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Method for preparing L-sorbose from D-glucose

A technology for glucose and sorbose, which is applied in the field of preparing L-sorbose from D-glucose, and can solve problems such as large catalysts

Active Publication Date: 2021-04-23
DALIAN UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

This method requires large amounts of catalysts that are difficult to synthesize

Method used

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  • Method for preparing L-sorbose from D-glucose
  • Method for preparing L-sorbose from D-glucose
  • Method for preparing L-sorbose from D-glucose

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0023] Example 1: Preparation of L-sorbose from D-glucose mediated by Mg(II)

[0024] Under air, 2,3,4,6-tetraoxybenzyl-D-glucose (2mmol, 1.08g) was dissolved in toluene (20mL), and Mg n Bu 2 (1 mmol, 749 mg). The mixture was heated to 80°C for 6h. with saturated NH 4 Cl solution (20 mL) was quenched and the mixture was extracted with ethyl acetate. The organic phase was washed with brine and washed with Na 2 SO 4 After drying and spin-drying, 821 mg of a colorless oily product was obtained by column chromatography, with a yield of 76%.

[0025]

[0026] 1 H NMR (400MHz, CDCl 3 )δ7.35–7.15(m,18H),7.17-7.15(m,2H),4.96(d, J=12.0Hz,1H),4.84(t,J=12.0Hz,2H),4.73(d,J =12.0Hz, 1H), 4.64(d, J= 12.0Hz, 1H), 4.56–4.48(m, 3H), 3.95(t, J=8.0Hz, 1H), 3.78–3.75(m, 2H), 3.65 –3.62(m,1H),3.48(d,J=12.0Hz,1H),3.40(d,J=12.0Hz,1H),3.32(d,J=12.0Hz,1H),3.26(s,1H) . 13 C NMR (101MHz, CDCl 3 )δ 138.7, 138.3, 137.8, 137.4, 128.5, 128.4, 128.4, 128.3, 128.1, 128.0, 127.9, 127.9, 127.8, ...

Embodiment 2

[0027] Example 2: Preparation of L-sorbose using D-glucose combined with Mg(II) and Wittig reagent

[0028] Under air, 2,3,4,6-tetraoxybenzyl-D-glucose (2mmol, 1.08g) was dissolved in toluene (20mL) and Mg n Bu 2 (1 mmol, 749 mg) and benzyl 2-(triphenylphosphimethylene)acetate (0.2 mmol, 82 mg). The mixture was heated to 80°C for 6h. with saturated NH 4 Cl solution (20 mL) was quenched, and the mixture was extracted with ethyl acetate. The organic phase was washed with brine, anhydrous Na 2 SO 4 After drying and spin-drying, 940 mg of a colorless oily product was obtained by column chromatography, with a yield of 87%.

[0029]

[0030] 1 H NMR (400MHz, CDCl 3 )δ7.35–7.15(m,18H),7.17-7.15(m,2H),4.96(d, J=12.0Hz,1H),4.84(t,J=12.0Hz,2H),4.73(d,J =12.0Hz, 1H), 4.64(d, J= 12.0Hz, 1H), 4.56–4.48(m, 3H), 3.95(t, J=8.0Hz, 1H), 3.78–3.75(m, 2H), 3.65 –3.62(m,1H),3.48(d,J=12.0Hz,1H),3.40(d,J=12.0Hz,1H),3.32(d,J=12.0Hz,1H),3.26(s,1H) . 13 C NMR (101MHz, CDCl 3)δ 138.7, 13...

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Abstract

The invention belongs to the technical field of organic synthesis, and provides a method for preparing L-sorbose from D-glucose. The method comprises the following step that in an organic solvent, under the action of a di-n-butyl magnesium catalyst, 2, 3, 4, 6-tetraoxybenzyl-D-glucose is subjected to intramolecular isomerization or subjected to reaction with a Wittig reagent to prepare 1, 3, 4, 5-tetraoxybenzyl-L-sorbose. According to the method, two routes for preparing the 1, 3, 4, 5-tetraoxybenzyl-L-sorbose from the 2, 3, 4, 6-tetraoxybenzyl-D-glucose are very simple and practical, the stereoselectivity is high, the is yield, and the method can be used for large-scale production of the L-sorbose in the industries of pharmacy, chemical engineering and the like.

Description

technical field [0001] The invention belongs to the technical field of organic synthesis, and relates to a new method for preparing L-sorbose from D-glucose, including a method for preparing L-sorbose from D-glucose mediated by Mg(II) and using Mg(II) Method for preparing L-sorbose from D-glucose combined with Wittig reagent. Background technique [0002] L-sorbose is one of the most important natural rare sugars and is mainly used as a starting material for the preparation of vitamin C in the pharmaceutical industry (Journal of Fermentation and Bioengineering. 1996, 81, 351-353). The biotransformation of D-sorbitol into L-sorbose by Gluconobacter suboxidans is a key step in the synthesis of vitamin C by the Reichstein method (Enzyme and Microbial technology. 1990, 12, 322–329). There have been a series of reports on this biotransformation process (Biochemistry. 2006, 45, 13760-13768 and Applied Microbiology and Biotechnology. 2007, 74, 277-281 and Applied Microbiology and ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07H15/18C07H1/00
CPCC07H15/18C07H1/00
Inventor 宋汪泽郑楠郑玉斌孙鑫浩
Owner DALIAN UNIV OF TECH