关键词: 钼酸, D-葡萄庚酮糖, 碳链重排, 合成

Abstract: This article reports a new concise method of synthesis of D-glucoheptulose by catalyzed carbon-skeleton rearrangement under the system of MoO3 aqueous solution. Firstly, 2,3:5,6 -Di-O-isopropylidene-D-mannose was prepared from D-mannose as starting material under the catalyst of iodine, with yield 90%. Secondly, hydroxymethylation on C-2 of 2,3:5,6-Di-O-isopropylidene -D-mannose occurred with formaldehyde aqueous solution under base condition, with yield 40%. Thirdly, 2-C-hydroxymethyl-D-mannose was prepared through deprotection of isopropyaltion reaction under acid condition with the yield of 92%. And finally, D-glucoheptulose was synthesized by molybdic acid-catalyzed carbon-skeleton rearrangement with the yield of 56%(total yield 18%). In addition, the acetylated products of 2-C-hydroxymethyl-D-mannose and D-glucoheptulose were characterized by 1HNMR. The advantages of the method included easily acquiring of materials, reducing the reaction procedures, avoiding the application of expensive metal reagents and well foreground of industrial application.

Key words: molybdic acid, D-glucoheptulose, carbon-skeleton rearrangement, synthesis