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Novel type sugar of C12 high carbon, its derivative, preparation method and application

A sugar derivative, C12 technology, applied in the field of sugar compounds and their preparation, can solve the problems of less high aldose, no synthetic high carbon ketose, etc., and achieves mild conditions, good market prospects, and high reaction yield. Effect

Inactive Publication Date: 2006-10-11
KAIFENG PHARMA GRP
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  • Abstract
  • Description
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AI Technical Summary

Problems solved by technology

At present, there are relatively many reports on the synthesis methods of carboglycoside disaccharides and high dialdehyde sugars (especially carboglycoside disaccharides), fewer reports on high carbon ketoses, and no reports on the synthesis of high carbon ketoses

Method used

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  • Novel type sugar of C12 high carbon, its derivative, preparation method and application
  • Novel type sugar of C12 high carbon, its derivative, preparation method and application
  • Novel type sugar of C12 high carbon, its derivative, preparation method and application

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0032] Example 1 Preparation C 12 high carbon ketose

[0033] 1,4:3,6-Fruitose (1.44g, 10mmol) was dissolved in methanol (10mL), a catalytic amount of sodium methoxide was added, and the mixture was refluxed for 6 hours. After the reaction, the reaction solution was concentrated, crystallized from absolute ethanol, and C was obtained. 12 High carbon ketose 1.15g, yield 80%. C 12 The data of the high-carbon ketose experiment are as follows.

[0034] C 12 h 16 o 8 , mp 190-191°C, [α] D 20 =+173.4(c 1.10, CH 3 OH); υ=3381,1771,1401,1128,1066,880,747cm -1 ; 1 HNMR (400MHz, DMSO-d 6 ): δ4.87(dd, J=4.8, 6.8Hz, 1H), 4.39-4.41(m, 2H), 4.26(d, J=6.8Hz, 1H), 4.10-4.15(m, 2H), 3.92( s, 1H), 3.95(d, J=8.8Hz, 1H), 3.82(dd, J=4.8, 8.8Hz, 1H), 3.79(m, 1H), 3.54(dd, J=4.8, 8.8Hz, 1H ), 3.42(d, J=8.8Hz, 1H), 3.38(m, 1H); 13 CNMR (100MHz, DMSO-d 6): δ212.8, 83.2, 81.4, 81.0, 80.3, 79.7, 78.4, 72.5, 72.3, 72.2, 71.8, 71.3.

Embodiment 2

[0035] Example 2 Preparation of Derivatives When X=O Shown in General Formula 1

[0036] The above prepared C 12 High carbon sugar (1.44g, 5mmol) was dissolved in ethanol (20mL), 0.5mL of nitromethane and 20mg of potassium fluoride were added, and reacted at 80°C for 5 hours. After the reaction was completed, the reaction solution was concentrated and recrystallized from methanol to obtain 1.66 g of the derivative represented by general formula 1 when X=O, with a yield of 95%. The experimental data are as follows.

[0037] C 13 h 19 NO 10 , mp 160-162°C, [α] D 20 =+92.9 (c=1.06, CH 3 OH), υ=3405, 2942, 2849, 1554, 1416, 1123, 1075, 859, 702cm -1 ; 1 HNMR (400MHz, D 2 O): δ4.95(d, J=13.6Hz, 1H), 4.85(d, J=13.6Hz, 1H), 4.60(t, J=4.0Hz, 1H), 4.59(d, J=5.4Hz, 1H), 4.48(d, J=4.0Hz, 1H), 4.31(m, 1H), 4.26(t, J=5.4Hz, 1H), 4.17(m, 1H), 3.91(s, 2H), 3.89( dd, J=6.4, 8.8Hz, 1H), 3.86(dd, J=6.8, 8.8Hz, 1H), 3.78(s, 1H), 3.50(t, J=8.8Hz, 1H), 3.45(t, J = 8.8Hz, 1H); 13 CNMR...

Embodiment 3

[0038] Example 3 Preparation of Derivatives When X=H Shown in General Formula 1

[0039] The product obtained in Example 2 (1.05 g, 3 mmol) was dissolved in methanol (120 mL), a catalyst 10% Pd / C (105 mg) was added, and hydrogenation was performed at 40° C. for 8 hours. After the reaction was completed, the reaction liquid was concentrated and crystallized from acetonitrile to obtain 852 mg of the derivative represented by general formula 1 when X=H, with a yield of 89%. The experimental data are as follows.

[0040] C 13 h 21 NO 8 , mp 76-78°C, [α] D 20 =+86.5 (c=0.32, CH 3 OH), υ=3367, 2946, 2872, 1131, 1082, 1042, 866cm -1 ; 1 HNMR (400MHz, D 2 O): δ4.66(d, J=4.4Hz, 1H), 4.65(t, J=4.4Hz, 1H), 4.32(m, 1H), 4.31(t, J=4.4Hz, 1H), 4.28( d, J=4.4Hz, 1H), 4.24(m, 1H), 3.95(s, 2H), 3.94(m, 1H), 3.87(s, 1H), 3.85(dd, J=6.4, 9.2Hz, 1H ), 3.58(t, J=8.4Hz, 1H), 3.52(dd, J=7.2, 9.2Hz, 1H), 3.28(s, 2H); 13 CNMR (100MHz, D 2 O): δ88.1, 85.9, 85.3, 80.9, 80.8, 80.4, 79.7, 74....

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Abstract

The invention discloses a novel carbohydrate compound and its derivative, its synthesis method and application, and particularly relates to a high-carbon carbohydrate compound and its derivative, its synthesis method and its application. The high-carbon sugar compound of the present invention has the following structure: ∴ It is prepared by the following method: dissolving 1,4:3,6-dicondensed fructose in an organic solvent, and performing an addition reaction at a certain temperature in the presence of a catalyst. Get high carbohydrates. The high-carbon sugar can be used as an ideal intermediate for the synthesis of asymmetric organic compounds and medicines, and can be used for the synthesis of chiral amino alcohols, amino sugars, oxazolines, and amides derivatives, and can also be used for the synthesis of chiral polymers. Add and reduce it with nitro compounds; or react it with diamine or amino alcohol compound; or react it with hydroxylamine and then reduce it to obtain various amino derivatives.

Description

technical field [0001] The present invention relates to sugar compounds and their preparation methods and uses, in particular to a high-carbon sugar and its derivatives and their preparation methods and uses. Background technique [0002] Sugar, protein, and nucleic acid are three important biomolecules involved in the essence of life activities. In the process of life activities, the role of sugar as an energy substance has long been known by people. With the development of molecular biology and cell biology, many other biological functions of sugars have been continuously recognized. Sugars can not only directly participate in life processes in the form of polysaccharides or free oligosaccharides, but also participate in many important life activities as sugar complexes. , so the research on glycochemistry will become one of the central research topics in life science in the future. [0003] High-carbon sugars customarily refer to derivatives of monosaccharides containing...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D493/04C07H3/00C07D307/00
Inventor 刘宏民刘丰五张雁冰戴桂馥刘振中
Owner KAIFENG PHARMA GRP
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