Fluoride ion promoted deprotection and transesterification in nucleotide triesters
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Fluoride ion promoted deprotection and transesterification in nucleotide triesters.
Tetrabutylammonium fluoride will remove phenyl, trichloroethyl and cyanoethyl groups from nucleotides. In addition to the desired nucleotide products other results including chain cleavage, phosphofluoridates and cyanoethylated thymidine units may be obtained depending on the conditions used. Fluoride ion has been used to successfully exchange phenyl and trichloroethyl groups for methyl, ethyl ...
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Diaryliodonium salts are shown to undergo rapid, fluoride-promoted aryl exchange reactions at room temperature in acetonitrile. Aryl exchange is shown to be exquisitely sensitive to the concentration of fluoride ion in solution; fast exchange is observed as the fluoride concentration approaches a stoichiometric amount at 50 mM substrate concentration. The reaction is slowed, but not halted if b...
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Lewis acid-catalyzed reaction of allyl and benzyl trichloroacetimidates with r-silyl alcohols was found to be a general method for the synthesis of r-alkoxysilanes. Upon exposure to CsF, these r-alkoxysilanes could be made to undergo [2,3]-Wittig rearrangement with an efficiency similar to that realized by the analogous but inherently more toxic r-alkoxystannanes. For over 20 years Wittig rearr...
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Uridine-3'-phosphorothiolate triesters bearing lipophilic moieties were prepared via Michaelis-Arbuzov chemistry. Subsequent deprotection of the S-cholesteryl phosphorothiolate triester afforded the corresponding diester which underwent spontaneous Cyclization to cleanly afford uridine 2',3'-cyclic phosphate. This transesterification reaction could be expedited by treatment with iodine under mi...
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ژورنال
عنوان ژورنال: Nucleic Acids Research
سال: 1979
ISSN: 0305-1048,1362-4962
DOI: 10.1093/nar/7.3.805