Canadian Journal of Chemistry p. 1857 - 1862 (1982)
Update date:2022-08-11
Topics:
Martin, Olivier R.
Korppi-Tommola, Sirkka-Liisa
Szarek, Walter A.
5-Deoxy-D-threo-hexulose ("5-deoxyfructose", "5-deoxysorbose") has been prepared in six steps from D-fructose.The reaction of 2,3-O-isopropylidene-β-D-fructopyranose with sulfuryl chloride afforded exclusively 5-chloro-5-deoxy-2,3-O-isopropylidene-α-L-sorbopyranose in the key step. "5-Deoxyfructose" exists only in the 2C5(D) pyranoid form in solution, and was found to be much sweeter than L-sorbose and nearly as sweet as D-fructose.Comments on this unexpected sweetness result are given.
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