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A method for preparing 2,3,4,6-tetra-oxo-benzyl-d-galactopyranose

A kind of technology of galactopyranose and benzothiazolylthiotetrabenzyl half, applied in the field of preparation of 2,3,4,6-tetra-oxo-benzyl-D-galactopyranose, can solve the problem of yield Low cost, high cost, etc., to achieve the effect of easy to obtain raw materials, simple operation, saving operating costs and materials

Active Publication Date: 2016-04-27
济南尚博医药股份有限公司
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  • Application Information

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Problems solved by technology

[0005] In order to solve the high cost and low yield in the preparation of 2,3,4,6-tetra-oxo-benzyl-D-pyranose (type) galactose in the above prior art, the present invention provides A method for preparing 2,3,4,6-tetra-oxo-benzyl-D-galactopyranose using three-step reaction, simple operation and readily available raw materials

Method used

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  • A method for preparing 2,3,4,6-tetra-oxo-benzyl-d-galactopyranose
  • A method for preparing 2,3,4,6-tetra-oxo-benzyl-d-galactopyranose

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Embodiment 15

[0025] Example 15.5:2:1:1.1

[0026] a) Add 5.5mol acetic anhydride and 2mol zinc chloride at room temperature, add 1mol galactose in 10 batches at 10-15°C, after the reaction is complete, add 1.1mol 2-mercaptobenzothiazole, heat to 50-60°C; after post-treatment 0.87 mol of benzothiazolylthioacetylgalactose was obtained.

[0027] b) Add 3.48 mol of potassium hydroxide and 0.87 mol of benzothiazolyl thioacetylgalactose to 8.7 mol of benzyl chloride and heat to reflux. After the reaction is completed, the temperature is lowered, and 0.79 mol of benzothiazolyl thiogalactose is obtained after post-treatment. Benzylgalactose.

[0028] c) Add 0.79 mol of benzothiazolylthiotetrabenzylgalactose to 4 mol of acetone to dissolve, add 2 mol of water, stir at room temperature, add 0.87 mol of N-bromosuccinimide, stir for 0.5 hours, after the reaction is completed The treatment yielded 0.71mol 2,3,4,6-tetra-oxo-benzyl-D-galactopyranose with a yield of 71%.

[0029] The post-treatment in ...

Embodiment 26

[0032] Example 26:2:1:1.2

[0033] a) Add 6mol acetic anhydride and 2mol zinc chloride at room temperature, add 1mol galactose in 10 batches at 10-15°C, add 1.2mol 2-mercaptobenzothiazole after the reaction is completed, and heat to 50-60°C; 0.88 mol benzothiazolylthioacetylgalactose.

[0034] b) Add 3.6 mol of potassium hydroxide and 0.88 mol of benzothiazolyl thioacetylgalactose to 9.2 mol of benzyl chloride and heat to reflux. After the reaction is completed, the temperature is lowered, and 0.81 mol of benzothiazolyl thiogalactose is obtained after post-treatment. Benzylgalactose.

[0035] c) Add 0.81 mol of benzothiazolylthiotetrabenzylgalactose to 4 mol of acetone to dissolve, add 2 mol of water, stir, add 0.94 mol of N-bromosuccinimide at room temperature, stir for 0.5 hours, after the reaction is completed The treatment yielded 0.72mol 2,3,4,6-tetra-oxo-benzyl-D-galactopyranose with a yield of 72%.

[0036] The post-treatment in step a is to add dropwise 10mol of wat...

Embodiment 36

[0039] Example 36.5:2:1:1.2

[0040] a) Add 65mol acetic anhydride and 20mol aluminum chloride at room temperature, add 10mol galactose in 10 batches at 10-15°C, add 12mol 2-mercaptobenzothiazole after the reaction is completed, and heat to 50-60°C; after post-treatment, 8.9 mol benzothiazolylthioacetylgalactose.

[0041] b) Add 44.5 mol of potassium hydroxide and 8.9 mol of benzothiazolyl thioacetylgalactose to 106.8 mol of benzyl chloride and heat to reflux. After the reaction is completed, the temperature is lowered, and 8.25 mol of benzothiazolyl thiogalactose is obtained after post-treatment. Benzylgalactose.

[0042]c) Add 8.25 mol of benzothiazolylthiotetrabenzylgalactose to 40 mol of acetone to dissolve, add 20 mol of water, stir at room temperature, add 9.6 mol of N-bromosuccinimide, stir for 0.5 hours, after the reaction is completed The treatment yielded 7.33mol2,3,4,6-tetra-oxo-benzyl-D-galactopyranose with a yield of 73.3%.

[0043] The post-treatment in step a...

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Abstract

The invention relates to the field of sugar compounds and in particular relates to a method for preparing 2,3,4,6-tetra-O-benzyl -D-galactose. The method comprises the steps of preparing benzothiazolylthioacetyl galactose from galactose in the presence of acetic anhydride, catalysts and 2-mercaptobenzothiazole, preparing benzothiazolylthiotetrabenzyl galactose from benzothiazolylthioacetyl galactose in the presence of potassium hydroxide and benzyl chloride, and preparing 2,3,4,6-tetra-O-benzyl -D-galactose from benzothiazolylthiotetrabenzyl galactose in the presence of N-bromosuccinimide. The method has the beneficial effects that 2,3,4,6-tetra-O-benzyl -D-galactose is synthesized by a three-step reaction method, so that the purity and yield of the product are effectively increased; the method is simple to operate; the raw materials are accessible; the operating cost and the materials are saved.

Description

technical field [0001] The invention relates to the field of sugar compounds, in particular to a method for preparing 2,3,4,6-tetra-oxo-benzyl-D-galactopyranose. Background technique [0002] 2,3,4,6-tetra-oxo-benzyl-D-galactopyranose, also known as 2,3,4,6-tetra-O-benzyl-D-galactopyranoside, English name: 2,3,4,6-Tetra-O-benzyl-D-galactose, CAS number: 53081-25-7, molecular formula: C34H36O6, the structural formula is as follows: [0003] [0004] In the prior art, galactosyl glycoside is generally prepared by using galactose and methanol, and then tetrabenzyl galactose is prepared from galactosyl glycoside, and then demethylated by triphenyltetrafluoroborate carbon. Such as MildandEfficientChemoselectiveDeprotectionofAnomericO-MethylGlycosideswithTritylTetrafluoroborate, JournalofOrganicChemistry, 2008, vol.73, #15p.5993-5995, the above method catalyst triphenyltetrafluoroborate carbon is relatively expensive, the cost is too high, or use galactose for acetylation, and...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07H15/18C07H1/00
Inventor 孟庆文孔令华张恩选赵海峰张雷索晨苏
Owner 济南尚博医药股份有限公司
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