Diethylaminosulfur trifluoride
Diethylaminosulfur trifluoride structure
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Common Name | Diethylaminosulfur trifluoride | ||
|---|---|---|---|---|
| CAS Number | 38078-09-0 | Molecular Weight | 161.189 | |
| Density | 1.1±0.1 g/cm3 | Boiling Point | 163.7±9.0 °C at 760 mmHg | |
| Molecular Formula | C4H10F3NS | Melting Point | N/A | |
| MSDS | Chinese USA | Flash Point | 23.9±0.0 °C | |
| Symbol |
GHS02, GHS05, GHS07 |
Signal Word | Danger | |
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Rearrangement of homoallylic alcohols induced by DAST.
Org. Lett. 8 , 2091, (2006) [reaction: see text] Treatment of beta,gamma-unsaturated monoprotected 1,2-diols with diethylaminosulfur trifluoride (DAST) allows the stereoselective formation of beta,gamma-unsaturated aldehydes in good yields and with a good transfer of chirality. |
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Fluorinative Beckmann fragmentation: fluorinative alpha-cleavage of cyclic ketoximes by diethylaminosulfur trifluoride.
Chem. Pharm. Bull. 48(2) , 220-2, (2000) Diethylaminosulfur trifluoride reacted with cyclic ketoximes bearing substituent(s) that can stabilize a carbocation to cause fluorinative fragmentation, affording fluorinated carbonitrile. Ketoximes lacking such substituents afforded complex mixtures. Howeve... |
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Synthesis of functionalized oxazolines and oxazoles with DAST and Deoxo-Fluor.
Org. Lett. 2(8) , 1165-8, (2000) [formula: see text] A mild and highly efficient cyclization of beta-hydroxy amides to oxazolines is described using DAST and Deoxo-Fluor reagents. A one-pot protocol for the synthesis of oxazoles from beta-hydroxy amides is also presented. |
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Ring expansion of cyclic β-amino alcohols induced by diethylaminosulfur trifluoride: synthesis of cyclic amines with a tertiary fluorine at C3.
J. Org. Chem. 77(14) , 6087-99, (2012) As the replacement of a hydrogen atom by a fluorine atom in a compound can have an important impact on its biological properties, the development of methods allowing the introduction of a fluorine atom is of great importance. The scope and limitations of the ... |
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Solid-phase chemical synthesis and in vitro biological evaluation of novel 2β-piperazino-(20R)-5α-pregnane-3α,20-diol N-derivatives as anti-leukemic agents.
Steroids 77(13) , 1403-18, (2012) The steroid nucleus is an interesting scaffold for the development of new therapeutic agents. Within the goal of identifying anticancer agents, new pregnane derivatives were prepared by using a sequence of liquid and solid-phase reactions. After we dehydrated... |
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Stereo- and regio-selectivity of diethylaminosulfur trifluoride as a fluorinating reagent for methyl glycosides.
Carbohydr. Res. 121 , 51-60, (1983) Methyl glycopyranosides reacted with diethylaminosulfur trifluoride (DAST) in the absence of solvent to yield methyl dideoxy-difluoro and deoxy-fluoro glycopyranosides. Methyl alpha-D-glycopyranosides produced 6-deoxy-6-fluoro- and 4,6-dideoxy-4,6-difluoro de... |
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DAST-mediated regioselective anomeric group migration in saccharides.
J. Org. Chem. 74(11) , 4041-8, (2009) When saccharides bearing a sulfur, selenium, or oxygen substituent at the anomeric center and an unprotected hydroxyl group either at C-4 or C-6 were subjected to fluorination with DAST in dichloromethane, a regioselective migration of the anomeric substituen... |
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Synthesis of meiosis-activating sterols containing fluorine.
Acta Chem. Scand. 52(4) , 503-7, (1998) It is documented that specific types of sterol play a major role in the resumption of meiosis in oocytes from mice in vitro. 4,4-Dimethyl-5 alpha-cholesta-8,14,24-trien-3 beta-ol (FF-MAS) isolated from human follicular fluid and 4,4-dimethyl-5 alpha-cholesta-... |
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Fluorination of triptolide and its analogues and their cytotoxicity.
Bioorg. Med. Chem. Lett. 18(7) , 2459-63, (2008) The reaction of triptolide and its analogues with a fluorinating agent, that is, bis(2-methoxyethyl)aminosulfur trifluoride (Deoxo-Fluor) or (diethylamino)sulfur trifluoride (DAST), was studied. One of the fluorinated products, 14beta-dehydroxy-14beta-fluoro ... |
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Syntheses of methyl (4,6-dideoxy-alpha-L-lyxo-hexopyranosyl)-(1-->3)- and (4-deoxy-4-fluoro-alpha-L-rhamnopyranosyl)-(1-->3)- 2-acetamido-2-deoxy-alpha-D-glucopyranosides, analogs of the mycobacterial arabinogalactan linkage disaccharide.
Carbohydr. Res. 322(1-2) , 14-25, (1999) We have made thioglycoside donors for the 4,6-dideoxy-L-lyxo-hexopyranosyl ('4-deoxy-L-rhamnosyl') and 4-deoxy-4-fluoro-L-rhamnosyl monosaccharide residues. The preparation of the deoxyfluororhamnose was not straightforward, and revealed some unexpected behav... |