Development of efficient processes for multi-gram scale and divergent preparation of fluorous-Fmoc reagents

作者：Sugiyama Yuya; Endo Natsuki; Ishihara Kazuki; Kobayashi Yuki; Hamamoto Hiromi; Shioiri Takayuki; Matsugi Masato^*

来源：Tetrahedron, 2015, 71(30): 4958-4966.

DOI：10.1016/j.tet.2015.05.083

• Fluorous Fmoc reagent
• Protecting groups
• Large scale synthesis
• Combinatorial chemistry
• Peptides

An optimized, multi-gram scale synthesis of fluorous-Fmoc reagents is described. Fmoc reagents bearing C3F7, C4F9, and C6F13 chains were prepared on multi-gram scale (ca. 1.0-7.0 g) in eight steps with overall yields of 73%, 60%, and 90%, respectively. The order of addition of the fluorous alkenes in a one-pot double tagging Heck reaction was also investigated in order to conduct an encoded mixture synthesis of f-Fmoc reagents. The target f-Fmoc reagents bearing C3F7, C4F9, and C6F13 chains could be effectively separated based on the fluorine content of the molecules.

• 出版日期2015-7-29