Fluorocarbohydrates. Part XIV. Reaction of N-(2-chloro-1,1,2-trifluoroethyl)diethylamine with some O-isopropylidene sugars
- 1 January 1966
- journal article
- research article
- Published by Royal Society of Chemistry (RSC) in Journal of the Chemical Society C: Organic
- Vol. 21, 1994-1997
- https://doi.org/10.1039/j39660001994
Abstract
N-(2-Chloro-1,1,2-trifluoroethyl)diethylamine reacted at room temperature with 1,2:5,6-di-O-isopropylidene-α-D-glucofuranose, 1,2:3,4-di-O-isopropylidene-α-D-galactopyranose, and methyl 3,4-O-isopropylidene-β-L-arabinopyranoside to give the respective 3-, 6-, and 2-O-chlorofluoroacetates. Under alkaline conditions, these compounds were hydrolysed to the parent isopropylidene-sugar and sodium chlorofluoroacetate. The latter was characterised as the S-benzylthiouronium salt. The amine reacted similarly with 1,2-O-isopropylidene(±)-glycerol, giving 3-O-chlorofluoroacetyl-1,2-O-isopropylidene-(±)-glycerol. With 1,2:3,4-di-O-isopropylidene-α-D-galactopyranose in dimethylformamide at 60° in the presence of anhydrous potassium fluoride, the amine gave a mixture from which was isolated 6-chloro-6-deoxy-1,2:3,4-di-O-isopropylidene-α-D-galactopyranose, giving on acid hydrolysis crystalline 6-chloro-6-deoxy-α-D-galactose.Keywords
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