L. Wu, Z. Yin / Carbohydrate Research 365 (2013) 14–19
19
functionalized nano
c-Al2O3 (50 mg). The mixture was stirred at
50 °C for 40 min. After completion of the reaction (TLC), the mix-
ture was put into diethyl ether (50 mL) and microporous filtration
(microporous membrane: PVDF, pore sizes: 0.1 lm). The solvents
were removed under reduced pressure and the crude product
was passed through a short pad of silica to give pure acetylated
product 2c. The catalyst was washed with absolute EtOH, dried
and re-used for a consecutive run under the same reaction
conditions.
1.5. Spectral data of some selected compounds
Figure 5. Reusability of sulfonic acid functionalized nano c-Al2O3 synthesis of 2a.
Compound 2n: 1H NMR (400 Hz, CDCl3) d: 10.10 (br s, 1H), 737
(s, 1H), 5.52 (d, J = 1.9 Hz, 1H), 5.04 (dd, J = 1.9, 6.5 Hz, 1H), 4.76
(dd, J = 3.8, 6.5 Hz, 1H), 4.36 (ddd, J = 3.8, 3.9, 7.2 Hz, 1H), 4.30
(ABX, J = 3.9, 11.6 Hz 1H), 4.23 (ABX, J = 7.2, 11.6 Hz, 1H), 2.27 (s,
3H), 1.96 (s, 3H), 1.52 (s, 3H), 1.32 (s, 3H); MS (ESI): m/z 341
[M+H]+; Anal. Calcd for C15H20N2O7: C 52.94, H 5.92, N 8.23. Found:
C 52.86, H 5.99, N 8.37.
1. Experimental
1.1. Materials and instrumentation
c-Alumina powder with particle size at about 20 nm was
Compound 2; 1H NMR (400 Hz, CDCl3) d: 5.84 (d, J = 3.7 Hz, 1H),
5.19 (d, J = 2.9 Hz, 1H), 4.27 (d, J = 3.7 Hz, 1H), 4.12 (ddd, J = 2.9, 6.3,
7.8 Hz, 1H), 3.80 (ABX, J = 7.8, 10.16 Hz, 1H), 3.62 (ABX, J = 6.2,
10.10 Hz, 1H), 2.00 (s, 3H,), 1.53 (s, 3H), 1.32 (s, 3H), 0.88 (s, 9H),
0.02 (s, 6H); MS (ESI): m/z 347 [M+H]+; Anal. Calcd for C16H30O6Si:
C 55.46, H 8.73. Found: C 55.62, H 8.65.
purchased from aladdin (Shanghai, China) and was used without
further purification. Other reagents and starting materials were
purchased from commercial resources and were used as received.
All products were characterized by comparison of their spectral
and physical data with those previously reported. Progress of the
reactions was monitored by TLC; XRD patterns were recorded using
a Cu Ka radiation source on a Bruker D8 Advance Bruker powder
diffractometer. SEM studies were conducted on a JSM-6390LV.
TEM studies were performed using a JEM 2100 transmission elec-
tron microscope on an accelerating voltage of 150 kV. TGA curves
are recorded using a DT-40 thermoanalyzer. pH analysis was
conducted on a JENCO6171 pH meter. IR spectra were determined
on FTS-40 infrared spectrometer, the samples were in the form of
wafers prepared from a mixture of 1 mg of the product in a
300 mg of KBr. 1H NMR spectra were determined on Bruker AV-
400 spectrometer at room temperature using tetramethylsilane
(TMS) as an internal standard (CDCl3 solution), coupling constants
(J) were measured in Hz. Mass spectra were recorded on a Finnigan
LCQ Advantage mass spectrometer. Elemental analysis was per-
formed by a Vario-III elemental analyzer. Melting points were
determined on a XT-4 binocular microscope and were uncorrected.
Acknowledgment
We are pleased to acknowledge the financial support from
Xinxiang Medical University.
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To a stirred suspension of
dride (5.1 mmol) at room temperature was added sulfonic acid
D-glucose (1 mmol) in acetic anhy-