Looking for breakthrough ideas for innovation challenges? Try Patsnap Eureka!

Method for removing trichloroethyl of glucoside

A technology of trichloroethyl and trichloroethyl glycosides, applied in chemical instruments and methods, sugar derivatives, sugar derivatives, etc., can solve the problems of limited method expansion, narrow application scope, long reaction time, etc. The effect of wide range, short reaction time and low production cost

Inactive Publication Date: 2010-07-28
EAST CHINA NORMAL UNIVERSITY
View PDF0 Cites 0 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Some of the earliest removal methods such as Zn / AcOH (Lemieux, R.U., DriguezH., J.Am.Chem.Soc.1975, 97, 4069-4075), the method has a long reaction time during removal, and the solvent is an acid in the reaction , if there are acid-sensitive groups in some reactants, it is not suitable. At the same time, the acid solvent brings troubles to the post-processing, and a large amount of base must be used to neutralize the acid in the reaction, so the application of this system is limited.
And another Zn / NMI / EtOAc system (Somsak, L Czifrak, k.Veres.E., Tetrahedron Lett.2004, 45, 9095-9097), this method can be used for some groups containing acid-sensitive and easily reduced However, the removal of this method is only suitable for the removal of the trichloroethyl group in trichloroethyl saccharate, and the scope of application is relatively narrow, which also limits the expansion of the method

Method used

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
View more

Image

Smart Image Click on the blue labels to locate them in the text.
Viewing Examples
Smart Image
  • Method for removing trichloroethyl of glucoside
  • Method for removing trichloroethyl of glucoside
  • Method for removing trichloroethyl of glucoside

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0019] Take 2,2,2-trichloroethyl-β-O-tetraacetylglucoside 80mg (0.167mmol), Zn powder 87mg (1.338mmol) and NH 4 Cl 27mg (0.504mmol), sequentially added to 2ml of analytically pure ethanol, and then heated to reflux for trichloroethyl removal reaction, the heating temperature is 80°C, the reaction time is 5min, the reaction product is filtered and concentrated under reduced pressure Finally, 57.2 mg of 2,3,4,6-O-tetraacetylglucose was obtained, and the yield was 98.5%.

[0020] The product 2,3,4,6-O-tetraacetylglucose obtained from the above-mentioned examples is carried out 1 H-NMR analysis, the test data are as follows:

[0021] 1 H NMR (500MHz, CDCl 3 ): δ5.55(t, J=10Hz, 0.75H), 5.47(d, J=4Hz, 0.73H), 5.26(t, J=10Hz, 0.3H), 5.09(t, J=10Hz, 1H) , 4.86-4.92(m, 1H), 4.75(d, J=8Hz, 0.27H), 4.22-4.30(m, 2H), 4.12-4.18(m, 1.4H), 3.75(m, 0.3H), 2.00 -2.20 (4s, 12H).

Embodiment 2

[0023] Take 2,2,2-trichloroethyl-β-O-tetraacetylmannoside 80mg (0.167mmol), Zn powder 65mg (1.002mmol) and NH 4 Cl 27mg (0.504mmol), sequentially added to 5ml of analytically pure acetone, then heated to reflux for trichloroethyl removal reaction, the heating temperature was 60°C, the reaction time was 5min, the reaction product was filtered and concentrated under reduced pressure Finally, 56.9 mg of 2,3,4,6-O-tetraacetylmannose was obtained, and the yield was 90%.

[0024] The product 2,3,4,6-O-tetraacetylmannose obtained from the above-mentioned examples was carried out 1 H-NMR analysis, the test data are as follows:

[0025] 1 H NMR (500MHz, CDCl 3 ): δ5.47(dd, J=10, 3Hz, 1H), 5.29(m, 3H), 4.25(m, 2H), 4.14(d, J=10H, 1H), 2.0-2.18(4s, 12H) .

Embodiment 3

[0027] Take 2,2,2-trichloroethyl-β-O-tetrabenzylgalactoside 60mg (0.089mmol), Zn powder 46mg (0.714mmol) and NH 4 Cl 38.1mg (0.712mmol) was added to 2ml of analytically pure ethanol in sequence, and then heated to reflux for trichloroethyl removal reaction. The heating temperature was 50°C and the reaction time was 1.5h. The reaction product was filtered and reduced After concentrated under reduced pressure, 49.2 mg of 2,3,4,6-O-tetrabenzylgalactose was obtained, and the yield was 95.0%.

[0028] The product 2,3,4,6-O-tetrabenzylgalactose obtained from the above-mentioned examples is carried out 1 H-NMR analysis, the test data are as follows:

[0029] 1 HNMR (500MHz, CDCl 3 ): δ7.35(m, 30H), 5.28(t, 0.93H), 5.0~4.4(m, 12.3H), 415(t, 0.88H), 4.04(dd, 0.91H), 3.89(m, 1.45 H), 3.76(m, 0.55H), 3.6~3.5(m, 4H), 3.11(d, 0.5H).

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to View More

PUM

No PUM Login to View More

Abstract

The invention discloses a method for removing trichloroethyl of glucoside, which is characterized in that 2,2,2-trichloro-ethyl glycoside, Zn powder and ammonium chloride (NH4Cl) are dissolved in an organic solvent and are subject to the trichloroethyl removal reaction at the temperature of 15 to 120 DEG C, the molar volume ratio of the trichloro-ethyl glycoside, the Zn powder, the ammonium chloride (NH4Cl) and the organic solvent is 1mol:2 to 30 mol: 1 to 20 mol: 2 to 20 L, and the reaction product is filtered, decompressed and concentrated to obtain anomeric carbon-exposed sugar. Compared with the prior art, the trichloroethyl removal method has short reaction time, convenient post-treatment, high yield, wide application range, small toxicity of the raw material, environmental protection, economical performance and high efficiency, and has important significance on promoting the application of the -trichloro-ethyl glycoside in the carbohydrate chemistry and chemical engineering production.

Description

technical field [0001] The invention relates to the technical fields of medicine and fine chemical industry, in particular to a method for removing trichloroethyl groups from glycosides. Background technique [0002] Trichloroethyl glucoside as a synthetic building block can be used to synthesize some natural products (Lemieux, R.U., Driguez H., J.Am.Chem.Soc.1975, 97, 4069-4075), in some furanosides and pyranosides The application of trichloroethyl as a terminal protecting group is relatively common, but the removal of trichloroethyl as a protecting group is also very important. Some of the earliest removal methods such as Zn / AcOH (Lemieux, R.U., DriguezH., J.Am.Chem.Soc.1975, 97, 4069-4075), the method has a long reaction time during removal, and the solvent is an acid in the reaction , if there is an acid-sensitive group in some reactants, it is not suitable. At the same time, the acid solvent brings troubles to the post-processing, and a large amount of base must be use...

Claims

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to View More

Application Information

Patent Timeline
no application Login to View More
IPC IPC(8): C07H13/06C07H1/00
CPCY02P20/55
Inventor 张剑波王晓虎付杰
Owner EAST CHINA NORMAL UNIVERSITY
Features
  • Generate Ideas
  • Intellectual Property
  • Life Sciences
  • Materials
  • Tech Scout
Why Patsnap Eureka
  • Unparalleled Data Quality
  • Higher Quality Content
  • 60% Fewer Hallucinations
Social media
Patsnap Eureka Blog
Learn More

Browse by: Latest US Patents, China's latest patents, Technical Efficacy Thesaurus, Application Domain, Technology Topic, Popular Technical Reports.

© 2025 PatSnap. All rights reserved.Legal|Privacy policy|Modern Slavery Act Transparency Statement|Sitemap|About US| Contact US: help@patsnap.com