An article Catalytic Chemoselective O-Phosphorylation of Alcohols WOS:000517832800024 published article about ASYMMETRIC PHOSPHORYLATION; SELECTIVE PHOSPHORYLATION; OLIGONUCLEOTIDE SYNTHESIS; PHOSPHORIC-ACID; FUNCTIONALIZATION; PHOSPHOPEPTIDES; PENTAPHOSPHATES; CONDENSATION; EXPLORATION; CONVERSION in [Domon, K.; Fujiyoshi, K.; Kawashima, S. A.; Yamatsugu, K.; Kanai, M.] Univ Tokyo, Grad Sch Pharmaceut Sci, Tokyo 1130033, Japan; [Puripat, M.; Hatanaka, M.] Nara Inst Sci & Technol NAIST, Inst Res Initiatives, Div Res Strategy, Ikoma 6300192, Japan; [Hatanaka, M.] NAIST, Grad Sch Sci & Technol, Data Sci Ctr, Ikoma 6300192, Japan in 2020, Cited 41. SDS of cas: 93-97-0. The Name is Benzoic anhydride. Through research, I have a further understanding and discovery of 93-97-0
Phosphorylation of alcohols is a fundamentally important reaction in both life science and physical science. Product phosphate monoesters play key roles in living organisms, natural products, pharmaceuticals, and organic materials. Most of the chemical methods to date for synthesizing phosphate monoesters, however, require multistep sequences or are limited to specific types of substrates possibly due to harsh conditions. An alternative way to enable the simple production of phosphate monoesters from highly functionalized precursor alcohols is, thus, highly desired. We report herein a catalytic phosphorylation of alcohols with high functional group tolerance using tetrabutylammonium hydrogen sulfate (TBAHS) and phosphoenolpyruvic acid monopotassium salt (PEP-K) as the catalyst and phosphoryl donor, respectively. This method enables the direct introduction of a nonprotected phosphate group to the hydroxy group of a diverse menu of alcohol substrates, including functionalized small molecules, carbohydrates, and unprotected peptides. Nuclear magnetic resonance, mass spectrometric, and density functional theory analyses suggest that an unprecedented mixed anhydride species, generated from PEP-K and TBAHS, acts as an active phosphoryl donor in this reaction. This operationally simple and chemoselective catalytic phosphorylation allows for the efficient production of densely functionalized O-phosphorylated compounds, which are useful in diverse fields including biology and medicine.
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