H. Sun et al. / Tetrahedron Letters 42 (2001) 2451–2453
2453
We expect that analogs of 3a/3b will exhibit more
potent and selective inhibition on sialyltransferases, and
may be extended to other glycosyltransferases.
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Acknowledgements
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We wish to thank the University of Florida and
National Science Foundation (CAREER Award MCB-
9501866 to B.A.H.) for this work.
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9. No attempt was made to determine the stereochemistry
of the hydroxyl group relative to the cyclopropane ring,
but it was assumed that the borane attack occurred from
the less hindered side and no change in configuration
took place during the peroxide oxidation.
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1
12. Selected data for 9: H NMR (300 MHz, CD3Cl) l 6.75
(m, 1H), 3.71 (s, 3H), 3.53 (m, 1H), 3.36 (m, 1H), 2.76
(m, 1H), 2.45 (m, 1H), 2.20 (m, 1H), 1.89 (m, 1H), 1.48
(m, 1H), 1.38 (bs, 1H); 13C NMR (75 MHz, CD3Cl) l
164.87, 141.61, 135.68, 56.31, 51.39, 31.14, 28.88, 24.10,
21.38; HRMS calcd for C9H13O3 (M++H): 169.0865;
1
found: 169.090. For 3a/3b: H NMR (300 MHz, D2O) l
7.75 (d, J=7.62 Hz, 1H), 6.29 (bs, 1H), 5.88 (d, J=7.62
Hz, 1H), 5.75 (m, 1H), 4.45 (m, 3H), 3.93 (m, 1H), 3.83
(m, 1H), 3.58 (m, 1H), 3.44 (m, 1H), 2.45 (m, 1H),
2.20–2.18 (m, 2H), 1.69 (m, 1H), 1.28 (m, 1H); 13C NMR
(75 MHz, D2O) l 181.87, 173.91, 166.47, 158.12, 142.10,
141.61, 137.61, 96.82, 89.63, 89.52, 83.01, 74.46, 69.70,
64.46, 61.68, 31.96, 28.83, 23.65, 21.01; HRMS calcd for
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