Synthetic method of Jjar mycin

A jaspamycin and synthetic method technology, applied in the field of nucleoside compound synthesis, can solve the problems of long reaction steps and high cost, and achieve the effect of short route steps, cheap reagents and simple reaction conditions

Pending Publication Date: 2021-05-28
KANGHUA SHANGHAI DRUG RES DEV CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0003] The purpose of the present invention is to provide a synthetic method of jasperamycin, which mainly solves the technical problems of long reaction steps and high cost in the present synthetic method

Method used

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  • Synthetic method of Jjar mycin
  • Synthetic method of Jjar mycin

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0014] Example 1: Jaspamycin.

[0015] step 1:

[0016] N,O-bis(trimethylsilyl)acetamide (34 ml, 134 mmol) was added to 4-chloro-5-iodo-7H-pyrrolo[2,3-d]pyrimidine (34 g , 120 mmol) in a suspension in acetonitrile (1 L). To this was added 1-acetyl-2,3,5-tribenzoyloxy-1-beta-D-ribofuranose (72 g, 140 mmol) and trimethyl trifluoromethanesulfonate after 10 min Silica ester (25.5ml, 134mmol). After the reaction solution was stirred at room temperature for 15 minutes, the temperature was raised to 80° C. for 18 hours. The reaction solution was cooled to room temperature, diluted with ethyl acetate and poured into saturated aqueous sodium bicarbonate solution for liquid separation. The organic phase was washed with brine, dried and concentrated. The resulting residue was slurried in methanol and filtered to obtain compound 1 (79 g, 90% yield) as a white solid.

[0017] Step 2:

[0018] Compound 1 (79 g, 109 mmol) was dispersed in methanol (2 L), sodium methoxide (60 g, 109 mm...

Embodiment 2

[0023] Example 2, the reaction temperature of step 1 is 75°C, and the reaction time is 24 hours; the reaction temperature of step 2 is 30°C, and the reaction time is 12 hours; the step 3 is refluxed for 1 hour, and the reaction temperature of step 4 is 110°C, and the reaction time is 30 hours ; All the other are with embodiment 1.

Embodiment 3

[0024] Example 3, the reaction temperature of step 1 is 85°C, and the reaction time is 12 hours; the reaction temperature of step 2 is 20°C, and the reaction time is 24 hours; the reaction temperature of step 3 is refluxed for 2 hours; the reaction temperature of step 4 is 100°C, and the reaction time is 36 hours. All the other are with embodiment 1.

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Abstract

The invention relates to a synthetic method of jjar mycin. The technical problems of long steps and high cost of the existing synthesis method are mainly solved. The synthesis method comprises the following synthesis steps: generating a compound 1 from 4-chloro-5-iodine-7H-pyrrolo [2, 3-d] pyrimidine and 1-acetyl-2, 3, 5-tribenzoyloxy-1-beta-D-ribofuranose under the action of N, O-bis (trimethylsilyl) acetamide and trimethylsilyl trifluoromethanesulfonate, and pulping and purifying the product; reacting the compound 1 with sodium methoxide in methanol to obtain a compound 2 without purification; heating and reacting the compound 2 in a sodium hydroxide aqueous solution to generate a compound 3, and pulping and purifying the product; heating and reacting the compound 3 and cuprous cyanide in pyridine, pulping an obtained crude product, and recrystallizing to obtain a target product.

Description

technical field [0001] The present invention relates to the field of synthesis of nucleoside compounds, in particular to a synthesis method of Jaspamycin (English name: Jaspamycin, cas number: 22242-96-2). Background technique [0002] Nucleoside compounds are widely used in antiviral drug research due to their biological activity. Jasperamycin, a potent PKA activator, was recently discovered to be a powerful inducer of cell permeability (Nat Commun. 2019 Mar 29;10(1):1421), a medically overlooked important Exploring PKA signaling independent of cAMP in pathogens brings new ideas for the treatment of some diseases. The currently reported synthetic method of jasperamycin is to prepare tetracyanoethylene (~3000 yuan / 100g) through 8 steps (Tetrahedron Letters, 2013, vol. 54, # 40, p.5484 – 5488; Bioorganic Chemistry, 2007, vol. 35, # 1, p. 25 - 34), multi-step column chromatography purification is required, the overall yield is low, the production cost is very high, and dange...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07H1/00C07H19/14
CPCC07H1/00C07H19/14
Inventor 徐红岩王鹏涛
Owner KANGHUA SHANGHAI DRUG RES DEV CO LTD
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