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Derivative of 2-deoxy-D-ribose, preparation method and application thereof

A kind of use, ribose technology, applied in the field of 2-deoxy-D-ribose derivatives and its preparation, can solve the problems of rising cost, reducing yield, increasing feeding amount, etc.

Inactive Publication Date: 2009-11-04
SHANGHAI INST OF PHARMA IND
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The generation of these pyranose impurities not only reduces the yield of the above reaction, but also the pyranose impurities are generally difficult to remove or remove.
If the desired furanose product mixed with pyranose impurities is used as a raw material for the subsequent reaction, it will be forced to increase the amount of other reaction raw materials and reagents needlessly when feeding, resulting in an increase in cost; in addition, it will also increase the subsequent reaction Difficulty and cost of separation and purification of the reaction

Method used

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  • Derivative of 2-deoxy-D-ribose, preparation method and application thereof
  • Derivative of 2-deoxy-D-ribose, preparation method and application thereof
  • Derivative of 2-deoxy-D-ribose, preparation method and application thereof

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preparation example Construction

[0064] The preparation method of the compound of formula V provided by the present invention is to firstly carry out acetylation protection on the 3 and 5 hydroxyl groups of 1-O-methyl-2-deoxy-D-ribose (compound 2) to obtain the compound of formula IV, and then The 1-position methoxyl group of formula IV compound is converted into substituted acetoxyl group (OR 2 ) to obtain formula V compound:

[0065]

[0066] The preparation of compound 2 has been reported in literature (for example, Synthetic Communication, 1997, 27(20): 3505-3511); compound 2 and anhydride R 1 -O-R 1 or acid halide R 1 -X (preferably anhydride R 1 -O-R 1 ) are mixed in an organic solvent, and reacted for 10-60 hours (preferably 15-48 hours) in the presence of a deacidifying agent to obtain a compound of formula IV. The organic solvent includes various aprotic solvents. The aprotic solvent mentioned is selected from halogenated alkanes (such as dichloromethane, 1,2-ethylene dichloride, etc.), hydr...

Embodiment 1

[0125] Preparation of 1-O-acetyl-3,5-di-O-methoxyacetyl-2-deoxy-D-ribose (4)

[0126]

Embodiment 11

[0128] Preparation of 1-O-methyl-2-deoxy-D-ribose (2)

[0129] Add 2-deoxy-D-ribose (1) (300 g) to methanol (3.6 L), then add 1% methanolic hydrogen chloride solution (600 ml), and stir at room temperature for 25 minutes under nitrogen protection. Sodium bicarbonate (120 g) was added and stirred for 10 minutes. filter. The obtained filtrate was concentrated under reduced pressure to obtain oil 2 (331 g), which was directly used in the next step.

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Abstract

The invention discloses a derivative of 2-deoxy-D-ribose, a preparation method and an application thereof. The derivative is a compound shown as the formula V, wherein R1 and R2 are respectively selected from CH3(CH2)nCO-, CH3(CH2)n-Y-CH2CO-, X-CH2CO-, CH3(CH2)nCH(X)CO-, X2-CHCO-, CH3(CH2)nC(X)2CO-, or CX3CO-; Y is selected from oxygen or sulfur, X is selected from fluorine, chlorine, bromine or iodine, n is from 0 to 5, and R1 is not equal to R2. The invention also discloses a preparation method, an application of the derivative, and a method for preparing decitabine by using the derivative as an intermediate.

Description

technical field [0001] The present invention relates to a new compound, in particular to a derivative of 2-deoxy-D-ribose and its preparation method and use. Background technique [0002] It has been reported in the literature (Journal of Medicinal Chemistry, 1985, 28 (7): 904-910) 2-deoxy-D-ribose (compound 1) 1, 3, 5 triacetyl compounds, but other 2-deoxy- The 1, 3, and 5-position three (substituted acetylated) substances of D-ribose have not been reported, and there are no reports about the three (substituted acetylated) substances with different substituents at the 1, 3, and 5-positions. [0003] In addition, the purity of the 2-deoxy-D-ribose (compound 1) 1, 3, and 5-position triacetyl compound obtained by the preparation method reported in the literature (Journal of Medicinal Chemistry, 1985, 28 (7): 904-910) is not high. High, which contains more of a pyranose impurity (see the figure below). The pyranose impurities are similar in structure and properties to the des...

Claims

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Application Information

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IPC IPC(8): C07H13/06C07H19/12
Inventor 张庆文益兵袁博
Owner SHANGHAI INST OF PHARMA IND
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