a mixture of epimeric formyl furanosides. The tri-O-t-BuMe2Si iodohydrins were oxidized to the corresponding iodolactones, which also underwent a based-induced ring contraction in methanol to give the furanose 1-methylcarboxylate esters.
Asymmetric Cyclopropanation of Allylic Ethers: Cleavage and Regeneration of the Chiral Auxiliary
Charette, Andre B.,Cote, Bernard
, p. 933 - 936 (2007/10/02)
The ring contraction reaction of 2-O-oxy>-β-D-glucopyranosides and their corresponding α-anomers is reported.The rearrangement was shown to occur under extremely mild basic conditions to allow isolation of acid-sensitive optica
