35752-46-6Relevant academic research and scientific papers
The mckenna reaction – avoiding side reactions in phosphonate deprotection
Justyna, Katarzyna,Ma?olepsza, Joanna,Kusy, Damian,Maniukiewicz, Waldemar,B?a?ewska, Katarzyna M.
, p. 1436 - 1446 (2020/07/08)
The McKenna reaction is a well-known and popular method for the efficient and mild synthesis of organophosphorus acids. Bromotrimethylsilane (BTMS) is the main reagent in this reaction, which transforms dialkyl phosphonate esters into bis(trimethylsilyl)esters, which are then easily converted into the target acids. However, the versatile character of the McKenna reaction is not always used to its full extent, due to formation of side products. Herein, demonstrated by using model examples we have not only analyzed the typical side processes accompanying the McKenna reaction, but also uncovered new ones. Further, we discovered that some commonly recommended precautions did not always circumvent the side reactions. The proposed results and recommendations may facilitate the synthesis of phosphonic acids.
Dealkylation of dialkyl phosphonates with boron tribromide
Gauvry,Mortier
, p. 553 - 554 (2007/10/03)
Boron tribromide cleanly and quantitatively converts dimethyl-, diethyl-, diisopropyl-, and ditertiobutyl phosphonates RP(O)(OR')2 into the corresponding phosphonic acids RP(O)(OH)2 via methanolysis. The use of boron tribromide is compatible with a variety of functionalities in the R group.
Dealkylation of phosphonate esters with chlorotrimethylsilane
Gutierrez,Prisbe,Rohloff
, p. 1299 - 1302 (2007/10/03)
Chlorotrimethylsilane completely dealkylates phosphonate esters at elevated temperature in a sealed reaction vessel. These conditions are tolerated by a variety of functional groups and lead to high conversions of dimethyl, diethyl and diisopropyl phosphonates to their corresponding phosphonic acids.
Intramolecular cyclopropanation reactions en route to novel P- heterocycles
Hanson, Paul R.,Sprott, Kevin T.,Wrobleski, Aaron D.
, p. 1455 - 1458 (2007/10/03)
The first examples of intramolecular cyclopropanation reactions on a phosphonate template catalyzed by Rh2(OAc)4 are described. These reactions proceed in excellent yield and give mixtures of the P-heterocycles cis-2a-d and trans-2a-d with moderate levels of diastereoselectivity. The diastereoselectivity of this transformation is dependent upon the size of the alkyl group R contained in the alkyl α-diazodiallylphosphonoacetate starting materials 1a-d.
ORGANOPHOSPHORUS COMPOUNDS AS ANTIVIRAL AGENTS
Hutchinson, D. W.,Cload, P. A.,Haugh, M. C.
, p. 285 - 294 (2007/10/02)
The 5'-triphosphates of 2'-5' linked oligoadenylic acids are formed in cells which have been exposed to interferon and may be involved in the antiviral activity of the latter.The lead(II) ion-catalysed oligomerisation of adenosin 5'-phosphorimidazolidate is a convenient route for the preparation of the 5'-phosphates of 2'-5' linked oligoadenylic acids.The latter can readily be converted to the triphosphates or coupled to the 5'-phosphate of nicotinamide nucleoside to give naturally occurring pyrophosphates which may act as reservoirs for the oligoadenylic acids in cells.Pyrophosphate analoques, eg. phophonoacetic and phosphonoformic acids or carbon-substituted methylenebisphosphonic acids are antiviral agents of potential commercial interest as they inhibit the replication of a number of viruses including herpes and influenza.These pyrophosphate analogues do not appear to inhibit virus replication by being incorporated into nucleoside triphosphates which block nucleic acid synthesis.Rather analogues appear to act by forming stable complexes with an essential metal ion (probably zinc) at the active sites of nucleic acid polymerases of viruses.
Treatment of herpes simplex infections
-
, (2008/06/13)
A method of treating herpes simplex infections in warm-blooded animals by administering to said animals a carboxylic ester of phosphonoacetic acid of the formula STR1 wherein R is a C1 -C2 alkyl.
