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Method for preparing glycal

A technology of vinyl sugar and benzoylated vinyl sugar, which is applied in the direction of organic chemistry, can solve the problems of cumbersome operation, high cost, and low yield, and achieve the effect of short process flow, low cost and fast response

Inactive Publication Date: 2010-06-23
CHENGDU INST OF BIOLOGY CHINESE ACAD OF S
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  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0011] The purpose of the present invention is to solve the shortcomings of high cost, cumbersome operation and low yield in the preparation method of vinyl sugar. We provide a method for synthesizing vinyl sugar with cheap raw materials, high yield, energy saving and environmental protection, and simple and effective

Method used

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  • Method for preparing glycal
  • Method for preparing glycal
  • Method for preparing glycal

Examples

Experimental program
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Effect test

example 1

[0018] Example 1: Add 100mg of acetylated glucosinolate bromide, 0.5mL PEG-600 and 0.5mL H2O to a 25mL round bottom flask, add 32mg of zinc powder, stir and react at room temperature for 20 minutes, after TLC detects that the reaction is complete, purify by silica gel column , to obtain 58 mg of pure acetylated glucal sugar, with a yield of 88%.

example 2

[0019] Example 2: Add 100mg acetylated glucosinolate bromide, 0.5mL PEG-400 and 0.5mL H2O to a 25mL round bottom flask, add 32mg zinc powder, stir and react at room temperature for 20 minutes, after the reaction is complete by TLC, purify by silica gel column , to obtain 55 mg of pure acetylated glucal, with a yield of 83%.

example 3

[0020] Example 3: Add 100mg of acetylated glucosinolate bromide, 0.5mL PEG-2000 and 0.5mL H2O to a 25mL round bottom flask, add 32mg of zinc powder, stir and react at room temperature for 20 minutes, after TLC detects that the reaction is complete, purify by silica gel column , to obtain 57 mg of pure acetylated glucal sugar, with a yield of 86%.

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Abstract

The invention belongs to the technical field of organic chemistry, and particularly relates to a method for preparing acetylated glycal, acetylated disaccharide glycal and benzoylated glycal. Acetylated glycosyl bromide or acetylated disaccharide bromide or benzoylated glycosyl bromide is added into a system of PEG and water, and then Zn powder is added to carry out room temperature reaction to respectively generate the acetylated glycal or the acetylated disaccharide glycal or the benzoylated glycal. The invention has the advantages of simple operation, short process, high yield, fast reaction, low cost, fewer three wastes, energy saving, environment protection, easy industrialization and the like.

Description

technical field [0001] The invention belongs to the technical field of organic chemistry, and in particular relates to a preparation method of acetylated vinyl sugar, acetylated disaccharide vinyl sugar and benzoylated vinyl sugar. Background technique [0002] In organic synthesis and pharmaceutical synthesis, acetylated glycosides, acetylated diglucosides and benzoylated glycosides are synthetically active natural products, O-glycosides, C-glycosides, N-glycosides and S-glycosides and other compounds important raw materials. At present, there are many methods for the preparation of acetylated vinyl sugars, and more than a dozen kinds can be retrieved, and there are new process reports; few. The main method of preparing enose is to obtain the target product from the substituted sugar at the 1-position through elimination reaction, such as: (1) J.Am.Chem.Soc., 2005, 127(30), 10747-10752. [0003] [0004] Another example: (2) Synlett, 2005, 4, 587-590. [0005] [...

Claims

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Application Information

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IPC IPC(8): C07D309/30
Inventor 邵华武赵晋忠魏善巧
Owner CHENGDU INST OF BIOLOGY CHINESE ACAD OF S
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