26292-51-3Relevant articles and documents
Use of a phosphonate methyltransferase in the identification of the fosfazinomycin biosynthetic gene cluster
Gao, Jiangtao,Ju, Kou-San,Yu, Xiaomin,Velasquez, Juan E.,Mukherjee, Subha,Lee, Jaeheon,Zhao, Changming,Evans, Bradley S.,Doroghazi, James R.,Metcalf, William W.,Van Der Donk, Wilfred A.
supporting information, p. 1334 - 1337 (2014/03/21)
Natural product discovery has been boosted by genome mining approaches, but compound purification is often still challenging. We report an enzymatic strategy for stable isotope labeling of phosphonates in extract (SILPE) that facilitates their purificatio
Selective phosphorylation on primary alcohols of unprotected polyols
Ladame, Sylvain,Claustre, Samantha,Willson, Michele
, p. 37 - 47 (2007/10/03)
The triad tribenzylphosphite-iodine-pyridine offers a general selective method for phosphorylation reactions of primary alcohols of unprotected α-diols and polyols. A mechanistic study by 31P NMR allowed to evidence the formation, from iododibenzyl phosphate and pyridine, of a very reactive pyridinium salt intermediate. This analysis shows that pyridine behaves as a covalent catalyst like DMAP in acylation reactions from acylchloride. Due to its steric hindrance and high reactivity, this species appears to be the efficient selective phosphorylation reagent but leads to dibenzylphosphoric esters. Under mild conditions, the cleavage of benzyl groups gives monoester phosphoric acid.
A NEW, CONVENIENT AND EFFICIENT GENERAL PROCEDURE FOR THE CONVERSION OF ALCOHOLS INTO THEIR DIBENZYL PHOSPHOROTRIESTERS USING N,N-DIETHYL DIBENZYL PHOSPHORAMIDITE
Perich, J. W.,Johns, R. B.
, p. 101 - 102 (2007/10/02)
A general procedure is described for the near-quantitative preparation of alkyl dibenzyl phosphates by treating primary, secondary or tertiary alcohols with N,N-diethyl dibenzyl phosphoramidite/1H,5-methyltetrazole followed by mild oxidation of the resultant alkyl dibenzyl phosphites with 3-chloroperoxybenzoic acid.
