Structure-sweetness relationships for fructose analogs. Part I. Synthesis and evaluation of sweetness of 5-deoxy-D-threo-hexulose

…, SL Korppi-Tommola, WA Szarek

Index: Martin, Olivier R.; Korppi-Tommola, Sirkka-Liisa; Szarek, Walter A. Canadian Journal of Chemistry, 1982 , vol. 60, p. 1857 - 1862

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Citation Number: 23

Abstract

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 2 C 5 (d) pyranoid form in solution, and was found to be much sweeter than l-sorbose and nearly as sweet as d-fructose. Comments on ...