294638-87-2Relevant academic research and scientific papers
Glucofuranoses
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, (2008/06/13)
A β-D-glucofuranose compound which is 1,2,3,5,6-penta-O-propanoyl-β-D-glucofuranose, preferably in crystalline form, is prepared from D-glucose. The compound is prepared by reacting D-glucose with boric acid, or an equivalent thereof, followed by treatment with a propanoylating reagent, preferably propanoic anhydride. The compound is useful for the preparation of other compounds, such as glucofuranosides.
The influence of boric acid on the acetylation of aldoses: 'One-pot' syntheses of penta-O-acetyl-β-D-glucofuranose and its crystalline propanoyl analogue
Furneaux, Richard H.,Rendle, Phillip M.,Sims, Ian M.
, p. 2011 - 2014 (2007/10/03)
When glucose and boric acid are heated in acetic acid a soluble compound forms from which, with acetic anhydride and catalytic amounts of sulfuric acid, a mixture consisting of >90% of the glucofuranose per-acetates (α : β ratio 1 : 1.8) is obtained in high yield. In the absence of the sulfuric acid partial acetylation takes place and penta-O-acetyl-β-D-glucofuranose (α: β ratio 1 : 52) is obtainable in good yield by removal of boric acid and completion of the esterification by addition of acetic anhydride and pyridine. A new, crystalline glucofuranose, penta-O-propanoyl-β-D-glucofuranose, is obtained in 58% yield in a 'one-pot' procedure using boric acid. The effects of boric acid on the acid-catalysed acetylation of other aldo-hexoses and -pentoses suggest that the synthesis of furanosyl per-esters could be successful with xylose and idose as well as with glucose.
