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

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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 ...

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.

Application Domain

Esterified saccharide compoundsSugar derivatives +2

Technology Topic

Organic solventState of art +11

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Examples

Experimental program(6)

Example Embodiment

[0018] Example 1

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

[0020] 2,3,4,6-O-tetraacetylglucose 1 H-NMR spectrum 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).

Example Embodiment

[0022] Example 2

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

[0024] The product 2,3,4,6-O-tetraacetyl mannose obtained in the above example 1 H-NMR spectrum analysis, the test data are as follows:

[0025] 1 H NMR(500MHz, CDCl 3 ): δ 5.47 (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) .

Example Embodiment

[0026] Example 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 turn, 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 pressure and concentration, 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 in the above examples 1 H-NMR spectrum 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 to 3.5 (m, 4H), 3.11 (d, 0.5H).

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Classification and recommendation of technical efficacy words

short reaction time
Simple process

Method for removing trichloroethyl of glucoside

AI-Extracted Technical Summary

Problems solved by technology

Abstract

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Examples

Example Embodiment

Example Embodiment

Example Embodiment

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Description & Claims & Application Information

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