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Spectroscopic data for selected compounds.
Compound 3: [α]
d
²8 +20.1
(c 0.53, CHCl3) {Lit.² +19.0
(c 0.77, CHCl3)}. ¹H
NMR (500 MHz, CDCl3): δ = 1.80 (dd, J = 6.6 Hz,
3 H), 1.94-2.37 (m, 2 H), 2.45-2.69
(m, 2 H), 4.46 (dd, J = 6.8, 12.8 Hz,
1 H), 4.57 (dd, J = 5.8,
8.8 Hz, 1 H), 5.30 (t, J = 10.0 Hz,
1 H), 5.85 (qd, J = 6.9,
13.9 Hz, 1 H), 6.19 (t, J = 11.0 Hz,
1 H), 6.28-6.42 (m, 1 H). ¹³C
NMR (75 MHz, CDCl3): δ = 18.4,
23.7, 28.4, 70.1, 82.8, 123.9, 126.0, 133.8, 133.9, 177.0. IR (neat):
3383, 2924, 2854, 1767, 1460, 1184, 1039 cm-¹.
MS (LC-MS): m/z = 205 [M + Na]+.
HRMS:
m/z calcd for C10H14NaO3:
205.0849; found: 205.0840. Compound 7: [α]
d
²5 +18.7
(c 1.2, CHCl3). ¹H
NMR (300 MHz, CDCl3): δ = 1.54-1.84
(m, 4 H), 2.39 (d, J = 2.2 Hz,
1 H), 3.33 (s, 3 H), 3.46-3.60 (m, 5 H),
4.10-4.27 (m, 2 H), 4.56 (s, 2 H), 4.71
(Abq, J = 7.2 Hz,
2 H).
¹³C NMR (75 MHz,
CDCl3): δ = 25.8, 28.5, 55.1, 56.0,
65.1, 67.3, 74.1, 81.7, 84.6, 96.3, 97.8. IR (neat): 3418, 3279, 2937,
2150, 1646, 1447, 1381, 1150, 1106, 1037, 917 cm-¹. MS
(LC-MS): m/z = 255 [M + Na]+.
HRMS: m/z calcd
for C11H20NaO5: 255.1208; found:
255.1203. Compound 11: [α]
d
²5 +8.0
(c 1.0, CHCl3). ¹H
NMR (200 MHz, CDCl3): δ = 0.10
(s, 6 H), 0.91 (s, 9 H), 1.35 (s, 3 H),
1.37 (s, 3 H), 2.14-2.23 (m, 1 H), 2.40-2.49
(m, 1 H), 2.90 (br s, 1 H, OH), 3.59-3.70
(m, 3 H), 3.81-3.90 (m, 2 H), 5.07-5.16
(m, 2 H), 5.82-5.96 (m, 1 H). ¹³C
NMR (75 MHz, CDCl3): δ = -5.5, 18.3,
25.8, 26.8, 26.9, 37.8, 64.2, 71.5, 79.5, 81.6, 108.8, 117.5, 134.5.
IR (neat): 3447, 2932, 1617, 1379, 1254, 1082, 837, 774 cm-¹.
MS (LC-MS): m/z = 339 [M + Na]+.
HRMS: m/z calcd
for C16H32SiNaO4: 339.1967; found:
339.1970
