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Process for producing glucal

A technology of glucosinolate and glucose, which is applied in the direction of organic chemistry, can solve the problems of cumbersome operation, high cost, and low yield, and achieve the effects of shortening the process flow, low cost, and short reaction time

Inactive Publication Date: 2010-01-13
CHENGDU INST OF BIOLOGY CHINESE ACAD OF S
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0017] The purpose of the present invention is to solve the disadvantages of high cost, cumbersome operation and low yield in the preparation method of glucal, and provide a simple and effective method for synthesizing glucal with cheap raw materials and high yield

Method used

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  • Process for producing glucal
  • Process for producing glucal
  • Process for producing glucal

Examples

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Effect test

example 1

[0026] Example 1: Add 40mL phosphate buffer solution (the weight ratio of disodium hydrogen phosphate, sodium dihydrogen phosphate to water is 11:14:100) in a 100mL round bottom flask, add 2.1g zinc powder, 0.21g copper sulfate , stirred, then added 2.1g 1-bromoacetylglucose, stirred at room temperature for 8 hours, after TLC detected that the reaction was complete, added 2.1g NaOH to the above reaction solution, and stirred at room temperature for 3 hours. After purification by silica gel column, 0.717 g of pure glucal sugar was obtained with a yield of 96%.

example 2

[0027] Example 2: Add 20mL phosphate buffer solution (the weight ratio of disodium hydrogen phosphate, sodium dihydrogen phosphate to water is 11:14:100) in a 100mL round bottom flask, add 1.0g zinc powder, 0.1g copper sulfate , stirred, then added 1.0 g of 1-bromoacetylglucose, and stirred at room temperature for 5 hours. After the reaction was complete as detected by TLC, 1.0 g of KOH was added to the above reaction solution, and stirred at room temperature for 1.5 hours. Purified by a silica gel column to obtain 0.334 g of pure glucuronose with a yield of 94%.

example 3

[0028] Example 3: Add 2.0g of sodium dihydrogen phosphate, 10mL of water, and 1.0g of zinc powder into a 50mL round bottom flask, stir, then add 1.0g of 1-bromoacetylglucose, stir at room temperature for 0.5 hours, and detect the reaction by TLC After completion, 1.0 g of KOH was added to the above reaction solution, and the reaction was stirred at room temperature for 0.5 hours. Purified by a silica gel column to obtain 0.312 g of pure glucal sugar with a yield of 88%.

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Abstract

The invention relates to the technical field of organic chemistry, in particular to a preparation method of glucal. 1-acetyl glucopyranosyl bromide is added in phosphate buffer solution which contains zinc powder and copper sulfate or the zinc powder and the 1-acetyl glucopyranosyl bromide are added in sodium dihydrogen phosphate water solution, stirring reaction is carried out for 0.5 to 8 hours under the room temperature, then NaOH or KOH is added, the stirring reaction is carried out again for 0.5 to 3 hours under the room temperature, after that, the glucal can be generated. The synthetic method of glucal is also called as a one-pot synthetic method of the glucal and has the advantages of simple operation, shortened process flow, high yield, short reaction time, low cost, less three wastes, small environmental pollution and easy industrialization.

Description

technical field [0001] The invention relates to the technical field of organic chemistry, in particular to a preparation method of glucal sugar. Background technique [0002] Glucal and acetylated glucal are very important raw materials in organic synthesis and pharmaceutical synthesis. At present, there are many methods for the preparation of acetylated glucal sugar, and more than a dozen kinds can be retrieved, and there are constantly new process reports. One of the main methods of preparing acetylated glucosylose and other glucosylose compounds is to obtain the target product from a substituent, such as: (1) Tetrahedron Letters2001, 42(42), 7371-7374 [0003] [0004] Another example: (2) Journal of the American Chemical Society 2005, 127(30), 10747-10752 [0005] [0006] Also as: (3) Synlett 2005, 4, 587-590 [0007] [0008] Another example (4) J.Org.Chem.1999, 64, 3987-3995 [0009] [0010] (5) Tetrahedron Letters 2006, 47(34), 6117-6120 [0011] ...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D309/30
Inventor 邵华武赵晋忠
Owner CHENGDU INST OF BIOLOGY CHINESE ACAD OF S
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