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Synthesis method of beta-nicotinamide mononucleotide

A single nucleotide and synthesis method technology, applied in chemical instruments and methods, preparation of sugar derivatives, sugar derivatives, etc., can solve problems such as low efficiency and cumbersome operation, achieve high operation efficiency, ensure high yield, The effect of short reaction times

Active Publication Date: 2020-09-11
上海舒泽生物科技研究所
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] The synthesis route of β-nicotinamide mononucleotide provided by the above invention has a yield of 80%. Only after the first treatment or separation can enter the subsequent processing steps, the operation is cumbersome and the efficiency is low

Method used

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  • Synthesis method of beta-nicotinamide mononucleotide

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0035] Embodiment 1: as figure 1 , a synthetic method of β-nicotinamide mononucleotide, the specific steps are as follows:

[0036] S1, add 60g of nicotinamide, 500mL of hexamethyldisilamine and 3.3g of ammonium sulfate into the reaction kettle, mix and stir for 5min, heat up to 117°C, and reflux for 6h;

[0037] S2, add 500mL of dichloromethane and 160g of tetraacetyl ribose into the reaction kettle, add 70mL of tin tetrachloride, heat to 50°C and react for 1.5h, cool to 0°C, add 20mL of methanol to react for 30min;

[0038] S3, add 1000mL of methanol into the above reaction kettle, cool to -8°C, add 60mL of n-propylamine and react for 20h to obtain a reaction solution containing nicotinamide riboside;

[0039] S4, add 300mL trimethyl phosphate into the above reaction kettle, cool to 0°C, add 26.8mL phosphorus oxychloride under the protection of nitrogen, and react at constant temperature for 10h;

[0040] S5, pour the reaction solution obtained in the above steps into rapi...

Embodiment 2

[0042] Embodiment 2: as figure 1 , a synthetic method of β-nicotinamide mononucleotide, the specific steps are as follows:

[0043] S1, add 122g of nicotinamide, 1L of hexamethyldisilamine and 7g of ammonium sulfate into the reaction kettle, mix and stir for 5 minutes, heat up to 117°C, and reflux for 6 hours;

[0044] S2, add 1L of dichloromethane and 315g of tetraacetyl ribose into the reaction kettle, add 150mL of tin tetrachloride, heat to 50°C and react for 1.5h, cool to 0°C, add 40mL of methanol to react for 30min;

[0045] S3, add 2L of methanol into the above reaction kettle, cool to -8°C, add 120mL of n-propylamine and react for 20h to obtain a reaction solution containing nicotinamide riboside;

[0046] S4, add 600mL trimethyl phosphate into the above reaction kettle, cool to 0°C, add 52mL phosphorus oxychloride under the protection of nitrogen, and react at constant temperature for 10h;

[0047] S5, pour the reaction solution obtained in the above steps into rapid...

Embodiment 3

[0049] Embodiment 3: as figure 1 , a synthetic method of β-nicotinamide mononucleotide, the specific steps are as follows:

[0050] S1, add 60g of nicotinamide, 500mL of hexamethyldisilamine and 3.3g of ammonium sulfate into the reaction kettle, mix and stir for 5min, heat up to 125°C, and reflux for 8h;

[0051] S2, add 500mL of dichloromethane and 160g of tetraacetyl ribose into the reaction kettle, add 70mL of tin tetrachloride, heat to 55°C and react for 1.5h, cool to 0°C, add 20mL of methanol to react for 45min;

[0052] S3, add 1000mL of methanol into the above reaction kettle, cool to -5°C, add 60mL of n-propylamine and react for 22h to obtain a reaction solution containing nicotinamide riboside;

[0053] S4, add 300mL trimethyl phosphate into the above reaction kettle, cool to 0°C, add 26.8mL phosphorus oxychloride under the protection of nitrogen, and react at constant temperature for 12h;

[0054] S5, pour the reaction solution obtained in the above steps into rapidl...

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Abstract

The invention discloses a synthesis method of beta-nicotinamide mononucleotide, and relates to the technical field of drug synthesis. The synthesis method mainly comprises the following steps of S1, mixing and reacting nicotinamide, hexamethyldisilazane and a catalyst I in a reaction kettle to obtain silanization-protected nicotinamide; S2, adding tetraacetyl ribose, a solvent, a catalyst II and methanol for reaction so as to generate nicotinamide triacetyl riboside; S3, adding methanol and n-propylamine to generate nicotinamide riboside; S4, adding trimethyl phosphate and phosphorus oxychloride to generate beta-nicotinamide mononucleotide; and S5, separating and purifying the beta-nicotinamide mononucleoside acid. According to the invention, a plurality of continuous steps are controlledto be carried out in one reaction container, and the steps of separating and purifying an intermediate are avoided, so that the method has the advantages of high yield and high production efficiency.

Description

technical field [0001] The invention relates to the technical field of medicine preparation, more specifically, it relates to a synthesis method of β-nicotinamide mononucleotide. Background technique [0002] β-nicotinamide mononucleotide (NMN) is the synthetic substrate of coenzyme I, and NMN is also used in anti-aging research. Keio University in Japan and the University of Washington in the United States cooperated to conduct human clinical trials on the anti-aging effect and safety of β-NMN. Studies have shown that β-nicotinamide mononucleotide can also regulate the secretion of insulin and affect the expression level of mRNA. β-nicotinamide mononucleotide has a wide application prospect in the field of medical treatment. [0003] In the Chinese invention application patent with the publication number CN109053838A, a preparation method of β-nicotinamide mononucleotide is disclosed, which mainly uses ethyl nicotinate and tetraacetyl ribose as starting materials, and unde...

Claims

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Application Information

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IPC IPC(8): C07H19/048C07H1/02C07H1/00B01J27/135
CPCC07H19/048C07H1/02B01J27/135C07H1/00
Inventor 楼秀余
Owner 上海舒泽生物科技研究所
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