1401995-59-2Relevant articles and documents
Selective phosphorylation of diols with a Lewis acid catalyst
Coppola, Kyle A.,Testa, Joseph W.,Allen, Emily E.,Sculimbrene, Bianca R.
, p. 4203 - 4206 (2014)
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.
Catalytic Lewis acid phosphorylation with pyrophosphates
Fenton, Owen S.,Allen, Emily E.,Pedretty, Kyle P.,Till, Sean D.,Todaro, Joseph E.,Sculimbrene, Bianca R.
, p. 9023 - 9028 (2012/11/06)
We report a method for the Lewis acid catalyzed phosphorylation of alcohols with pyrophosphates. Ti(OtBu)4 was found to be the most effective catalyst in the phosphorylation of both primary and secondary alcohols with tetrabenzylpyrophosphate, providing conversions between 54% and >98% and isolated yields between 50% and 97%. Other pyrophosphates with orthogonal protecting groups were synthesized and screened to validate the generality of the approach. This study will describe how benzyl, methyl, ethyl, allyl, and o-nitrobenzyl pyrophosphates are all effective phosphorylating agents under Lewis acid catalysis.