94898-52-9Relevant academic research and scientific papers
Bis(2-methoxyethyl)aminosulfur trifluoride: A new broad-spectrum deoxofluorinating agent with enhanced thermal stability
Lal, Gauri S.,Fez, Guido P.,Pesaresi, Reno J.,Prozonic, Frank M.
, p. 215 - 216 (1999)
Bis(2-methoxyethyl)aminosulfur trifluoride (Deoxo-Fluor) is effective for the conversion of alcohols to alkyl fluorides, aldehydes/ketones to the corresponding gem-difluorides and also for the transformation of carboxylic acids to their trifluoromethyl derivatives; it is a less thermally sensitive, broader-spectrum alternative to the traditional dialkylaminosulfur trifluoride (DAST) deoxofluorination reagents.
Synthesis of glyceryl glycosides related to A-type prymnesin toxins
Hems, Edward S.,Nepogodiev, Sergey A.,Rejzek, Martin,Field, Robert A.
supporting information, p. 14 - 23 (2018/05/03)
A suite of glycosylated glycerol derivatives representing various fragments of the glycosylated ichthyotoxins called prymnesins were chemically synthesised. Glycerol was used to represent a small fragment of the prymnesin backbone, and was glycosylated at
Direct C-glycosylation of organotrifluoroborates with glycosyl fluorides and its application to the total synthesis of (+)-varitriol
Zeng, Jing,Vedachalam, Seenuvasan,Xiang, Shaohua,Liu, Xue-Wei
supporting information; experimental part, p. 42 - 45 (2011/03/22)
A mild, stereoselective, and quick approach to accessing alkynyl and alkenyl C-glycosides via BF3?Et2O promoted coupling of organotrifluoroborates and glycosyl fluorides is reported. The application of this method was further demonstrated by the concise and efficient total synthesis of (+)-varitriol in only seven steps.
Deoxyfluorination of alcohols using N,N-diethyl-α,α-difluoro- (m-methylbenzyl)amine
Kobayashi, Shingo,Yoneda, Atushi,Fukuhara, Tsuyoshi,Hara, Shoji
, p. 6923 - 6930 (2007/10/03)
Deoxyfluorination of alcohols was carried out using N,N-diethyl-α, α-difluoro-(m-methylbenzyl)amine (DFMBA). Primary alcohols were effectively converted to fluorides under microwave irradiation or conventional heating. Deoxyfluorination of an anomeric hydroxy group in sugars by DFMBA proceeded at below room temperature and glycosyl fluorides could be obtained in good yields. The deoxyfluorination reaction chemoselectively proceeded and various protecting groups on the sugar can survive under the reaction conditions.
A CONVENIENT, ONE-STEP, HIGH-YIELD REPLACEMENT OF AN ANOMERIC HYDROXYL GROUP BY A FLUORINE ATOM USING DAST. PREPARATION OF GLYCOSYL FLUORIDES.
Posner, Gary H.,Haines, Stephen R.
, p. 5 - 8 (2007/10/02)
The anomeric hydroxyl group of various furanose and pyranose hemiacetals can be replaced by a fluorine atom stereoselectively, conveniently, mildly, and on gram-scale using DAST in THF at room temperature.
A NEW METHOD FOR THE SYNTHESIS OF GLYCOSYL FLUORIDES
Rosenbrook, Wm.,Riley, D.A.,Lartey, P.A.
, p. 3 - 4 (2007/10/02)
Neat (diethylamino)sulfur trifluoride (DAST) has been found to react with the free anomeric hydroxyl of suitably protected aldoses and ketoses to afford glycosyl fluorides.
THE SYNTHESIS OF GLYCOSYL FLUORIDES USING PYRIDINIUM POLY(HYDROGEN FLUORIDE)
Szarek, Walter A.,Grynkiewicz, Grzegorz,Doboszewski, Bogdan,Hay, George W.
, p. 1751 - 1754 (2007/10/02)
Partially protected monosaccharides, having the anomeric hydroxyl group underivatized, react with poly(hydrogen fluoride) to yield the corresponding glycosyl fluorides.
