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mmol) Yield of 64d (1.35 g, 92%).
1 H NMR (300 MHz, CDCl3): δ 7.36-7.27 (m, 5H), 5.50 (quin, J = 6.8 Hz, 1H), 5.33 (bs, 1H),
5.12 (s, 2H), 4.41 (sep, J = 7.3 Hz, 1H), 1.52-1.41 (m, 6H), 0.18 (s, 4.5H), 0.17 (s, 4.5H); 13 C
NMR (75 MHz, CDCl3): δ 171.8, 155.6, 136.3, 128.6, 128.2, 103.0, 102.8, 90.5, 90.2, 67.0, 62.0,
49.7, 21.4, 18.9, 18.6, -0.2; IR (thin film): ν 3341, 2960, 2178, 1727, 1251 cm -1 ; MS m/z (%) 348
(5), 270 (10), 178 (13), 134 (26), 91 (100); EI-HRMS calcd for C18H25NO4Si m/z [M] + 347.1553;
found 347.1541.
Cbz
TMS
N
H
64e
2-Benzyloxycarbonylaminopropionic acid 1-isopropyl-3-trimethylsilylprop-2-ynyl ester
(64e). Prepared by following general procedure C using: 4-methyl-1-trimethylsilylpent-1-yn-3-ol
(800 mg, 4.71 mmol), DMAP (63 mg, 0.52 mmol), DCC (1.06 g, 5.15 mmol), N-Cbz-alanine
(1.15 g, 5.17 mmol). Yield of 64e (1.65 g, 85%).
1 H NMR (300 MHz, CDCl3): δ 7.37-7.27 (m, 5H), 5.44 (m, 1H), 5.29 (d, J = 5.6 Hz, 0.5H), 5.25
(d, J = 5.7 Hz, 0.5H), 5.12 (s, 2H), 4.49-4.38 (m, 1H), 2.05-1.94 (m, 1H), 1.44 (d, J = 7.1 Hz,
1H), 1.03-0.98 (m, 3H), 0.18 (s, 4.5H), 0.17 (s, 4.5H); 13 C NMR (75 MHz, CDCl3): δ 171.9,
171.7, 155.5, 136.3, 128.4, 128.1, 128.0, 100.8, 100.6, 91.6, 91.4, 70.4, 70.3, 66.8, 49.8, 49.5,
32.4, 32.3, 18.8, 18.3, 18.0, 18.0, 17.4; IR (thin film): ν 3340, 2965, 2180, 1728, 1526 cm -1 ; MS
m/z (%) 376 (6), 375 (14), 295 (25), 280 (34), 223 (50), 91 (100); EI-HRMS calcd for
C20H29NO4Si m/z [M] + 375.1866; found 375.1863.
O
156
O