Method of preparing 6-deoxy-L-talose

A technology for talose and rhamnose, which is applied in the field of synthesizing 6-deoxy-L-talose, can solve the problems of high price, cumbersome steps, few commercially available sources, etc., and achieves avoiding pollution, improving yield, simplifying Effects of compositing and post-processing steps

Inactive Publication Date: 2014-06-04
JIANGXI SCI & TECH NORMAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0003] 6-deoxy-L-talose mainly comes from biological extraction, and there are few commercial sources and the price is expensive
The steps of the above method are cumbersome, the yield is low, and it is difficult to be used for large-scale preparation

Method used

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  • Method of preparing 6-deoxy-L-talose

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0019] Step 1: Methyl-6-L-Rhamnose 2 Synthesis of: Dissolve L-rhamnose (40 g, 244 mmol) in methanol (400 mL), add H + Type cation exchange resin (40 g, 103 mmol) was stirred and refluxed for 12 h, then the resin was filtered off under reduced pressure, and the filtrate was concentrated to obtain 40 g of yellow oily glycoside-protected L-rhamnose, yield: 93%.

[0020] Step 2: Methyl-6-deoxy-2,3- O -Isopropylidene-6-L-rhamnoside 3 Synthesis of glycoside-protected L-rhamnose (40 g, 224.7 mmol) was dissolved in acetone (85 mL, 1123 mmol) and 2,2-dimethoxypropane (138 mL, 1123 mmol) mixed solution, Add p-toluenesulfonic acid (1.548 g, 9.0 mmol), and after stirring at room temperature for 2 h, wash with solid NaHCO 3 Neutralize p-toluenesulfonic acid until the pH of the system is greater than 7, remove the solvent under reduced pressure, and then separate by dry column chromatography (dichloromethane:methanol = 30:1) to obtain 47 g of a light yellow oily product, with a yield of ...

Embodiment 2

[0027] Step 1: Methyl-6-L-Rhamnose 2 Synthesis of: Dissolve L-rhamnose (40 g, 244 mmol) in methanol (400 mL), add H + Type cation exchange resin (40 g, 103 mmol) was stirred and refluxed for 12 h, then the resin was filtered off under reduced pressure, and the filtrate was concentrated to obtain 40 g of yellow oily glycoside-protected L-rhamnose, yield: 93%.

[0028] Step 2: Methyl-6-deoxy-2,3- O -Isopropylidene-6-L-rhamnoside 3 The synthesis of glycoside-protected L-rhamnose (20 g, 112.3 mmol) was dissolved in acetone (41 mL, 562 mmol) and 2,2-dimethoxypropane (69 mL, 562 mmol) mixed solution, Add concentrated sulfuric acid (650 μL, 12.2 mmol), stir at room temperature for 2 h, then wash with solid NaHCO 3 Neutralize p-toluenesulfonic acid until the pH of the system is greater than 7, remove the solvent under reduced pressure, and then separate by dry column chromatography (dichloromethane: methanol = 30:1) to obtain 23 g of a light yellow oily product, with a yield of 86%...

Embodiment 3

[0035] Step 1: Methyl-6-L-Rhamnose 2 Synthesis of: Dissolve L-rhamnose (40 g, 244 mmol) in methanol (400 mL), add H + Type cation exchange resin (40 g, 103 mmol) was stirred and refluxed for 12 h, then the resin was filtered off under reduced pressure, and the filtrate was concentrated to obtain 40 g of yellow oily glycoside-protected L-rhamnose, yield: 93%.

[0036] Step 2: Methyl-6-deoxy-2,3- O -Isopropylidene-6-L-rhamnoside 3 Synthesis of glycoside-protected L-rhamnose (40 g, 224.7 mmol) was dissolved in acetone (85 mL, 1123 mmol) and 2,2-dimethoxypropane (138 mL, 1123 mmol) mixed solution, Add p-toluenesulfonic acid (1.548 g, 9.0 mmol), and after stirring at room temperature for 2 h, wash with solid NaHCO 3 Neutralize p-toluenesulfonic acid until the pH of the system is greater than 7, remove the solvent under reduced pressure, and then separate by dry column chromatography (dichloromethane:methanol = 30:1) to obtain 47 g of a light yellow oily product, with a yield of ...

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Abstract

The invention belongs to the field of chemical synthesis. The invention relates to a method of synthesis of 6-deoxy-L-talose,including: 1) performing glucoside protection of 1-positon hydroxyl of L-rhamnose in methanol solution by utilizing cation exchange resin (732H+type) to obtain a compound; 2) performing isopropylidene protection of hydroxyls at 2 and 3 positions of the compound to obtain a compound; 3) oxidizing 4-position hydroxyl of the compound to a ketone carbonyl group by utilizing a Swern oxidation system, so as to obtain a compound; 4) performing stereoselective reduction of 4-position carbonyl of the compound by utilizing sodium borohydride or sodium cyanoborohydride, so as to obtain a precursor compound with an opposite configuration to the raw materials, of 6-deoxy-L-talose; 5) refluxing the compound in sulfuric acid aqueous solution to hydrolyze to obtain 6-deoxy-L-talose. The preparing method using easily-available L-rhamnose having low price as the initial raw material, is a simple method, and is utility and efficient.

Description

technical field [0001] The invention relates to a method for synthesizing 6-deoxy-L-talose by using L-rhamnose as a raw material. Background technique [0002] 6-deoxy-L-talose is a relatively rare 6-deoxypyranose, which mainly exists in a few bacteria and plants. For example, in mycobacteria ( Mycobacterium aviam and Mycobacterium materianum ), sugar esters of Pseudomonas ( Pseudomonas psaudomalle ), Citrobacter ( Citrobacter ) lipopolysaccharide and Actinomyces bovis ( Actinomyces bovis ) were found in the cell walls of 6-deoxy-L-talose. 6-deoxy-L-talose is an important reducing sugar, which has great significance in many frontier fields of biology and medicine, such as biochemistry, molecular biology, genetics, immunology, oncology, cell engineering, etc. Value. In addition, the acetyl-protected 6-deoxy-L-talose precursor is also an important fragment for the synthesis of glycopeptides and oligosaccharides containing 6-deoxy-L-talose. [0003] 6-deoxy-L-talose...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07H1/00C07H3/08C07H13/06
CPCY02P20/55
Inventor 孙麒龚珊珊王强杨庆昆
Owner JIANGXI SCI & TECH NORMAL UNIV
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