Leucine, N-carboxy-, N-benzyl ester, L- → Phenyl-(3R)-3-(N-carbobenzyloxyleucyl)amino-4-phenylbut-1-enyl Sulfone

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Reaction Steps

Cbz-Leu-D-Phe-VS-Ph was prepared from Cbz-Leu-OH and D-Phe-VS-Ph.HCl using standard mixed anhydride coupling method, yield 81%. 1H-NMR (CDCl3) δ 0.8-0.9 (2d, 6H, 2×Leu-CH3), 1.4-1.6 (m, 2H, Leu-CH2), 2.06 (m, 1H, Leu-CH), 2.9-3.0 (m, 2H, CH2-Phe), 3.9-4.0 (m, 1H, α-H), 4.8-4.9 (b, 1H, α-H), 4.9-5.0 (m, 1H, NH), 5.1 (m, 2H, Cbz), 6.3-6.4 (d & b, 2H, NH and CH═), 6.9-7.0 (dd, 1H, CH═), 7.1-7.4 (m, 10H, 2×Ph), 7.5-7.7 (m, 5H, SO2-Ph). MS (ESI) m/z 535.

Provenance & Evidence