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18
Spectroscopic
Data for Compound 2
[α]D
²5 +3.6
(c 1.0, CHCl3). ¹H
NMR (300 MHz, CDCl3): δ = 5.22
(dq, J = 9.1,
1.1 Hz, 1 H), 4.32 (dd, J = 7.0,
4.1 Hz, 1 H), 2.64 (qd, J = 7.1,
4.1 Hz, 1 H), 2.43-2.50 (m, 1 H), 2.42 (d, J = 1.1 Hz,
3 H), 1.45 (s, 9 H), 1.19 (d, J = 7.1
Hz, 3 H), 1.10 (br s, 18 H), 0.98-1.15 (m, 3 H), 1.01 (d, J = 7.0 Hz,
3
H). ¹³C NMR (75 MHz, CDCl3): δ = 173.0,
137.6, 100.3, 80.2, 75.7, 47.1, 45.3, 33.7, 28.1, 18.3, 16.1, 13.1,
10.9.
IR (film): 1732, 1640, 1257, 883 cm-¹.
MS (DCI/NH3):
m/z = 551 [M + H]+,
472 [M + NH4
t-Bu]+.
19
Spectroscopic
Data for Compound 10
[α]D
²5 +5.5
(c 1.05, CHCl3). ¹H
NMR (300 MHz, CDCl3): δ = 6.23
(d, J = 9.8
Hz, 1 H), 4.28 (dd, J = 6.8,
4.1 Hz, 1 H), 2.52-2.67 (m, 2 H), 1.47 (s, 9 H), 1.13 (d, J = 7.2 Hz,
3 H), 1.10 (s, 18 H), 1.04-1.13 (s, 3 H), 1.07 (d, J = 7.0 Hz,
3 H). ¹³C NMR (75 MHz, CDCl3): δ = 172.7,
140.8, 88.8, 80.7, 75.1, 46.9, 42.0, 28.2, 18.2, 15.5, 13.1, 9.4.
IR (film): 1733, 1460, 1255, 882 cm-¹.
MS (DCI/NH3): m/z = 529 [M + H]+. Anal.
Calcd for C21H40Br2O3Si:
C, 47.73; H, 7.63. Found: C, 47.81; H, 7.51.
20
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23
Spectroscopic
Data for Compound 1
[α]D
²5 -2.5
(c 0.8, CHCl3). ¹H
NMR (300 MHz, CDCl3): δ = 9.85
(dd, J = 2.5,
1.3 Hz, 1 H), 4.91 (ddd, J = 10.5,
7.4, 4.0 Hz, 1 H), 3.87 (t, J = 2.3
Hz, 1 H), 2.80 (td, J = 7.5,
2.3 Hz, 1 H), 2.78 (td, J = 16.7,
4.0, 1.3 Hz, 1 H), 2.68 (ddd, J = 16.7,
7.4, 2.5 Hz, 1 H), 2.04-2.15 (m, 1 H), 1.28 (d, J = 7.5 Hz,
3 H), 0.98-1.10 (m, 24 H). ¹³C
NMR (75 MHz, CDCl3): δ = 199.5,
173.1, 76.3, 75.0, 46.5, 44.4, 33.6, 18.1, 16.7, 13.9, 12.7. IR
(film): 2731, 1735, 1223, 883 cm-¹.
MS
(DCI/NH3): m/z = 360 [M + NH4]+,
343 [M + H]+.