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17. Experimental procedure: PMA/SiO2 catalyst was prepared
following the published procedure.6d Preparation of gly-
cosides: To a solution of tri-O-acetyl glucal (272 mg,
1.0 mmol) and alcohol or allyl trimethylsilane (2.0 mmol)
in acetonitrile was added 1 mol % PMA/SiO2 (0.01 mmol,
based on PMA), and the mixture stirred at r.t. for 10–
15 min. After completion of the reaction as indicated by
TLC, the solvent was removed under reduced pressure and
the residue was dissolved in THF (2 mL) and filtered. The
filtrate was concentrated under reduced pressure and
purified by column chromatography (100–200 silica gel
mesh) using hexane and EtOAc to afford pure glycosides.
The filtered catalyst was reused without drying. Spectral
data for 2a: 1H NMR (CDCl3, 200 MHz) d ppm: 2.08
(s, 6H), 2.35–2.45 (m, 2H), 3.95 (dt, 1H, J = 6.5 and
3.7 Hz), 4.10–4.20 (m, 2H), 4.25–4.30 (m, 1H), 5.05–5.20
(m, 3H), 5.75–5.95 (m, 3H). Compound 2g: 2.08, 2.10
(2 · s, 6H), 2.4 (t, J = 2.2 Hz, 1H), 4.0–4.08 (m, 1H), 4.20–
4.28 (m, 2H), 4.30 (m, 2H), 5.2 (br s, 1H), 5.32–5.36 (dd,
J = 9.6, 1.2 Hz, 1H), 5.8–5.9 (m, 2H). Compound 2m: 2.06
(s, 3H), 2.10 (s, 3H), 4.19–4.22 (m, 2H), 4.34–4.40 (m, 1H),
5.30–5.35 (m, 1H), 5.66–5.68 (m, 1H), 5.83–5.88 (m, 1H),
5.98–6.04 (m, 1H), 7.39–7.42 (m, 4H).
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