Method for removing trichloroethyl of glucoside

A technology of trichloroethyl and trichloroethyl glucoside, which is applied in the direction of chemical instruments and methods, sugar derivatives, sugar derivatives, etc., can solve the problems of narrow application range, troublesome post-processing, long reaction time, etc., and achieve reaction The effect of short time, convenient post-processing and low production cost

Inactive Publication Date: 2013-03-13
EAST CHINA NORMAL UNIV
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Problems solved by technology

Some of the earliest removal methods such as Zn / AcOH (Lemieux, R.U., Driguez H., J. Am. Chem. Soc. 1975, 97, 4069-4075), which reacted The time is long, the solvent in the reaction is an acid, and it is not suitable if there are acid-sensitive groups in some reactants. At the same time, the acid solvent brings troubles to the post-processing. application of the system
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 Acid-sensitive and easily reduced group substrates, but the removal of this method is only suitable for the removal of trichloroethyl in trichloroethyl saccharate, and the scope of application is relatively narrow, which also limits the expansion of the method

Method used

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  • 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 (1.338 mmol) 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 (1.002 mmol) 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 is 60 ° C, the reaction time is 5min, the reaction product is 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 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 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).

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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 can be used as a synthetic building block 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 more 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., Driguez H., J. Am. Chem. Soc. 1975 , 97, 4069-4075), this method takes a long time to remove, and the solvent in the reaction is an acid, and it is not suitable if there are acid-sensitive groups in some reactants, and the acid solvent brings troubles to the post-treatment , have to use a large amount of alkali to neutralize th...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07H13/06C07H1/00
CPCY02P20/55
Inventor 张剑波王晓虎付杰
Owner EAST CHINA NORMAL UNIV
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