Journal
JOURNAL OF CARBOHYDRATE CHEMISTRY
Volume 29, Issue 1, Pages 20-29Publisher
TAYLOR & FRANCIS INC
DOI: 10.1080/07328300903477796
Keywords
Ferrier rearrangement; Pseudoglycals; C-Glycosylations; Glycosides; Thioglycosides
Funding
- Razi University Research Council
- Kermanshah Oil Refining Company
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The reaction of benzyl alcohol with 3,4,6-tri-O-acetyl-d-glucal has been investigated with several heteropoly compounds, and the optimal catalyst is 12-tungstophosphoric acid supported on carbon. In the presence of this catalyst, various alcohols gave the corresponding alkyl and aryl 2,3-unsaturated glycopyranosides in excellent yields and good anomeric selectivity under solvent-free condition. 4,6-Di-O-acetyl-2,3-dideoxy--d-erythro-hex-2-enopyranosyl cyanide and ethyl 4,6-di-O-acetyl-2,3-dideoxy-1-thio--d-erythro-hex-2-enopyranoside have also been prepared with trimethylsilyl cyanide and ethanthiol as nucleophiles, respectively. The catalyst could be easily recovered and reused several times with slight loss of activity. The selectivity to give -anomers predominantly did not show any change in all runs.
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