1012802-95-7Relevant articles and documents
Practical Synthesis of a Stable Precursor for Positron Emission Tomography Imaging Agent 18F-GTP1
Clagg, Kyle,Gosselin, Francis,Lim, Ngiap-Kie,Nack, William A.,O'Shea, Paul D.,Sirois, Lauren E.,White, Nicholas A.,Zhang, Haiming
, p. 1690 - 1699 (2020)
18F-GTP1 is a deuterated small molecule positron emission tomography (PET) imaging agent used to visualize tau tangles in Alzheimer's disease patients. The first-generation synthesis of 18F-GTP1's nonradiolabeled alkyl tosylate precursor was plagued by low-yielding steps, inefficient chromatographic purifications, and variable product quality. Due to these limitations, a more robust second-generation route was developed and successfully executed on kilogram scale. A reduction with LiAlD4 incorporated geminal deuterium atoms, while an efficient amidation reaction accessed the key acrylamide coupling partner. Moreover, the tricyclic imidazo[1,2-a]pyrimidine core was assembled via a novel, convergent, and highly selective phosphoramidate-directed annulation. The improved synthesis eliminated all chromatography en route to a high-yielding and reproducible acid-promoted tosylation as the final step.
μ-Oxo-Dinuclear-Iron(III)-Catalyzed O-Selective Acylation of Aliphatic and Aromatic Amino Alcohols and Transesterification of Tertiary Alcohols
Horikawa, Rikiya,Fujimoto, Chika,Yazaki, Ryo,Ohshima, Takashi
, p. 12278 - 12281 (2016/08/24)
A highly chemoselective and reactive μ-oxo-dinuclear iron(III) salen catalyst for transesterification was developed. The developed iron complex catalyzed acylation of aliphatic amino alcohols with nearly perfect O-selectivity, even when using activated esters, for which chemoselectivity is more difficult to control. In addition, O-selective transesterification of aromatic amino alcohols was achieved for the first time. The high activity of the iron complex enabled the use of sterically congested tertiary alcohols, including unprecedented tert-butanol.
