
Tetrahedron p. 4277 - 4290 (1996)
Update date:2022-08-02
Topics:
Chow, Hak-Fun
Chan, Ida Yuk-Kit
Mak, Chi Ching
Ng, Man-Kit
Polyether dendritic sectors 1-4 from the first to the fourth generations, respectively, were prepared by a convergent approach from readily available 4-tert-butylphenol, phloroglucinol and 1,3-dibromopropane. Using a three-step iterative synthetic sequence involving mono-O-alkylation of [Gn]-OH with excess 1,3-dibromopropane, bis-O-alkylation of the resulting compound with 5-benzyloxyresorcinol 5 followed by hydrogenolysis with palladium catalyst, [Gn(n + 1)]-OH of the next higher generation could be prepared in good yields. These dendritic sectors have good solubility properties and are inert in both acidic and basic media, and do not show any redox behaviour from-2.0 to +1.9 V. Hence they are useful dendritic building blocks for the preparation of functional dendrimers.
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