94283-95-1Relevant academic research and scientific papers
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
Synthesis of Selectively Labeled D-Fructose and D-Fructose Phosphate Analogues Locked in the Cyclic Furanose Form
Persky, Rachel,Albeck, Amnon
, p. 5632 - 5638 (2007/10/03)
2,5-Anhydroglucitol and 2,5-anhydromannitol and their 6-phosphate and 1,6-diphosphate derivatives are cyclic analogues of the α and β anomers of D-fructofuranose, D-fructofuranose-6-phosphate, and D-fructofuranose-1,6-diphosphate. They were synthesized from protected D-mannose or D-glucose. The synthetic method was developed with emphasis on selective 2H labeling of these compounds, as a model for 3H incorporation, which will be used for further biochemical studies. A key cyclization step, based on a benzyl ether nucleophilic attack on an activated alcohol, constructed the ring system. The stereochemistry at C2 (α/β anomers) and at C5 (D sugar) was controlled by selective epimerizations. Mono- and diphosphate analogues were obtained from the same intermediate by changing the sequence of deprotection and phosphorylation steps.
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
