Preparation method of 2,3,4,6-tetra-oxo-benzyl-d-galactopyranose
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A technology of galactopyranose and benzothiazolylthiotetrabenzyl half, applied in the field of preparation of 2,3,4,6-tetra-oxo-benzyl-D-galactopyranose, which can solve the cost High yield, low yield and other problems, to achieve the effect of simple operation, easy access to raw materials, saving operating costs and materials
Active Publication Date: 2016-08-17
济南尚博医药股份有限公司
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[0004] In order to solve the high cost and low yield in the preparation of 2,3,4,6-tetra-oxygen-benzyl-D-pyranose (type) galactose in the above prior art, the present invention provides A preparation method of 2,3,4,6-tetra-oxo-benzyl-D-galactopyranose with three-step reaction, simple operation and readily available raw materials
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Embodiment 1
[0023] Example 1 5.5 : 2 : 1: 1.1
[0024] a) Add 5.5mol acetic anhydride and 2mol zinc chloride at room temperature, add 1mol galactose in 8 batches at 10-15°C, after the reaction is complete, add 1.1mol 2-mercaptobenzothiazole and heat to 50-60°C; Workup afforded 0.87 mol of benzothiazolylthioacetylgalactose.
[0025] 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.
[0026] c) Add 0.79 mol of benzothiazolylthiotetrabenzyl galactose 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, and the reaction is completed After post-treatment, 0.71mol 2,3,4,6-tetra-oxo-benzyl-D-galactopyranose was obtained with a yield of 71%.
[0027] The post-treatment i...
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Abstract
The invention relates to the field of saccharide compounds, particularly a method for preparing 2,3,4,6-tetra-oxy-benzyl-D-galactopyranose. The method comprises the following steps: preparing benzothiazolyl thioacetyl galactose from galactose under the actions of acetic anhydride and a catalyst 2-mercaptobenzothiazole; preparing benzothiazolyl thiotetrabenzyl galactose from the benzothiazolyl thioacetyl galactose under the actions of potassium hydroxide and benzyl chloride; and preparing the 2,3,4,6-tetra-oxy-benzyl-D-galactopyranose from the benzothiazolyl thiotetrabenzyl galactose under the action of N-bromosuccinimide. The method synthesizes the 2,3,4,6-tetra-oxy-benzyl-D-galactopyranose by a three-step reaction process, and effectively enhances the purity and yield of the product; and the method is simple to operate and accessible in raw materials, and saves the operating cost and materials.
Description
technical field [0001] The invention relates to the field of sugar compounds, in particular to a preparation method of 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. [0003] 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 Mild and EfficientChemoselective Deprotection of Anomeric O-Methyl Glycosides with TritylTetrafluoroborate, Journal of Organic Chemistry, 2008, vol. 73, # 15 p.5993-5995, the above-mentioned method catalyst triphenyltetrafluoroborate carbon is relatively expensive, and the cost is too high, Or use galactose for acetylation, and then prepare p-tol...
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