123417-01-6Relevant articles and documents
Selective phosphorylation on primary alcohols of unprotected polyols
Ladame, Sylvain,Claustre, Samantha,Willson, Michele
, p. 37 - 47 (2001)
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.
Direct mono-phosphorylation of 1,3-diols. A synthesis of FTY720-phosphate
Takeda, Shuzo,Chino, Masao,Kiuchi, Masatoshi,Adachi, Kunitomo
, p. 5169 - 5172 (2005)
A novel method for selective and direct phosphorylation of various 1,3-diols using silver(I) oxide, tetrabenzyl pyrophosphate (TBPP), and tetrahexylammonium iodide affording mono-phosphates was developed. We applied the present method to the synthesis of
Selective phosphorylation of diols with a Lewis acid catalyst
Coppola, Kyle A.,Testa, Joseph W.,Allen, Emily E.,Sculimbrene, Bianca R.
supporting information, p. 4203 - 4206 (2015/02/02)
We report a method for the Lewis acid catalyzed phosphorylation of diols with pyrophosphates. Titanium alkoxides were found to be effective catalysts in the selective mono-phosphorylation for a range of diols. Diols of varying chain lengths and substituents were screened, to study the factors that influence mono- versus di-phosphorylation. It was discovered that 2-alkyl-2-amino-1,3-propanediols can be selectively mono-phosphorylated in up to 97% isolated yield. This structural core is mono-phosphorylated in numerous immunomodulating compounds including the FDA-approved drug, FTY720.
Selective phosphorylation of diols with a Lewis acid catalyst
Coppola, Kyle A.,Testa, Joseph W.,Allen, Emily E.,Sculimbrene, Bianca R.
supporting information, p. 4203 - 4206 (2014/07/22)
We report a method for the Lewis acid catalyzed phosphorylation of diols with pyrophosphates. Titanium alkoxides were found to be effective catalysts in the selective mono-phosphorylation for a range of diols. Diols of varying chain lengths and substituents were screened, to study the factors that influence mono- versus di-phosphorylation. It was discovered that 2-alkyl-2-amino-1,3- propanediols can be selectively mono-phosphorylated in up to 97% isolated yield. This structural core is mono-phosphorylated in numerous immunomodulating compounds including the FDA-approved drug, FTY720.
DIBENZYL PHOSPHORFLUORIDATE, A NEW PHOSPHORYLATING AGENT
Watanabe, Yutaka,Hyodo, Nobuyuki,Ozaki, Shoichiro
, p. 5763 - 5764 (2007/10/02)
The first synthesis of dibenzyl phosphorofluoridate and its utility as a phosphorylating agent are described.