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Preparation method of 1,2,5-O-triacyl-3-deoxy-alpha-D-xylofuranose

A 5-O-, xylofuranose technology, applied in 1 field, can solve the problems of complex reaction or post-processing, strong environmental pollution, high processing cost, etc., and achieve the effect of simple and feasible preparation method, easy industrialization, and environmental friendliness

Active Publication Date: 2012-10-03
CHINA GATEWAY PHARMA DEV CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0017] The technical problem to be solved by the present invention is to overcome the toxicity of reagents used in the existing method for preparing 1,2,5-O-triacyl-3-deoxy-α-D-xylfuranose, strong environmental pollution, Due to the defects of high processing cost, complex reaction or post-treatment, difficult product purification or difficult industrialization, it provides a simple, feasible, low cost, high yield, high purity, environmentally friendly and easy to industrialize preparation1,2 , the method of 5-O-triacyl-3-deoxy-α-D-xylofuranose

Method used

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  • Preparation method of 1,2,5-O-triacyl-3-deoxy-alpha-D-xylofuranose

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0028] Example 1 Compound II (R 1 =R 2 =Methyl) Preparation

[0029] Compound I (R 1 = Methyl) (0.1mol) was added to a 100ml reaction flask. Add acetic anhydride (0.1 mol) and DMAP (0.01 mol) under cooling (0°C). Then, concentrated sulfuric acid (0.1 mol) with a mass fraction of 90% was added dropwise, and the dropping rate was controlled to keep the internal temperature below 0°C. After the internal temperature was slowly raised to room temperature (20-25° C.), the reaction was stirred for 3 hours until TLC tracked the complete reaction of the raw materials, and saturated brine was added to the reaction solution under cooling with ice brine, and stirred for 3 hours. Then it was extracted with ethyl acetate, washed with sodium carbonate aqueous solution to pH 6.5-7.5, dried and concentrated to obtain the target compound as a pale yellow liquid with a yield of 72% and a purity of HPLC: 94.7%.

Embodiment 2

[0030] Example 2 ``Compound II (R 1 =R 2 =Methyl) Preparation

[0031] Compound I (R 1 = Methyl) (0.1mol) was added to a 100ml reaction flask. Add acetic anhydride (0.2mol) and DMAP (0.01mol) under ice-salt bath cooling (-10°C). Then, concentrated sulfuric acid (0.2 mol) with a mass fraction of 90% was added dropwise, and the dropping rate was controlled to keep the internal temperature below 0°C. After the internal temperature was slowly raised to room temperature (25-30°C), the reaction was stirred for 2 hours until the TLC tracked the complete reaction of the raw materials, and saturated brine was added to the reaction solution under cooling with ice brine, and stirred for 3 hours. Then it was extracted with ethyl acetate, washed with sodium carbonate aqueous solution to pH 6.5-7.5, dried and concentrated to obtain the target compound as a pale yellow liquid with a yield of 75% and HPLC: 94.1%.

Embodiment 3

[0032] Example 3 "Compound II (R 1 =R 2 = Ethyl) Preparation

[0033] Compound I (R 1 = Ethyl) (0.1mol) was added to a 100ml reaction flask. Add propionic anhydride (0.15 mol) and DMAP (0.015 mol) under ice-salt bath cooling (-5°C). Then, concentrated sulfuric acid (0.2 mol) with a mass fraction of 95% was added dropwise, and the dropping rate was controlled to keep the internal temperature below 0°C. After the internal temperature was slowly raised to room temperature (20-25° C.), the reaction was stirred for 4 hours until the TLC tracked the complete reaction of the raw materials, and saturated brine was added to the reaction solution under cooling with ice brine, and stirred for 3 hours. Then it was extracted with ethyl acetate, washed with sodium carbonate aqueous solution to pH 6.5-7.5, dried and concentrated to obtain the target compound as a pale yellow liquid, with a yield of 70%, and HPLC: 92.6%.

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Abstract

The invention discloses a preparation method of the 1,2,5-O-triacyl-3-deoxy-alpha-D-xylofuranose represented by the following formula (II). The preparation method comprises the following steps of: at the temperature of 10-40 DEG C, in the presence of 4-(N,N-dimethylamino)pyridine, reacting the compound represented by the following formula (I) with acid anhydride, adding concentrated sulfuric acid, and reacting at 0-60 DEG C to obtain the compound represented by the following formula (II). The method of the invention is simple and feasible, has relatively low cost, high yield, high purity, environmental friendliness and easy industrialization. R1 and R2 are independently methyl, ethyl, propyl, isopropyl, butyl, tertiary butyl, phenyl, benzyl, o-chlorobenzoyl, m-chlorobenzoyl, p-chlorobenzoyl, o-bromobenzoyl, m-bromobenzoyl, p-bromobenzoyl, o-methoxybenzyl, m-methoxybenzyl, p-methoxybenzyl, o-nitrobenzyl, m-nitrobenzyl, p-nitrobenzyl, phenethyl, cyclopentyl or cyclohexyl.

Description

Technical field [0001] The invention relates to a preparation method of 1,2,5-O-triacyl-3-deoxy-α-D-xylofuranose. Background technique [0002] 1,2,5-O-Triacyl-3-deoxy-α-D-xylofuranose (II) has the following structural formula: [0003] [0004] Where R 1 And R 2 The independent ones are methyl, ethyl, propyl, isopropyl, butyl, tert-butyl, phenyl, benzyl, o-chlorobenzyl, m-chlorobenzyl, p-chlorobenzyl, o-bromide Benzyl, m-bromobenzyl, p-bromobenzyl, o-methoxybenzyl, m-methoxybenzyl, p-methoxybenzyl, o-nitrobenzyl, m-nitro Benzyl, p-nitrobenzyl, phenethyl, cyclopentyl or cyclohexyl. [0005] The compound is a commonly used intermediate in the field of drug synthesis, and is particularly widely used in the preparation of antibiotics for the treatment of bacterial infections, anti-AIDS drugs, and cancer diagnostic drugs. [0006] There are two types of synthesis methods reported in the literature so far about 1,2,5-O-triacyl-3-deoxy-α-D-xylofuranose, which are prepared from xylose and ...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07H13/04
Inventor 刘国斌屈博磊李原强
Owner CHINA GATEWAY PHARMA DEV CO LTD