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Method for preparing 3,5,6-tri-oxy-benzyl-1,2-isopropylidene-D-glucose

A technology of isopropylidene and glucose, which is applied in the preparation of sugar derivatives, chemical instruments and methods, sugar derivatives, etc., to achieve the effects of simplifying the operation steps, avoiding the generation of by-product hydrogen, and convenient operation

Inactive Publication Date: 2015-03-04
济南尚博医药股份有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] In the above method for preparing 3,5,6-tri-oxo-benzyl-1,2-isopropylidene-D-glucose and the prior art, Most of them are two-phase reactions, and mass transfer is difficult; the strong base sodium hydride used is easy to absorb moisture, and hydrogen gas is released during the reaction process, which is dangerous in production, and because the by-product is hydrogen gas, it must be protected by argon or nitrogen gas, which has high environmental requirements for the reaction system. , the operation is complex

Method used

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  • Method for preparing 3,5,6-tri-oxy-benzyl-1,2-isopropylidene-D-glucose
  • Method for preparing 3,5,6-tri-oxy-benzyl-1,2-isopropylidene-D-glucose

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Embodiment 1

[0018] Add 10g of 1,2-isopropylidene-D-glucose, 7g of sodium carbonate and 2g of tetrabutylammonium iodide into 40g of DMF, add 6g of benzyl bromide dropwise under stirring, and react at 20°C for 20h after the dropwise addition , after the reaction was completed, filtered, concentrated under reduced pressure at 100°C, and the residue was purified by column chromatography, eluting with ethyl acetate:petroleum ether=1:7, and concentrated under reduced pressure to remove the solvent to obtain 3,5,6-tri- Oxy-benzyl-1,2-isopropylidene-D-glucose 19.69g, yield 89.5%.

Embodiment 2

[0020] Add 10g of 1,2-isopropylidene-D-glucose, 5g of sodium carbonate and 1g of tetrabutylammonium iodide into 30g of DMF, add 2g of benzyl bromide dropwise under stirring, and react at 0°C for 20h after the dropwise addition , after the reaction was completed, filtered, concentrated under reduced pressure at 100°C, and the residue was purified by column chromatography, eluting with ethyl acetate:petroleum ether=1:7, and concentrated under reduced pressure to remove the solvent to obtain 3,5,6-tri- Oxy-benzyl-1,2-isopropylidene-D-glucose 19.56g, yield 88.9%.

Embodiment 3

[0022] Add 10g of 1,2-isopropylidene-D-glucose, 5g of sodium hydroxide and 4g of tetrabutylammonium iodide into 30g of DMF, add 8g of benzyl bromide dropwise under stirring, and react at 50°C after the addition is complete 30h, after the reaction is completed, filter, concentrate under reduced pressure at 100°C, and purify the residue by column chromatography, eluting with ethyl acetate:petroleum ether=1:7, and remove the solvent by concentrating under reduced pressure to obtain 3,5,6-tri -Oxy-benzyl-1,2-isopropylidene-D-glucose 19.62 g, yield 89.2%.

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Abstract

The invention provides a method for preparing 3,5,6-tri-oxy-benzyl-1,2-isopropylidene-D-glucose. The method comprises the following steps of adding 1,2-isopropylidene-D-glucose, alkali and tetrabutyl amine iodide into DMF, dropwise adding benzyl bromide under stirring, reacting for 20-35 hours after the dropwise adding is ended, filtering after the reaction is ended, concentrating at 100 DEGC under reduced pressure, purifying residues by column chromatography, removing DMF by concentrating under reduced pressure to obtain 3,5,6-tri-oxy-benzyl-1,2-isopropylidene-D-glucose. The method is characterized in that the alkali is sodium carbonate, sodium hydroxide, potassium hydroxide, barium hydroxide or calcium hydroxide. The method disclosed by the invention adopts sodium carbonate and the like to substitute sodium hydride solids, so that the production of a byproduct hydrogen gas is avoided, the inert gas protection in the reaction process is cancelled, the operation steps are simplified. Moreover, the method is safe and reliable, and convenient to operate.

Description

technical field [0001] The invention belongs to the technical field of chemical synthesis and relates to a method for preparing 3,5,6-tri-oxo-benzyl-1,2-isopropylidene-D-glucose. Background technique [0002] Glucose compounds widely exist in organisms, and many of them are responsible for important biological functions due to their special biological activities. In the document Carbohydrate Research, 125 (1984) 265-282, a kind of 3,5,6-tri-oxo-benzyl-1,2-isopropylidene-D-glucose preparation method is provided, 1,2-isopropylidene Propylene-D-glucose, benzyl chloride, and tetrabutylammonium iodide were added to DMF, benzyl bromide was added dropwise, reacted for 24 hours, filtered, and concentrated. Purified by column chromatography to obtain 3,5,6-tri-oxo-benzyl-1,2-isopropylidene-D-glucose, the reaction formula is as follows: [0003] [0004] In the above-mentioned method for preparing 3,5,6-tri-oxo-benzyl-1,2-isopropylidene-D-glucose and the prior art, most of th...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07H9/04C07H1/00
Inventor 孟庆文郗遵波
Owner 济南尚博医药股份有限公司
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