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Kinetic products under thermodynamic condititions: Rapid entry into anomeric substituted -D-galactofuranosides using microwave irradiation and selective Lewis
 

Summary: Kinetic products under thermodynamic condititions: Rapid entry into anomeric
substituted -D-galactofuranosides using microwave irradiation and selective Lewis
acids
Soumava Santra, Tarick El-Baba, Emily Jonas, and Peter R. Andreana
Materials and Methods
All Reagents were purchased from Aldrich unless otherwise noted. Anhydrous ferric
chloride was purchased from Alfa Aesar. Anhydrous methanol was purchased from EMD
chemicals (DriSolv). Palladium chloride was purchased from STREM chemicals. Indium
chloride, copper iodide and copper sulfate were purchased from Alfa Aesar. TMSOTf was
purchased from Acros organics. Allyl alcohol was distilled prior to use. Except as otherwise
indicated, reactions were carried out under argon. Microwave reactions were conducted using a
capped vial on a CEM Discover Microwave System. All reactions were monitored by thin layer
chromatography using 0.25 mm Dynamic Adsorbents, L.L.C. precoated silica gel (particle size
0.03-0.07 mm, catalog no. 84111). Column chromatography was performed using Whatman
Purasil 60 (230-400 mesh ASTM) silica gel. Yields refer to chromatographically and
spectroscopically pure compounds, except as otherwise noted. Diastereomeric ratios were
determined from 1
H NMR spectra of non-purified reaction mixtures. Proton and carbon-13 NMR
spectra were recorded on Varian Mercury 400, Varian Unity 500 and Varian 500 Direct Drive
System spectrometers. The residual CDCl3 singlet at 7.26 ppm and 77 ppm were used as

  

Source: Andreana, Peter R. - Department of Chemistry, Wayne State University

 

Collections: Chemistry