8142
R. Balamurugan, S.R. Koppolu / Tetrahedron 65 (2009) 8139–8142
4. Experimental section
Acknowledgements
4.1. General remarks
The authors thank DST, New Delhi, India for financial support.
The authors extend their thanks to the School of Chemistry, Uni-
versity of Hyderabad for providing necessary start-up grants. K.S.R.
is grateful to CSIR, India for a fellowship.
All reagents were obtained commercially and used without
further purification unless otherwise mentioned. Dichloromethane
was freshly distilled over anhydrous CaH2. Acetonitrile was distilled
over CaH2 and stored under argon atmosphere. Thin-layer chro-
matography was performed by using Merck silica gel F-254 coated
aluminum plates and the visualization of spots was done using UV
illumination and charring the TLC plates sprayed with Seebach so-
lution or 5% H2SO4 solution in methanol. Column chromatography
was performed over silica gel procured from Merck, using hexanes
and ethyl acetate mixture as eluent. Solvents were removed under
reduced pressure using rotovap. The 1H NMR spectra were recorded
in a Bruker Avance 400 MHz NMR machine using solutions in CDCl3
containing TMS as an internal standard. IR spectra were recorded on
JASCO FT/IR-5300 spectrometer. Elemental (C, H, N) analysis were
done using Thermo Finnigan Flash EA 1112 analyzer. Optical rota-
tions were measured using Rudolph Research Analytical Autopol-IV
polarimeter.
Supplementary data
Characterization data and spectra of all the Ferrier products are
provided. Supplementary data associated with this article can be
References and notes
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To a solution of 3,4,6-tri-O-acetyl-
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(1.2 equiv) in anhydrous CH2Cl2 (3 mL/mmol) AuCl3 (0.5–2 mol %)
was added at room temperature. The reaction mixture was stirred
at the same temperature. After complete consumption of the
starting glycal derivative, solvent was evaporated and the residue
was loaded on a silica gel column. The product was purified using
EtOAc/hexanes as eluent system.
4.3. General procedure for the AuCl3-catalyzed one-pot
Ferrier and subsequent glycosylation reactions
To a solution of 3,4,6-tri-O-acetyl-D-glucal 1 (1 equiv) and
propargyl alcohol (1.2 equiv) in dry solvent (5 mL/mmol) AuCl3
(2 mol %) was added. The reaction mixture was stirred at room
temperature. On complete consumption of 1 to form 4e, which
generally takes around 6 h, aglycon (1.2 equiv) was added. The
reaction mixture was stirred under inert atmosphere. After
stirring for specified time given in Table 4 it was purified using
silica gel column using ethyl acetate and hexane mixture as
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