Selective synthesis of phosphate monoesters by dehydrative condensation of phosphoric acid and alcohols promoted by nucleophilic bases.
Phosphate monoesters are synthesized from a mixture of phosphoric acid (1 or 2 equiv) and alcohols (1 equiv) in the presence of tributylamine. The reaction is promoted by nucleophilic bases such as N-alkylimidazole and 4-(N,N-dialkylamino)pyridine. 2',3'-O-Isopropylidene ribonucleosides are selectively converted to their 5'-monophosphates without the protection of amino groups in nucleobases.
Sakakura
Akira
A
Graduate School of Engineering, Nagoya University, Chikusa, Japan.
Katsukawa
Mikimoto
M
Ishihara
Kazuaki
K
D000438:Alcohols / Q000737:chemistry*; D007093:Imidazoles / Q000737:chemistry; D015394:Molecular Structure; D010710:Phosphates / Q000138:chemical synthesis* / Q000737:chemistry*; D010756:Phosphoric Acids / Q000737:chemistry*; D011725:Pyridines / Q000737:chemistry; D012263:Ribonucleosides / Q000737:chemistry*
D000438:Alcohols; D007093:Imidazoles; D010710:Phosphates; D010756:Phosphoric Acids; D011725:Pyridines; D012263:Ribonucleosides; C030242:phosphoric acid