Nimje, Roshan Y.; Vytla, Devaiah; Kuppusamy, Prakasam; Velayuthaperumal, Rajeswari; Jarugu, Lokesh Babu; Reddy, China Anki; Chikkananjaiah, Nanjundaswamy Kanikahalli; Rampulla, Richard A.; Cavallaro, Cullen L.; Li, Jianqing; Mathur, Arvind; Gupta, Anuradha; Roy, Amrita published the artcile< Synthesis of differentially protected azatryptophan analogs via Pd2(dba)3/XPhos catalyzed Negishi coupling of N-Ts azaindole halides with zinc derivative from Fmoc-protected tert-butyl (R)-2-amino-3-iodopropanoate>, Category: pyridine-derivatives, the main research area is azatryptophan protected synthesis; azaindole tosyl halide Negishi coupling aminoiodopropanoate zinc.
Unnatural amino acids play an important role in peptide based drug discovery. Herein, we report a class of differentially protected azatryptophan derivatives synthesized from N-tosyl-3-haloazaindoles (I) (Pg = protective groups: Ts (tosyl), Fmoc (9-fluorenylmethoxycarbonyl), and tert-Bu) and Fmoc-protected tert-Bu iodoalanine (II) (Fmoc = 9-fluorenylmethoxycarbonyl) via a Negishi coupling. Through ligand screening, Pd2(dba)3/XPhos was found to be a superior catalyst for the coupling of 1 with the zinc derivative of 2 to give tert-Bu (S)-2-((((9H-fluoren-9-yl)methoxy)carbonyl)amino)-3-(1-tosyl-1H-pyrrolo[2,3-b]pyridin-3-yl)propanoate derivatives (III) (Pg = protective groups: Ts, Fmoc, and tert-Bu; Fmoc = 9-fluorenylmethoxycarbonyl) in 69-91% isolated yields. In addition, we have demonstrated that the protecting groups, namely, Ts, Fmoc, and tert-Bu, can be easily removed selectively.
Journal of Organic Chemistry published new progress about (Fluorenylmethoxy)carbonyl group. 23612-36-4 belongs to class pyridine-derivatives, and the molecular formula is C7H5BrN2, Category: pyridine-derivatives.