- Site-specific functionalisation of proteins by a Staudinger-type reaction using unsymmetrical phosphites
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Unsymmetrical phosphites react efficiently in a Staudinger reaction with p-azido-phenylalanine, which can be applied for the biotinylation of proteins, thereby expanding the scope of the chemoselective Staudinger-phosphite reaction of aryl azides with symmetrical phosphites to the corresponding phosphoramidates. The Royal Society of Chemistry 2010.
- Boehrsch, Verena,Serwa, Remigiusz,Majkut, Paul,Krause, Eberhard,Hackenberger, Christian P. R.
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scheme or table
p. 3176 - 3178
(2010/09/04)
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- DIARYL ALKYLPHOSPHONATES AND METHODS FOR PREPARING SAME
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A method for preparing substantially pure optionally substituted diaryl alkylphosphonates from an optionally substituted triarylphosphite and an optionally substituted trialkylphosphite or an optionally substituted alkanol under special reaction conditions is described.
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Page/Page column 25-26
(2010/11/28)
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- DIARYL ALKYLPHOSPHONATES AND METHODS FOR PREPARING SAME
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A method of making optionally substituted diaryl alkylphosphonates from an optionally substituted arylol, an optionally substituted alkanol, and a phosphorous trihalide is described.
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Page/Page column 6-7
(2008/06/13)
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- Bisphosphonate prodrugs. Synthesis and identification of (1-hydroxyethylidene)-1,1-bisphosphonic acid tetraesters by mass spectrometry, NMR spectroscopy and x-ray crystallography
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The preparation and identification of symmetric, H3CC(OH)[P(O)(OR)2]2, where R=Me, Et, Pr1, Ph, and non-symmetric, H3CC(OH)[P(O)(OR1)(OR2)][P(O)(OR3)(O R4)], where R1=Me, R2=R3=R4=Ph; R1=R2=R3=Ph, R4=Me; R1=R3=Me, R2=R4=Ph; R1=R2=Et, Pr1, Ph and R3=R4=Me: tetraester derivatives of etidronate have been studied. Compounds were prepared from HP(O)(OR1)(OR2) and AcP(O)(OR3)(OR4) species under reflux. Mechanism studies have been made using HP(O)(OCD3)(OPh) and AcP(O)(OMe)(OPh) as starting materials. 1H, 13C, 31P NMR data and the MS fragmentation data in the gas phase are reported. The solid-state structures are given for three of the compounds, where R=Et, Ph and R1=R2=Ph, R3=R4=Me.
- Turhanen, Petri A.,Ahlgren, Markku J.,Jaervinen, Tomi,Vepsaelaeinen, Jouko J.
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p. 115 - 133
(2007/10/03)
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- Phosphitylation via the Mitsunobu reaction
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Treatment of a dialkyl phosphite with triphenylphosphine and diisopropyl azodicarboxylate in toluene, followed by addition of an alcohol, results in the formation of the corresponding trialkyl phosphite. Similarly, dialkyl phosphonites can be synthesised from monoalkyl phosphites (alkyl phosphinates).
- Grice, I. Darren,Harvey, Peta J.,Jenkins, Ian D.,Gallagher, Michael J.,Ranasinghe, Millagahamada G.
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p. 1087 - 1090
(2007/10/03)
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- Successive Displacements of Phenoxy by Methoxy Groups in Triphenyl Phosphite Ozonide: Mechanism of the Accelerated Singlet Oxygen Formation with Pyridine and Methanol
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The ozonides from triphenyl phosphite, methyl diphenyl phosphite, and phenyl dimethyl phosphite form a series (1-3) which liberate singlet thermally at rates incresing by an order of magnitude for each substitution of methoxy for phenoxy.Trimethyl phosphite ozonide (4) fits in this series, although the very low temperature limit of its stability has not been determined.When triphenyl phosphite ozonide (1) is treated with methanol and pyridine in methylene chloride and yields singlet oxygen at an accelerated rate, the phenyl methyl phosphates 6 and 7 and trimethyl phosphate (8) are produced in a total amount corresponding to the singlet oxygen evolved.The lower the temperature, the greater the predominance of trimethyl phosphate (8) in the product.Each of the mixed phosphite ozonides 2 and 3 is in turn subject to accelerated singlet oxygen formation by the action of methanol and pyridine; in each case the phosphates formed contain at least one more methoxy group than the starting ozonide.These facts establish the mechanism of the accelerated singlet oxygen liberation as a successive displacement of phenoxy by methoxy groups on the initial phosphite ozonide, each newly formed aliphatic-aromatic phosphite ozonide decomposing thermally at its own increased rate.
- Bartlett, Paul D.,Lonzetta, Charles M.
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p. 1984 - 1988
(2007/10/02)
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