反应详情

To a solution of (R)-benzyl 3-((2S,3R,4S)-2-benzyl-4-hydroxy-3-(triisopropylsilyloxy)pentyloxy)-2-(tert-butoxycarbonylamino)propanoate (410 mg, 0.637 mmol, 1.00 equiv) in EtOAc (13.4 mL, 0.05 M) was added 5% Pd/C (71 mg, 0.033 mmol, 0.05 equiv). The vessel was capped with a septum and the atmosphere replaced with 1 atmosphere (atm) H2 via a needle-equipped balloon. This suspension was stirred for 7 h, filtered through a plug of Celite®, and the plug was washed with EtOAc. Solvent removal provided (R)-3-((2S,3R,4S)-2-benzyl-4-hydroxy-3-(triisopropylsilyloxy)pentyloxy)-2-(tert-butoxycarbonylamino)propanoic acid (352 mg, 100%) as a hard, white foam: IR (neat film) 2944, 2867, 1706, 1163, 1092, 1063, 907, 731 cm−1; 1H NMR (400 MHz, CDCl3) δ 7.26 (s, 2H), 7.21-7.10 (m, 3H), 5.44 (d, J=7.7 Hz, 1H), 4.45 (s, 1H), 3.88 (t, J=6.2 Hz, 1H), 3.78 (dd, J=5.8, 2.5 Hz, 2H), 3.70-3.51 (m, 2H), 3.33 (dd, J=9.3, 5.7 Hz, 1H), 2.90 (dd, J=13.6, 5.2 Hz, 1H), 2.67 (dd, J=13.7, 10.5 Hz, 1H), 2.05 (s, 1H), 1.45 (s, 9H), 1.28 (d, J=6.3 Hz, 3H), 1.04 (s, 21H); 13C NMR (101 MHz, CDCl3) δ 173.08, 155.56, 140.78, 129.08, 128.37, 125.96, 80.25, 71.20, 71.03, 69.08, 53.81, 46.81, 35.18, 28.30, 19.57, 18.20, 12.88; HRMS-ESI (m/z) [M+Na]+ calc'd for C29H51NO7SiNa, 576.3327. found, 576.3341.

1. customThe vessel was capped with a septum
2. filtrationfiltered through a plug of Celite®
3. washthe plug was washed with EtOAc
4. customSolvent removal