Synthesis method of nucleoside diphosphate 6-deoxy-L-pyranose

A nucleoside diphosphate and synthesis method technology, applied in chemical instruments and methods, sugar derivatives, sugar derivatives, etc., can solve the problems of lack of product terminal stereo configuration, low reaction yield, difficult to remove, etc., to achieve The effect of high practical application value

Inactive Publication Date: 2014-01-15
JIANGXI SCI & TECH NORMAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Benefits of technology

This patented process involves reacting certain substances called pyrrolizines or other molecules that have been found to improve their effectiveness for treat diseases such as cancer through chemotherapy. These reactions are faster at room temperature compared to traditional ways like adding sugars during synthetic procedures. Additionally, this novel approach allows for separation between different products without causing unwanted side effects on each one.

Problems solved by technology

This patents describes different ways to make certain types of carbohydrogen polymers called polygnucleated saccharides (PG). These PG structures have unique properties like high water absorption capacity, strong bonding ability with metal atoms involved in catalysis reactions, enzyme activity, etc., making these substances useful building blocks for advanced technologies including drug discovery and development. However, current synthetic techniques require complicated steps involving multiple reactants and involve use of harmful agents during production. There remains room for improvement through more efficient chemistry routes.

Method used

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  • Synthesis method of nucleoside diphosphate 6-deoxy-L-pyranose

Examples

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Embodiment 1

[0012] Uridine 5′-diphosphate-α-L-rhamnose disodium salt 5 The synthesis of N -( O -Benzyl- O -(2′,3′-dibenzyloxycarbonyl)uridine-5′-)phosphorylpiperidine 1 (100 mg, 0.13 mmol), 10% palladium carbon (5 mg, 5% by weight) and triethylamine (18 μL, 0.13 mmol) were dissolved in dry N , N - Dimethylformamide (1 mL), hydrogenated at 20 °C for 3 hours under normal pressure. After hydrogenation, palladium carbon was removed using a filter membrane with a pore size of 0.45 μm, and the solution was added with α-L-rhamnose-1-monophosphate (triethylamine) salt (67 mg, 0.195 mmol), 4,5-dicyanoimidazole ( 61 mg, 0.52 mmol) was stirred at 30°C for 6 hours. After the reaction, the solvent was concentrated. Sodium acetate aqueous solution (10 M, 0.5 mL) was added to the residue to dissolve it, and ethanol (50 mL) was added to precipitate the product, and centrifuged to obtain crude uridine 5′-diphosphate-α-L-rhamnose sodium salt. Using reversed-phase HPLC (XTerra Prep MS C18 OBD TM 1...

Embodiment 2

[0014] Thymidine 5′-diphosphate-α-L-rhamnose disodium salt 6 The synthesis of N -( O -Benzyl- O -(3′-Benzyloxycarbonyl)thymidine-5′-)phosphorylpiperidine 2 (80 mg, 0.13 mmol), 5% palladium carbon (8 mg, 10% by weight) and tri-n-propylamine (25 μL, 0.13 mmol) were dissolved in dry N , N - Dimethylformamide (1 mL), hydrogenated at 30 °C for 2 hours under normal pressure. After hydrogenation, palladium carbon was removed using a filter membrane with a pore size of 0.45 μm, and the solution was added with α-L-rhamnose-1-monophosphate (triethylamine) salt (67 mg, 0.195 mmol), 4,5-dicyanoimidazole ( 61 mg, 0.52 mmol) was stirred at 40°C for 4 hours. After the reaction, the solvent was concentrated. Add sodium acetate aqueous solution (10 M, 0.5 mL) to the residue to dissolve, add ethanol (50 mL) to precipitate the product, and centrifuge to obtain the crude thymidine 5′-diphosphate-α-L-rhamnose sodium salt. Using reversed-phase HPLC (XTerra Prep MS C18 OBD TM 10 μm, 19 × 2...

Embodiment 3

[0016] Uridine 5′-diphosphate-6-deoxy-α-L-talose disodium salt 7 The synthesis of N -( O -Benzyl- O -(2′,3′-dibenzyloxycarbonyl)uridine-5′-)phosphorylpiperidine 1 (100 mg, 0.13 mmol), 10% palladium on carbon (10 mg, 10% by weight) and diisopropylethylamine (21 μL, 0.13 mmol) were dissolved in dry N , N -Dimethylformamide (1 mL), hydrogenated at 40 °C for 1 hour under normal pressure. After hydrogenation, palladium carbon was removed using a filter membrane with a pore size of 0.45 μm, and the solution was added with 6-deoxy-α-L-talose-1-monophosphate (triethylamine) salt (89 mg, 0.26 mmol), 4,5-di Cyanoimidazole (77 mg, 0.65 mmol) was stirred at 30°C for 6 hours. After the reaction, the solvent was concentrated. Sodium acetate aqueous solution (10 M, 0.5 mL) was added to the residue to dissolve it, and then ethanol (50 mL) was added to precipitate the product, and centrifuged to obtain crude uridine 5′-diphosphate-6-deoxy-α-L-talose sodium salt. Using reversed-phase HP...

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Abstract

The invention belongs to the field of chemical synthesis, and relates to a synthesis method of nucleoside diphosphate saccharide. The synthesis method comprises the following steps: 1) taking fully-protected nucleoside phosphoryl piperidine, removing all protecting groups through palladium carbon catalytic hydrogenation in an N,N-dimethylformamide or dimethylsulfoxide solution, and filtering to remove palladium and carbon to obtain corresponding deprotected nucleoside phosphoryl piperidine; 2) adding glycosyl-1-monophosphate and 4, 5-dicyanoimidazole (DCI) into the nucleoside phosphoryl piperidine, and reacting to obtain a nucleoside diphosphate saccharide product; 3) performing ethanol precipitation, reverse phase C18HPLC (high performance liquid chromatography) purification and final ion exchange on a crude product to obtain corresponding nucleoside diphosphate 6-deoxy-L-pyranose with high purity. By the synthesis method, the yield is high, the reaction time is short and the product separation is simple; therefore, the synthesis method has a high application value.

Description

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Claims

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Application Information

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Owner JIANGXI SCI & TECH NORMAL UNIV
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