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In our case, the alcohol
was prepared by the addition of vinylmagnesium chloride to (tert-butyldimethylsilyloxy)acetaldehyde,
which in turn was prepared by ozonolysis of the bis-TBS ether of cis-but-2-ene-1,4-diol.
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13 Data for the trans-isomer
of tetrahydropyran 2: [α]D
²5 +90.6 (c 0.28, CH2Cl2).
IR (neat): 3054, 2952, 2926, 2855, 1714, 1434, 1315, 1200, 1177,
1098, 898 cm-¹. ¹H
NMR (300 MHz, CDCl3): δ = 0.99 (3 H,
d, J = 6.9
Hz), 1.20-1.32 (2 H, m), 1.47 (1 H, d, J = 3.0
Hz), 1.75-1.91 (2 H, m), 1.99 (1 H, ddd, J = 12.5,
4.3, 2.6 Hz), 2.44 (1 H, dd, J = 14.5,
4.4 Hz), 2.65 (1 H, dd, J = 14.5,
11.0 Hz), 3.48-3.62 (3 H, m), 3.66 (3 H, s), 3.85-3.89
(1 H, m), 4.43 (1 H, ddd, J = 10.8,
5.1, 4.9 Hz), 4.48 (1 H, d, J = 11.8
Hz), 4.54 (1 H, d, J = 11.8 Hz),
7.26-7.36 (5 H, m). ¹³C NMR
(75 MHz, CDCl3): δ = 172.0, 138.5,
128.4, 127.7, 127.5, 73.9, 73.1, 69.7, 66.9, 66.7, 51.7, 41.0, 40.4,
36.0, 33.4, 13.1. MS (EI): m/z = 345 (M + Na), 323
(M + H), 214. HRMS (EI): m/z calcd for C18H27O5 (M + H):
323.1858; found: 323.1859.
17 The enantiomer was prepared by White
et al. (ref. 5b).