89752-93-2Relevant academic research and scientific papers
ACETAL AND ESTER PROTECTING-GROUPS IN THE HYDROGEN FLUORIDE-CATALYSED SYNTHESIS OF D-FRUCTOSE AND L-SORBOSE DIFURANOSE DIANHYDRIDES
Defaye, Jacques,Gadelle, Andree,Pedersen, Christian
, p. 323 - 330 (1988)
Treatment of acetylated inulin with anhydrous hydrogen fluoride under mild conditions gave a good yield of tri-O-acetyl-α-D-fructopyranose tri-O-acetyl-β-D-fructofuranose 1,2':2,1'-dianhydride together with smaller amounts of the corresponding β,β-anomer.When 2,3:4,6-di-O-isopropylidene-α-L-sorbofuranose was treated with hydrogen fluoride under similar conditions, with a short reaction time, α-L-sorbofuranose β-L-sorbofuranose 1,2':2,1'-dianhydride was obtained.A longer reaction time led to a rearranged product, di-α-L-sorbofuranose 2,1':3,2'-dianhydride.
THE BEHAVIOR OF L-SORBOSE TOWARDS ANHYDROUS HYDROGEN FLUORIDE
Defaye, Jacques,Gadelle, Andree,Pedersen, Christian
, p. 89 - 98 (2007/10/02)
L-Sorbose was converted into a mixture of L-sorbose dianhydrides by treatment with anhydrous hydrogen fluoride.Of the six dianhydrides isolated, two were known compounds.The structures have been established by n.m.r. spectroscopy.The relative amounts of dianhydrides obtained depended on the reaction conditions.By use of 13C-n.m.r. spectroscopy, the reaction of L-sorbose with hydrogen fluoride was shown to involve L-sorbofuranosyl fluoride as an intermediate.Dianhydrides were also formed when L-sorbose was treated with methanol and sulfuric acid under Fischer glycosidation condition, or with trifluoroacetic acid.
