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Method for ultrasonically synthesizing glycal

A technology of ultrasonic wave and alkenose, applied in the fields of medicinal chemistry and organic synthesis, can solve the problems of separation and purification, low yield, high cost, complicated intermediate product processing, etc., and achieves the effect of reducing cost and thorough reaction.

Inactive Publication Date: 2011-01-05
SHANXI AGRI UNIV
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  • Abstract
  • Description
  • Claims
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AI Technical Summary

Problems solved by technology

[0014] In order to solve the shortcomings of high cost, cumbersome intermediate product treatment, separation and purification and low yield in the preparation method of alkenyl sugar, we provide a simple and rapid ultrasonic synthesis of acetylated grape with cheap raw materials and no need for separation and purification of intermediate products. Method for ultrasonically synthesizing alkenose and or acetylated maltose

Method used

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  • Method for ultrasonically synthesizing glycal
  • Method for ultrasonically synthesizing glycal
  • Method for ultrasonically synthesizing glycal

Examples

Experimental program
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Embodiment 1

[0028] Example 1: 10 g of glucose, 100 mL of acetic acid, 32.5 mL of acetic anhydride, 0.5 g of p-toluenesulfonic acid were added to a 500 mL round bottom flask, and ultrasonic reaction was performed for 10 minutes, and 12.5 mL of acetyl bromide, methanol 9.0 mL, ultrasonic oscillation, power 420W (model DST20500) and react for 1 hour. TLC detected that the reaction was complete, diluted with dichloromethane, washed with water, and recrystallized with ethanol to obtain 21.9 g of bromoglucose crystals with a yield of 96%.

[0029] Add 44 g of β-cyclodextrin, 220 mL of water and 11 g of zinc powder to the above-mentioned bromosugar, ultrasonic power 480W, (model DST20500) shake for 10 minutes, add ethyl acetate to dilute, filter, and the filtrate is washed with ethyl acetate Extracted 3 times, combined the organic phases, dried with anhydrous sodium sulfate, filtered, and concentrated under reduced pressure to obtain crude acetylated glucal, and then recrystallized with ethyl ace...

example 2

[0030] Example 2: Add 10 g of glucose, 100 mL of acetic acid, 32.5 mL of acetic anhydride, 5 drops of perchloric acid in a 500 mL round bottom flask, and ultrasonically react for 5 minutes. Add 12.5 mL of acetyl bromide and 9.0 mL of methanol to the above reaction solution, and ultrasonically (Power 450W, Model DST20500) Shake and react for 1 hour, TLC detects that the reaction is complete, dilute with dichloromethane, wash with water, and recrystallize with ethanol to obtain 21.0 g of bromosugar crystals.

[0031]Add 42 g of β-cyclodextrin, 210 mL of water and 11 g of zinc powder to the above-mentioned bromosugar, ultrasonic power 450W, (model DST20500) shake and react for 20 minutes, add ethyl acetate to dilute, filter, and the filtrate is washed with ethyl acetate Extracted 3 times, combined the organic phases, dried with anhydrous sodium sulfate, filtered, and concentrated under reduced pressure to obtain crude acetylated glucal, and then recrystallized with ethyl acetate a...

example 3

[0032] Example 3: Add 10 g of maltose, 100 mL of acetic acid, 32.5 mL of acetic anhydride, 0.5 g of p-toluenesulfonic acid into a 500 mL round bottom flask, and ultrasonically react for 20 minutes. Add 7.5 mL of acetyl bromide and 4.5 mL of methanol to the above reaction solution mL, ultrasonic power 420W, (model DST20500) shaking reaction for 1.5 hours, TLC detection of complete reaction, diluted with dichloromethane, washed with water, and recrystallized with ethanol to obtain 19.4 g of bromomaltose crystals, with a yield of 95%.

[0033] Add 40 g of β-cyclodextrin, 200 mL of water and 6 g of zinc powder to the above bromosugar, ultrasonic power 450W, (model DST20500) shake reaction for 1 hour, add ethyl acetate to dilute, filter, and the filtrate is washed with ethyl acetate Extract 3 times, combine the organic phases, add anhydrous sodium sulfate to dry, filter, and concentrate under reduced pressure to obtain crude acetylated glucal, and then recrystallize with ethyl aceta...

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Abstract

The invention relates to pharmaceutical chemistry and organic synthesis technology, in particular to a method for ultrasonically synthesizing glycal, such as acetylated glucal or acetylated maltose, and solves the problems of high cost, complex intermediate product processing, need of separation and purification, low yield and the like in the glycal preparation method. The method comprises the following steps of: preparing D-acetylated glucose or D-acetylated maltose from D-glucose and / or D-maltose and acetic anhydride under the catalytic action of perchloric acid or benzene sulfonic acid; directly adding the produced D-acetylated glucose or D-acetylated maltose into acetyl bromide and methanol to obtain 1-bromoacetylglucose and / or 1-bromoacetylmalcose; adding the obtained bromoacetylglucose or bromoacetylmalcose into aqueous solution of beta-cyclodextrin; adding zinc powder into the solution; and performing ultrasonic oscillation reaction to obtain the D-acetylated glucal and / or D-acetylated maltose. The method has the advantages of reducing the cost, along with complete reaction and yield of over 90 percent.

Description

[0001] technical field [0002] The invention relates to medicinal chemistry and organic synthesis technology, in particular to a method for synthesizing acetylated glucuronose and acetylated maltoselenose by ultrasonic waves. Background technique [0003] In organic synthesis and pharmaceutical synthesis, monosaccharides and disaccharides are synthetically active natural products, O -glycosides, C -glycosides, N -glycosides, S -An important raw material for compounds such as glycosides. At present, there are many methods for the preparation of acetylated vinyl sugars, and more than a dozen kinds can be retrieved, and new technology reports are constantly being reported; but there are few reports on diglucosyl sugars. The main method of preparing acetylated glucal sugar is to obtain the target from a substituent, such as: (1) Synlett , 628-630, 1996 [0004] [0005] Another example: (2) Journal of the American Chemical Society , 127(30) , 10747-10752, 2005...

Claims

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Application Information

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IPC IPC(8): C07D309/30C07H17/04C07H1/00
Inventor 赵晋忠邵华武杨万明白向东宁乃瑞
Owner SHANXI AGRI UNIV
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