998
G. Cousins et al. / Carbohydrate Research 338 (2003) 995–998
1.8. 1
inositol (3e)
D
-3-O-Benzoyl-1,2:5,6-di-O-isopropylidene-chiro-
2859, 1749 cm−1; HRMS: Calcd for C20H31O7, m/z
383.2070 [M+H]; Found, m/z 383.2064.
Eluted with 5:1 hexanes–EtOAc (Rf 0.25) to give a
white solid mp 81 °C [h]2D1 +47.4° (c 1.4×10−2
,
Acknowledgements
1
CH2Cl2); H NMR (300 MHz CDCl3): l 1.36 (s, 3 H,
CMe2), 1.38 (s, 3 H, CMe2), 1.54 (s, 6 H, CMe2), 3.6
(dd, 1 H, J 8.1, 11.5 Hz, H-4), 4.31 (dd, 1 H, J 6.1, 8.1
Hz, H-5), 4.4 (dd, 1 H, J 5.7, 8.1 Hz, H-2) 4.5 (m, 2 H,
H-1, H-6), 5.24 (dd, 1 H, J 8.1, 11.5 Hz, H-3) 7.45 (m,
2 H, Bz) 7.55(m, 1 H, Bz) 8.08 (m, 2 H, Bz); 13C NMR
(75 MHz CDCl3): l 25.7, 25.9, 27.9, 28.1, 72.1, 74.2,
75.6, 75.9, 76.7, 79.3, 109.8, 109.9, 128.6, 130.2, 133.6,
166.7; IR (neat) 3465, 2987, 1723 cm−1; HRMS: Calcd
for C19H25O7, m/z 365.1558 [M+H]; Found, m/z
365.1595. Anal. Calcd for C19H24O7: C, 62.63; H, 6.64.
Found: C, 62.80; H, 6.61.
We thank New Zealand Pharmaceuticals for a gener-
ous gift of pinitol and G.C. acknowledges Industrial
Research Limited for her graduate scholarship.
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Eluted with 5:1 hexanes–EtOAc (Rf 0.15) to give a
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,
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chiro-inositol (4a)
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1
colourless oil, [h]2D1 +25.9° (c 9.7×10−3, CH2Cl2); H
NMR (300 MHz CDCl3): l 1.39–1.68 (m, 20 H, Cy),
3.61 (dd, 1 H, J 8.3, 11.2 Hz, H-4), 4.14 (s, 2 H,
CH2Cl), 4.24 (m, 2 H, H-2, H-5), 4.53 (m, 2 H, H-1,
H-6), 4.99 (dd, 1 H, J 8.5, 11.5 Hz, H-3) 6.07 (brs, 1 H,
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75.4, 75.4, 78.3, 110.2, 110.4, 167.2; IR (neat) 3437,
2937, 1732 cm−1; HRMS: Calcd for C20H3035ClO7, m/z
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D
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Eluted with 5:1 hexanes–EtOAc (Rf 0.16) to give a
colourless oil, [h]2D1 +27.0° (c 1.49×10−2, CH2Cl2); 1H
NMR (300 MHz CDCl3): l 1.36–1.56 (m, 20 H, Cy),
2.14 (s, 3 H, Ac), 2.62 (brs, 1 H, OH), 3.54 (dd, 1 H, J
8.3, 11.2 Hz, H-3), 4.20 (m, 2 H, H-2, H-5), 4.49 (m, 2
H, H-1, H-6), 4.91 (dd, 1 H, J 8.5, 11.5 Hz, H-3); 13C
NMR (75 MHz CDCl3): l 21.3, 23.8, 23.9, 24.1, 24.2,
25.1, 25.2, 34.9, 35.1, 37.6, 38.0, 72.1, 73.8, 75.0, 75.3,
76.0, 78.8, 110.2, 110.3, 171.2; IR (neat) 3466, 2934,
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