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Citation: CHENG Jie, FANG Zhi-Jie, JIAO Yan, JIANG Yu-Hua, ZHENG Bao-Hui. Concise Synthesis of D-Glucoheptulose under Molybdic Acid-Catalysis[J]. Chinese Journal of Applied Chemistry, ;2009, 26(7): 749-752. shu

Concise Synthesis of D-Glucoheptulose under Molybdic Acid-Catalysis

1.
School of Chemical Engineering, Nanjing University of Science & Technology, Nanjing 210094

Corresponding author: FANG Zhi-Jie,
Received Date: 18 June 2008
Available Online: 20 August 2008

This article reports a method for the synthesis of D-glucoheptulose by catalyzing carbon-skeleton rearrangement in 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 a yield of 90%.Secondly,hydroxymethylation on the C-2 of 2,3:5,6-Di-O-isopropylidene-D-mannose occurred with formaldehyde aqueous solution under base condition,with a yield of 40%.Thirdly,2-C-hydroxymethyl-D-mannose was prepared through the deprotection of isopropyaltion reaction under acid condition with a yield of 92%.And finally,D-glucoheptulose was synthesized by molybdic acid-catalyzed carbon-skeleton rearrangement with a yield of 56%(total yield 18%).In addition,the acetylated products of 2-C-hydroxymethyl-D-mannose and D-glucoheptulose were characterized by ¹H NMR.The advantages of the method includ readily acquiring of materials,simplifying of the reaction procedures,and avoiding the application of expensive metal reagents with a good foreground of industrial application.
- molybdic acid,
- D-glucoheptulose,
- carbon-skeleton rearrangement,
- synthesis
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