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Deoxysugar and preparation method of the deoxysugar

A technology for deoxysugar and dideoxypyranose, which is applied in the preparation of sugar derivatives, deoxy/unsaturated sugars, chemical instruments and methods, etc., can solve separation and extraction difficulties, low deoxysugar content, and high monosaccharide price. The problem is to overcome the difficulty of separation and extraction, the separation is simple, and the reaction conditions are easy to control.

Inactive Publication Date: 2012-07-25
FUDAN UNIV
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  • Summary
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  • Claims
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Problems solved by technology

Among them, the special biological effects of deoxysugars have attracted more and more people's attention, but the content of deoxysugars in nature is relatively small, and separation and extraction are difficult. The current chemical synthesis methods such as ring-closing conversion synthesis, two-step The synthesis method, Izumoring synthesis method, etc. are also often very complicated and have limitations and other defects, resulting in expensive monosaccharides used as synthetic raw materials

Method used

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  • Deoxysugar and preparation method of the deoxysugar
  • Deoxysugar and preparation method of the deoxysugar

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0017] Example 1 Synthesis of Intermediate 5 or 6:

[0018] Dissolve D-galactose or D-glucose (1.0 eq.), benzaldehyde dimethyl acetal (1.0-10.0 eq.) in an aprotic organic solvent, add protic acid or Lewis acid (0.01-2.0 eq.) , control the temperature at -40 to 80 oC to react; after the reaction is completed, add an appropriate amount of base to quench the reaction; the reaction solution is concentrated, and the residue is subjected to silica gel column chromatography to obtain a white solid, and intermediate 5 or 6 (4,6-O- Benzylidene-2-deoxygalactoside 5 or 4,6-O-benzylidene-2-deoxyglucoside 6).

[0019] Due to different conditions, the yield of intermediate 5 or 6 is 20-87%.

Embodiment 2

[0020] Example 2 Synthesis of Intermediate 7 or 8:

[0021] The intermediate 5 or 6 (1.0 eq.) was dissolved in carbon tetrachloride, respectively, and bromosuccinimide (NBS, 1.0-2.0 eq.), azobisisobutyronitrile (AIBN, 0.01-0.1 eq.), barium carbonate (0.1-1.0 eq.); reacted at 40-70 oC for 2-10 hours; after the reaction was completed, the solvent was evaporated, and the silica gel column chromatography gave a colorless transparent liquid, and intermediate 7 or 8.

[0022] The yield of intermediate 7 is 68%, and the yield of intermediate 8 is 65%.

Embodiment 3

[0023] Example 3 Synthesis of Intermediate 9 or 10:

[0024] Dissolve the intermediate 7 or 8 (1.0 eq.) in dry tetrahydrofuran respectively, add lithium aluminum hydride (1.0-10.0 eq.) in batches, until no bubbles are generated, add 1mol / L hydrochloric acid; The solution was concentrated after filtration, and the residue was subjected to silica gel column chromatography to obtain a colorless transparent liquid, and intermediate 9 or 10 (2,6-dideoxygalactoside 9 or 2,6-dideoxyglucoside 10) was obtained.

[0025] The yield of intermediate 9 was 83%, and the yield of intermediate 10 was 81%.

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Abstract

The invention belongs to the field of pharmacy and particularly relates to deoxysugar and a preparation method of the deoxysugar, in particular to 2, 6- or 2, 3-di-deoxy pyranose and the preparation method of the 2, 6- or 2, 3-di-deoxy pyranose. The 2, 6- or 2, 3-di-deoxy pyranose uses galactose olefin or glucose olefin as a raw material to perform simple and efficient reaction to obtain four 2, 6- or 2, 3-di-deoxy pyranoses. According to the preparation method of the 2,6- or 2,3-di-deoxy pyranose, the process is concise, the condition is easy to control, the yield is high, and separation is simple.

Description

technical field [0001] The invention belongs to the field of pharmacy, and relates to rare sugar and its preparation method, in particular to deoxy sugar and its preparation method, especially to deoxy sugar 2,6- or 2,3-dideoxypyranose and its preparation method. Background technique [0002] Rare sugars are compounds in which at least one hydroxyl group in common sugar molecules is replaced by hydrogen atoms or other groups. They are widely found in natural products and play important physiological functions in the fields of diet, health care, and medicine, especially in many Among the well-known drug molecules, it plays an irreplaceable biological role in the compound structure. Among them, the special biological effects of deoxysugars have attracted more and more people's attention, but the content of deoxysugars in nature is relatively small, and separation and extraction are difficult. The current chemical synthesis methods such as ring-closing conversion synthesis, two...

Claims

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Application Information

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IPC IPC(8): C07H3/08C07H1/00
Inventor 丁宁李英霞张伟
Owner FUDAN UNIV
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