|别名||二乙氨基三氟化硫 ;二乙胺基三氟化硫, 三氟化二乙氨基硫 ;DAST Sulfur Trifluoride Diethylamine Complex|
|标识符号||GHS02, GHS05, GHS07|
An improved method for the synthesis of protected glycosyl fluorides from thioglycosides using N,N-diethylaminosulfur trifluoride (DAST)
The direct conversion of thioglycosides to glycosyl fluorides frequently used in oligosaccharide synthesis was examined using N,N-diethylaminosulfur trifluoride (DAST). Although the reaction proceeded...Read More
Skeletal rearrangements resulting from reactions of 1,6:2,3- and 1,6:3,4-dianhydro-β-D-hexopyranoses with diethylaminosulphur trifluoride.
A complete series of eight 1,6:2,3- and 1,6:3,4-dianhydro-β-D-hexopyranoses were subjected to fluorination with DAST. The 1,6:3,4-dianhydropyranoses yielded solely products of skeletal rearrangement ...Read More
DAST-mediated cyclization of α,α-disubstituted-α-acylaminoketones: efficient and divergent synthesis of unprecedented heterocycles.
The design of a new potent nonsteroidal ecdysone agonist led to the discovery of a diethylaminosulfur trifluoride (DAST)-mediated cyclization of α,α-disubstituted-α-acylaminoketones. The resulting ...Read More
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 dichloromet...Read More
The DAST-mediated conversion of a range of alcohols to the corresponding fluorides in a microstructured device is described. This safe, practical fluorination method will facilitate reactions currentl...Read More
[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...Read More
Fluorinative Beckmann fragmentation: fluorinative alpha-cleavage of cyclic ketoximes by diethylaminosulfur trifluoride.
Diethylaminosulfur trifluoride reacted with cyclic ketoximes bearing substituent(s) that can stabilize a carbocation to cause fluorinative fragmentation, affording fluorinated carbonitrile. Ketoximes ...Read More
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.
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 deoxyfluor...Read More
Short-chain 3-fluoro-(dihydro)ceramide analogues are synthesized from L-serine using diethylaminosulfur trifluoride (DAST) as fluorinating agent. The apoptogenic activity of these compounds was measur...Read More
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 fro...Read More
Steroidal allylic fluorination using diethylaminosulfur trifluoride: a convenient method for the synthesis of 3 beta-acetoxy-7 alpha- and 7 beta-fluoroandrost-5-en-17-one.
This paper discusses our findings regarding fluorination of the diastereomeric 3 beta-acetoxy-7-hydroxyandrost-5-en-17-ones (3 and 4) at the allylic 7-hydroxyl group using diethylaminosulfur trifluori...Read More
Stereo- and regio-selectivity of diethylaminosulfur trifluoride as a fluorinating reagent for methyl glycosides.
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...Read More
The synthesis and biological activity of kanamycin A derivatives with an omega-amino-alpha-fluoroalkanoyl side chain on the 1-amino group are described. The fluorinated amino acids (4) for the side ch...Read More
Introduction of fluorine into the sugar moiety of nucleoside using diethylaminosulfur trifluoride (DAST).
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.
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 sequen...Read More
Ring expansion of cyclic β-amino alcohols induced by diethylaminosulfur trifluoride: synthesis of cyclic amines with a tertiary fluorine at C3.
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 ato...Read More
Synthesis and anti-HIV-1 activity of 1-substiuted 6-(3-cyanobenzoyl) and [(3-cyanophenyl)fluoromethyl]-5-ethyl-uracils.
1-Substiuted 6-(3-cyanobenzoyl) and [(3-cyanophenyl)fluoromethyl]-5-ethyl-uracils were synthesized and evaluated in cell-based assays against HIV-1 wild-type and its clinically relevant non-nucleoside...Read More
Based on a literature precedent, preparation of methyl 4-azido-3,4,6-trideoxy-3-fluoro-alpha-D-mannopyranoside (18) was attempted via fluorination of methyl 4-azido-2-O-benzyl-4,6-dideoxy-alpha-D-altr...Read More
Pyrimidine nucleosides (or their 5'-aldehydes) when treated with DAST give O2,5'-(fluoro)-anhydronucleosides. If this is prevented by blocking N-3 or O4, the desired 5'-deoxy-5'-(d...Read More