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Preparation method of beta-nicotinamide ribose chloride (NRC)

A nicotinamide ribose and chloride technology is applied in the preparation of sugar derivatives, chemical instruments and methods, sugar derivatives, etc., and can solve the problems of high cost, low yield, difficult handling, etc., and achieves low production cost and high purity. , the effect of low equipment requirements

Active Publication Date: 2020-01-03
武汉一若生物材料有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0007] These methods have been described and reported in the literature in detail, but there are problems such as low yield, high cost, difficult post-reaction treatment or the need to pass through chromatographic columns and freeze-drying, which limit their use in large-scale industrial production.

Method used

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  • Preparation method of beta-nicotinamide ribose chloride (NRC)
  • Preparation method of beta-nicotinamide ribose chloride (NRC)
  • Preparation method of beta-nicotinamide ribose chloride (NRC)

Examples

Experimental program
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Effect test

Embodiment 1

[0052] A preparation method of β-nicotinamide ribose chloride, the steps are as follows:

[0053] a. Chlorination reaction

[0054] Dissolve 2kg of tetraacetylribose (supplied by Wuxi Jingyao Biotechnology Co., Ltd., the same below) in 10L of chloroform, control the temperature in an ice-water bath at 0°C, inject hydrogen chloride gas to saturation, and continue the reaction for 2 hours. TLC monitoring shows that the raw material Disappeared, spin dry chloroform at 30-35°C, collect the evaporated chloroform; add 3L toluene to the reaction system in 4 times for vacuum distillation, water bath temperature 40-45°C, take away the chloroform in the system by vacuum distillation Acetic acid, spin-dried to obtain 1.79 kg of oily triacetyl ribose chloride, with a yield of 96.5%, all of which were directly used in the next step.

[0055] b. Condensation reaction

[0056] Under the protection of nitrogen, add the chlorinated triacetyl ribose and 0.6kg of nicotinamide obtained in the p...

Embodiment 2

[0062] Embodiment 2 (large batch):

[0063] A preparation method of β-nicotinamide riboside, the steps are as follows:

[0064] a. Chlorination reaction

[0065] Dissolve 200kg of tetraacetylribose in 700L of dichloromethane, control the temperature in an ice-water bath at 0°C, pass in hydrogen chloride gas to saturation, and continue the reaction for 2 hours. TLC monitoring shows that the raw materials have disappeared. Evaporate the dichloromethane to dryness at 30-35°C. dichloromethane; 300L toluene was added to the reaction system in 4 times for vacuum distillation, the water bath temperature was 40-45°C, and the acetic acid in the system was taken away by vacuum distillation, and the oil obtained by spin-drying was chlorotriacetyl ribose 183 kg, with a yield of 98.6%, all of which were directly used in the next reaction.

[0066] b. Condensation reaction

[0067] Under the protection of nitrogen, add the chlorinated triacetyl ribose and 60kg of nicotinamide obtained in...

Embodiment 3

[0074] A preparation method of β-nicotinamide riboside, the steps are as follows:

[0075] a. Chlorination reaction

[0076] Dissolve 2kg of tetraacetylribose in 10L of dichloromethane, control the temperature in an ice-water bath at 0°C, and inject hydrogen chloride gas to saturation. TLC monitoring shows that the raw material has disappeared, spin dry the dichloromethane at about 30-35°C, and collect the evaporated dichloromethane. Chloromethane; 3L of toluene was added to the reaction system in 4 times for rotary evaporation, the water bath temperature was 40-45°C, and the acetic acid in the system was taken away by vacuum distillation, and the oil obtained by spinning was 1.81 kg of chlorotriacetyl ribose, and the yield was It was 97.6%, all of which were directly used in the next reaction.

[0077] b. Condensation reaction

[0078] Under the protection of nitrogen, add the chlorinated triacetyl ribose and 0.6kg of nicotinamide obtained in the previous step into 3L of ac...

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Abstract

The invention belongs to the field of chemical synthesis, and particularly relates to a preparation method of beta-nicotinamide ribose chloride (NRC). The technical problem of low-cost high-efficiencysynthesis of the beta-NRC for industrial tonnage production is solved. The preparation method includes the main steps that tetraacetylribose is chlorinated, then condensed with nicotinamide, then a deacetylation reaction is carried out, and the beta-NRC is obtained. The preparation method has the advantages of simple operation, easy amplified production, low cost, good finished product quality and the like.

Description

technical field [0001] The invention relates to the technical field of chemical synthesis, in particular to a preparation method of β-nicotinamide ribose chloride. Background technique [0002] Scientists have discovered that almost all anti-aging methods and concepts are inseparable from a crucial substance, that is NAD+. The full name of NAD+ is "nicotinamide adenine dinucleotide", which is a coenzyme. Studies have found that the precursor of NAD+ (NMN) can reverse aging, and β-nicotinamide ribose chloride (NRC) is a derivative of vitamin B3, which can be used as a precursor of NMN for the synthesis of NMN, and it is also the Precursor substrate for factor nicotinamide adenine dinucleotide (NAD+). Can increase NAD+ levels after ingestion. Taking nicotinamide riboside chloride directly can increase the content of nicotinamide adenine dinucleotide (NAD+) in the human body by 60%. A large number of studies have shown that β-nicotinamide ribose chloride can enhance the met...

Claims

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Application Information

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IPC IPC(8): C07H1/00C07H1/06C07H19/048
CPCC07H1/00C07H1/06C07H19/048
Inventor 杜小兰程进
Owner 武汉一若生物材料有限公司
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