Development of efficient processes for multi-gram scale and divergent preparation of fluorous-Fmoc reagents. Issue 30 (29th July 2015)

• Record Type: Journal Article
• Authors: Sugiyama, Yuya; Endo, Natsuki; Ishihara, Kazuki; Kobayashi, Yuki; Hamamoto, Hiromi; Shioiri, Takayuki; Matsugi, Masato
• Is Part Of: Tetrahedron. Volume 71:Issue 30(2015)
• Page Start: 4958
• Page End: 4966
• Publication Date: 2015-07-29
• Subjects: Fluorous Fmoc reagent -- Protecting groups -- Large scale synthesis -- Combinatorial chemistry -- Peptides; Chemistry, Organic -- Periodicals; 547.005
• DOI: 10.1016/j.tet.2015.05.083
• Languages: English
• ISSNs: 0040-4020

Abstract

Abstract: An optimized, multi-gram scale synthesis of fluorous-Fmoc reagents is described. Fmoc reagents bearing C3 F7, C4 F9, and C6 F13 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 C3 F7, C4 F9, and C6 F13 chains could be effectively separated based on the fluorine content of the molecules. Graphical abstract: