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Ferrier rearrangement
About: Ferrier rearrangement is a research topic. Over the lifetime, 321 publications have been published within this topic receiving 5524 citations.
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TL;DR: A reagent system comprising tetrabutylammonium nitrate-trifluoroacetic anhydride-triethylamine has been developed for the synthesis of 2-nitroglycals from various protected glycals, and some of the products have been converted into 2,3-diamino-2, 3-dideoxyglycosides and methyl N-acetyl-D-lividosaminide.
Abstract: A reagent system comprising tetrabutylammonium nitrate–trifluoroacetic anhydride–triethylamine has been developed for the synthesis of 2-nitroglycals from various protected glycals. The base-catalyzed Ferrier rearrangement on tri-O-acetylated 2-nitroglycals has been reported for the first time. Reactivity of these nitroacetates and associated selectivity has been examined, and some of the products have been converted into 2,3-diamino-2,3-dideoxyglycosides and methyl N-acetyl-d-lividosaminide.
37 citations
TL;DR: F-CeNA modified oligonucleotides were significantly more stable against digestion by snake venom phosphodiesterases (SVPD) as compared to unmodified DNA, 2'-fluoro RNA (FRNA), 2'-methoxyethyl RNA (MOE), and FHNAmodified oligon nucleotides.
Abstract: We report the design and synthesis of 2′-fluoro cyclohexenyl nucleic acid (F-CeNA) pyrimidine phosphoramidites and the synthesis and biophysical, structural, and biological evaluation of modified oligonucleotides. The synthesis of the nucleoside phosphoramidites was accomplished in multigram quantities starting from commercially available methyl-d-mannose pyranoside. Installation of the fluorine atom was accomplished using nonafluorobutanesulfonyl fluoride, and the cyclohexenyl ring system was assembled by means of a palladium-catalyzed Ferrier rearrangement. Installation of the nucleobase was carried out under Mitsunobu conditions followed by standard protecting group manipulations to provide the desired pyrimidine phosphoramidites. Biophysical evaluation indicated that F-CeNA shows behavior similar to that of a 2′-modified nucleotide, and duplexes with RNA showed slightly lower duplex thermostability as compared to that of the more rigid 3′-fluoro hexitol nucleic acid (FHNA). However, F-CeNA modified ol...
36 citations
35 citations
TL;DR: In this paper, the reaction of tri-O-acetyl-D-glucal with nucleophiles to afford the corresponding 2,3-unsaturated glycopyranosides in excellent yields by zirconium(IV) chloride in acetonitrile at ambient temperature has been demonstrated.
35 citations
TL;DR: In this paper, the Ferrier rearrangement of a selection of protected glycals was successfully performed using a commercially available H-USY zeolite CBV-720 as catalyst, selected after screening a range of similar catalysts.
34 citations