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Method for preparing sugar ortho ester

A technology of sugar orthoester and monosaccharide, applied in the field of preparation of sugar orthoester, can solve the problems of large environmental pollution and high cost

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

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Problems solved by technology

[0018] The purpose of the present invention is to solve the shortcomings of large environmental pollution and high cost in the preparation method of sugar ortho ester. We provide a simple and effective synthetic sugar ortho ester with low pollution, cheap raw materials, fast reaction speed, high yield Methods

Method used

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  • Method for preparing sugar ortho ester
  • Method for preparing sugar ortho ester
  • Method for preparing sugar ortho ester

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0025] Example 1: Add 57mg 2,3,4,6-tetra-O-acetylbromoglucopyranose and 0.57mL acetonitrile to a 10mL round bottom flask, then add 45mg tetrabutylammonium bromide, 46mg sodium bicarbonate , 0.056mL methanol and 57mg Molecular sieves, stirred at 40°C for 3 hours. After the reaction was detected by TLC, it was directly concentrated under reduced pressure and purified by silica gel column chromatography (eluent: petroleum ether / ethyl acetate 3:2) to obtain pure 3,4,6-tri-O-acetylpyran Glucose-1,2-(methyl orthoester) 43 mg, yield 86%.

Embodiment 2

[0026] Example 2: Add 57mg 2,3,4,6-tetra-O-acetylbromoglucopyranose and 0.57mL acetonitrile to a 10mL round bottom flask, then add 45mg tetrabutylammonium bromide, 23mg sodium bicarbonate , 0.056mL methanol and 57mg Molecular sieves, stirred at 40°C for 6 hours. After the reaction was detected by TLC, it was directly concentrated under reduced pressure and purified by silica gel column chromatography (eluent: petroleum ether / ethyl acetate 3:2) to obtain pure 3,4,6-tri-O-acetylpyran Glucose-1,2-(methyl orthoester) 42 mg, yield 84%.

Embodiment 3

[0027] Example 3: Add 57mg 2,3,4,6-tetra-O-acetylbromoglucopyranose and 0.57mL acetonitrile to a 10mL round bottom flask, then add 13mg tetrabutylammonium bromide, 23mg sodium bicarbonate , 0.056mL methanol and 57mg Molecular sieves, stirred at 40°C for 6 hours. After the reaction was detected by TLC, it was directly concentrated under reduced pressure and purified by silica gel column chromatography (eluent: petroleum ether / ethyl acetate 3:2) to obtain pure 3,4,6-tri-O-acetylpyran Glucose-1,2-(methyl orthoester) 40 mg, yield 80%.

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Abstract

The invention belongs to the technical field of organic chemistry, in particular to a method for preparing sugar ortho ester. The method comprises the following steps: adding acetyl or benzoyl glycosyl bromide to a system containing alcohol or monosaccharide, sodium bicarbonate, tetrabutyl ammonium bromide, and acetonitrile or dichloromethane containing, stirring the mixture for reaction, and finally generating the sugar ortho ester. The method has the advantages of easy operation, little environmental pollution, high yield, low cost, 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 sugar ortho ester. Background technique [0002] Orthoester is a very important intermediate in organic synthesis. In carbohydrate synthesis, 1,2-orthoester is widely used in the synthesis of oligosaccharides as a sugar donor. At present, the existing many reports of the preparation method of ortho ester, wherein the most widely used method is to use tetrabutylammonium bromide / tetrabutylammonium iodide, organic base [s-collidine, 2,6-lutidine, Et 3 N, (MeO) 2 CHNMe 2 ] as a catalyst. Such as: [0003] (1) Tetrahedron, 2002, 58, 7345. [0004] [0005] (2) Journal of Organic Chemistry, 1994, 59, 6728. [0006] [0007] (3) Journal of Natural Products, 2001, 64(9), 1210. [0008] [0009] Another method is to use silver salt (Ag 2 SO 4 、Ag 2 CO 3 、Ag 2 O, etc.) and organic bases [s-collidine, EtN(Pr-i) 2 ] as a ca...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07H13/02C07H9/04B01J29/06
Inventor 邵华武魏善巧赵晋忠
Owner CHENGDU INST OF BIOLOGY CHINESE ACAD OF S
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