反应详情

To a solution of tert-butyl ((3S,7S,8R,9S)-7-benzyl-9-methyl-8-((3-methylbut-3-en-1-yl)oxy)-2-oxo-1,5-dioxonan-3-yl)carbamate (100 mg, 0.223 mmol, 1.00 equiv) in EtOAc (3 mL) was added 10% Pd/C (12 mg, 0.011 mmol, 0.05 equiv). The resulting suspension was stirred under an atmosphere of H2 (balloon pressure) for 16 h and filtered through a plug of Celite®. The filtrate was concentrated to provide tert-butyl ((3S,7S,8R,9S)-7-benzyl-8-(isopentyloxy)-9-methyl-2-oxo-1,5-dioxonan-3-yl)carbamate (97 mg, 97%) as a sticky oil: 1H NMR (400 MHz, CDCl3) δ 7.38-7.23 (m, 2H), 7.23-7.11 (m, 3H), 5.13 (d, J=7.7 Hz, 1H), 4.94 (dq, J=9.2, 6.4 Hz, 1H), 4.59 (q, J=7.3 Hz, 1H), 3.88 (dd, J=11.5, 7.3 Hz, 1H), 3.77-3.63 (m, 1H), 3.56 (dt, J=8.7, 6.9 Hz, 1H), 3.49-3.41 (m, 1H), 3.37 (dd, J=10.5, 6.4 Hz, 1H), 3.26 (dd, J=11.3, 7.3 Hz, 1H), 3.20-3.04 (m, 2H), 2.30 (t, J=12.6 Hz, 1H), 1.90 (s, 1H), 1.73 (dp, J=13.3, 6.7 Hz, 1H), 1.55-1.46 (m, 5H), 1.42 (s, 9H), 0.91 (dd, J=6.6, 0.8 Hz, 6H); 13C NMR (101 MHz, CDCl3) δ 172.25, 154.97, 139.96, 129.15, 128.43, 126.11, 85.13, 80.07, 75.58, 72.90, 72.45, 71.19, 52.97, 47.31, 39.17, 35.16, 28.27, 24.90, 22.70, 22.68, 18.77; ESIMS m/z 472.7 ([M+Na]+).

1. filtrationfiltered through a plug of Celite®
2. concentrationThe filtrate was concentrated