Journal of Sulfur Chemistry 37
1
=
H NMR (400 MHz, CD3OD) δ 7.15–7.43 (m, 15H), 4.86 and 4.56 (ABq, 2H, J 12.6 Hz), 4.80
=
=
=
(d, 1H, J 5.2 Hz), 4.57 and 4.51 (ABq, 2H, J 11.6 Hz), 4.49 and 4.41 (ABq, 2H, J 12.0 Hz),
=
=
=
4.34 (dd, 1H, J 4.8, 5.2 Hz), 4.15 (app t, 1H, J 4.8 Hz), 4.08 (ddd, 1H, J 5.2, 6.0, 10.4 Hz),
3.77 (dd, 1H, J 6.4, 10.4 Hz), 3.67 (dd, 1H, J 6.0, 10.4 Hz); 13C NMR (100 MHz, CD3OD) δ
137.9, 137.9, 137.8, 128.1, 127.9, 127.8, 127.5, 127.4, 127.3, 127.2, 89.0, 82.6, 82.5, 82.2, 72.9,
72.8, 71.7, 70.6; NI-FAB-MS m/z 483 M−.
=
=
3.3. (2S,3S,4R,5R)-3,4-Dihydroxy)-5-(hydroxymethyl)tetrahydrofuran-2-sulfonic acid (7)
A mixture of 148 mg (0.305 mmol) of the 1-C-sulfonate 6, 15 mg of 10% Pd/C, and 10 mL
of ethanol was stirred overnight under a hydrogen atmosphere. The reaction mixture was fil-
tered through a pad of Celite, which was washed with ethanol. The filtrate was concentrated
to afford 59 mg (90%) of the product 7 as a white solid: mp 55–60◦C; [α]D –7.0◦(c 0.33, 1:1
1
=
=
ethanol/methanol); H NMR (400 MHz, CD3OD) δ 4.72 (d, 1H, J 4.8 Hz), 4.26 (dd, 1H, J 3.6,
=
=
=
4.4 Hz), 4.11 (app t, 1H, J 4.0 Hz), 3.91 (ddd, 1H, J 4.4, 6.0, 8.4 Hz), 3.77 (dd, 1H, J 6.4,
12.0 Hz), 3.71 (dd, 1H, J 4.4, 12.0 Hz); 13C NMR (100 MHz, CD3OD) δ 89.1, 86.4, 77.1, 76.2,
=
62.1; NI-FAB-MS m/z 213 M−.
Acknowledgements
We are grateful to the NIH (AI055760) for financial support. H-1 and C-13 NMR spectra of compounds 5, 6, and 7 are
available in the Supplementary Material.
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