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Process for producing 2-deoxyaldose compound

A technology of alkaline earth metals and general formulas, which is applied in the preparation of sugar derivatives, chemical instruments and methods, monosaccharides, etc., can solve the problems of unsatisfactory safety and economic efficiency, unsatisfactory, high cost, etc., to achieve Excellent volumetric efficiency, easy recycling, and less waste

Inactive Publication Date: 2005-11-02
MITSUI CHEM INC
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The problem of this method is that not only the cost is high, but also need to use an excessive amount of sodium borohydride (11.5 equivalents relative to 2-keto-3-deoxy-D-potassium gluconate) to decompose and produce hydrogen, which is difficult to achieve in terms of safety and economy. less than satisfied
In addition, the use of water equivalent to 2000 times the weight of 2-keto-3-deoxy-D-gluconate potassium has a very low volumetric efficiency and is not satisfactory as an industrial production method
On the other hand, the product metasaccharinic acid is not described, and the yield is not clear

Method used

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  • Process for producing 2-deoxyaldose compound
  • Process for producing 2-deoxyaldose compound
  • Process for producing 2-deoxyaldose compound

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0090] [Example 1] Contact hydrogenation of 2-keto-3-deoxy-D-gluconic acid

[0091] Add 50 mg of 10% palladium carbon (48% aqueous product) to 5.0 g of a 10% aqueous solution of 2-keto-3-deoxy-D-gluconic acid (hereinafter referred to as KDG), and heat to an internal temperature of 48°C. After reacting under hydrogen flow for 9 hours, the reaction solution was analyzed by HPLC, and the reaction yield of metasaccharic acid lactone was 54%, and the reaction yield of metasaccharic acid was 26%.

[0092] HPLC analysis conditions: Shodex Asahipack NH2-P50 (manufactured by Showa Denko), 50 mM sodium phosphate aqueous solution, flow rate 1 ml / min, UV210 nm detection.

Embodiment 2

[0093] [Example 2] The contact hydrogenation of KDG

[0094] The reaction was carried out in the same manner as in Example 1 except that 45 µl of sulfuric acid was added. The reaction solution was analyzed by HPLC, and the reaction yield was 92% of the mixture of metasaccharic acid lactone and metasaccharic acid.

Embodiment 3

[0095] [Example 3] The contact hydrogenation of KDG

[0096] The reaction was carried out in the same manner as in Example 1 except that 107 µl of sulfuric acid was added. The reaction solution was analyzed by HPLC, and the reaction yield was 96% of the mixture of metasaccharic acid lactone and metasaccharic acid.

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Abstract

An object of the present invention is to provide a method for preparing 2-deoxyaldoses on industrial scale in which the yield or the volumetric efficiency is excellent and the operation is simple, as compared to the conventionally known preparation method. A compound represented by the general formula (1) such as 2-keto-3-deoxygluconic acid or the like is reduced by the catalytic hydrogenation method using a metal such as palladium or the like, or a compound represented by the general formula (1) such as 2-keto-3-deoxygluconic acid or the like is reduced by using a hydride reducing agent in a solvent of not more than 30 weight times the amount of the above compound, for synthesizing 2-keto-3-deoxyaldonic acid. The 2-keto-deoxyaldonic acid was decarboxylated to obtain 2-deoxyaldoses. The method of the present invention is economical and efficiently excellent.

Description

technical field [0001] The present invention relates to the preparation method of 2-deoxyaldose. Background technique [0002] When synthesizing sugars, it is common to attach a protective group to a hydroxyl group contained in the compound in order to allow the desired reaction to proceed. In the synthesis of 2-deoxyaldose, the synthesis method of protecting hydroxyl group with acyl group or acetyl group has also been reported, but it is not preferred as an industrial preparation method due to the need for deprotection and purification, which increases the number of steps. Therefore, a production route without using a protecting group is advantageous as an industrial production method. From this point of view, a representative example of the prior art includes alkali decomposition of glucose, acidification to obtain metasaccharinolactone, hydrolysis, and iron-catalyzed decomposition to obtain 2-deoxyribose. (J. Am. Chem. Soc., (1954), Vol. 76, p. 3541). However, the alka...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D307/33C07H1/00C07H3/02
CPCC07H1/00C07D307/33C07H3/02
Inventor 梅谷豪毅小松弘典安藤知行富樫和彦
Owner MITSUI CHEM INC
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