Verhoeven, Jonas; De Vleeschouwer, Freija; Kong, Hanchu; Van Hecke, Kristof; Pande, Vineet; Sun, Weimei; Vos, Ann; Wu, Tongfei; Meerpoel, Lieven; Thuring, Jan Willem; Verniest, Guido published an article in 2019, the title of the article was Preparation of 4′-Spirocyclobutyl Nucleoside Analogues as Novel and Versatile Adenosine Scaffolds.Safety of (3aS,4S,6R,6aR)-4-(Iodomethyl)-6-methoxy-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxole And the article contains the following content:
Despite the large variety of modified nucleosides that have been reported, the preparation of constrained 4′-spirocyclic adenosine analogs has received very little attention. We discovered that the [2+2]-cycloaddition of dichloroketene on readily available 4′-exo-methylene furanose sugars efficiently results in the diastereoselective formation of novel 4′-spirocyclobutanones. The reaction mechanism was investigated via d. functional theory (DFT) and found to proceed either via a non-synchronous or stepwise reaction sequence, controlled by the stereochem. at the 3′-position of the sugar substrate. The obtained dichlorocyclobutanones were converted into nucleoside analogs, providing access to a novel class of chiral 4′-spirocyclobutyl adenosine mimetics in eight steps from com. available sugars. Assessment of the biol. activity of designed 4′-spirocyclic adenosine analogs identified potent inhibitors for protein methyltransferase target PRMT5. The experimental process involved the reaction of (3aS,4S,6R,6aR)-4-(Iodomethyl)-6-methoxy-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxole(cas: 38838-06-1).Safety of (3aS,4S,6R,6aR)-4-(Iodomethyl)-6-methoxy-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxole
The Article related to crystal structure spirocyclobutyl nucleoside preparation spirocyclic adenosine methyltransferase, gibbs free energy spirocyclobutyl nucleoside preparation adenosine dft cycloaddition, sam-mimetics, cycloaddition, cyclobutanones, enol ethers, spiro compounds and other aspects.Safety of (3aS,4S,6R,6aR)-4-(Iodomethyl)-6-methoxy-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxole
Referemce:
1,3-Benzodioxole – Wikipedia,
Dioxole | C3H4O2 – PubChem