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Method for preparing 2,3,5-tri-O-tribenzyl-1-chloro-D-arabinofuranose

A technology of arabinofuranose and benzyl, which is applied in the field of preparation of 2,3,5-tri-O-tribenzyl-1-chloro-D-arabinofuranose, which can solve the problem of increased man-hours, decreased yield, and material consumption and increased energy consumption

Inactive Publication Date: 2010-04-21
邓俐丽
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] Obviously, using formula (III) to obtain formula (I) after chlorination has two steps more than using formula (II) to obtain formula (I) after chlorination, material consumption and energy consumption all increase, and required working hours also increase Many, the yield will be greatly reduced

Method used

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  • Method for preparing 2,3,5-tri-O-tribenzyl-1-chloro-D-arabinofuranose
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  • Method for preparing 2,3,5-tri-O-tribenzyl-1-chloro-D-arabinofuranose

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Experimental program
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Effect test

Embodiment 1

[0018] Preparation of 2,3,5-tri-O-benzyl-1-chloro-D-arabinofuranose

[0019] Step 1: 38g (0.1mol) of 2,3,5-tri-O-benzyl-D-arabinofuranose and 200ml of trichloroacetonitrile were placed in a 500ml three-necked flask, and dry hydrogen chloride gas was introduced, heated to reflux, and reacted After 2 hours, the spots of the reactants detected by TLC basically disappeared (toluene / methanol 9:1). Trichloroacetonitrile was recovered under reduced pressure to dryness to obtain 43.0 g of light yellow oil.

[0020] Step 2: Take the oil in the previous step, add 300ml of ethyl acetate, heat to dissolve, add 0.5g of activated carbon, heat to reflux for 20min, filter while it is hot, and after the filtrate is cooled to room temperature, solids begin to precipitate slowly, then use an ice-water bath to dissolve It was cooled to below 0°C, kept for 4 hours, filtered to obtain a white solid, and dried in vacuum at 50°C to obtain 36.5 g of 2,3,5-tri-O-benzyl-1-chloro-D-arabinofuranose (cont...

Embodiment 2

[0022] Preparation of 2,3,5-tri-O-benzyl-1-chloro-D-arabinofuranose

[0023] Step 1: 38g (0.1mol) of 2,3,5-tri-O-benzyl-D-arabinofuranose, 200ml of dichloromethane, placed in a 500ml three-necked flask, cooled in an ice-water bath to below 5°C, and dichloromethane was added dropwise 12.3ml of sulfoxide was added dropwise within 2 hours, and heated to reflux. After 12 hours of reaction, the spots of the reactant basically disappeared as detected by TLC (toluene / methanol 9:1). Return to dichloromethane under reduced pressure and collect to dryness to obtain 45.6 g of light yellow oil.

[0024] Step 2: Take the oil in the previous step, add 300ml of ethyl acetate, heat to dissolve, add 0.5g of activated carbon, heat to reflux for 20min, filter while it is hot, and after the filtrate is cooled to room temperature, solids begin to precipitate slowly, then use an ice-water bath to dissolve It was cooled to below 0°C, kept for 4 hours, filtered to obtain a white solid, and dried in ...

Embodiment 3

[0026] Preparation of 2,3,5-tri-O-benzyl-1-chloro-D-arabinofuranose

[0027] Step 1: 38g (0.1mol) of 2,3,5-tri-O-benzyl-D-arabinofuranose and 200ml of dichloroethane were placed in a 500ml three-necked flask, cooled in an ice-water bath to below 5°C, and two 12.3ml of thionyl chloride was added dropwise within 2 hours, heated to 80°C, stirred for 2.5 hours, and the spots of the reactant basically disappeared as detected by TLC (toluene / methanol 9:1). Return to dichloromethane under reduced pressure and collect to dryness to obtain 44.6 g of light yellow oil.

[0028] Step 2: Take the oil in the previous step, add 300ml of ethyl acetate, heat to dissolve, add 0.5g of activated carbon, heat to reflux for 20min, filter while it is hot, and after the filtrate is cooled to room temperature, solids begin to precipitate slowly, then use an ice-water bath to dissolve It was cooled to below 0°C, kept for 4 hours, filtered to obtain a white solid, and dried in vacuum at 50°C to obtain ...

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Abstract

The invention relates to 2,3,5-tri-O-tribenzyl-1-chloro-D-arabinofuranose, which is used for producing important intermediates of anti-cancer drugs, such as nelarabine, fludarabine, ancitabine and the like. The invention relates to a method for preparing the 2,3,5-tri-O-tribenzyl-1-chloro-D-arabinofuranose. The method can acquire a solid-state target product which is convenient to store, transport and use.

Description

field of invention [0001] The invention relates to a preparation method of an anticancer drug intermediate 2,3,5-tri-O-benzyl-1-chloro-D-arabinofuranose. technical background [0002] 2,3,5-Tri-O-tribenzyl-1-chloro-D-arabinofuranose is used to prepare anticancer drugs such as nelarabine, fludarabine, cytarabine, and adenosine important intermediates. The 2,3,5-tri-O-benzyl-1-chloro-D-arabinofuranose obtained by the existing technology is a kind of oil, which is not convenient for storage, transportation and use. Generally, it is first prepared as follows: The 2,3,5-tri-O-benzyl-1-O-p-nitrobenzoyl-D-arabinofuranose of (III) is temporarily chlorinated to obtain 2,3,5-tri -O-benzyl-1-chloro-D-arabinofuranose (Li Yeqing, Lu Ming, Lu Chunxu, Lu Hongfei. Synthesis of fludarabine. Jiangsu Chemical Industry, 2005, 33(3): 121-123). [0003] [0004] Literature: Li Liwei, Dai Xuyong, Cheng Zhigang. Synthesis of 2,3,5-tri-O-benzyl-1-O-p-nitrobenzoyl-D-arabinofuranose. China Journ...

Claims

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Application Information

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IPC IPC(8): C07H15/18C07H1/00C07H15/203
Inventor 邓俐丽
Owner 邓俐丽
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