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A kind of fluoroglycoside derivative and its preparation method

A technology of fluorinated glycosides and derivatives, which is applied in the field of synthesis of carbohydrate heterocyclic compounds, can solve the problems of harsh reaction conditions, expensive fluorinated reagents, and low fluorinated efficiency, and achieves simple methods, simple post-treatment process, and fluorinated high effect

Active Publication Date: 2018-08-17
JIANGXI NORMAL UNIV
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0007] In view of the existing defects such as high side reactions, expensive fluorinated reagents, poor stability, low fluorinated efficiency, and harsh reaction conditions in the existing fluoroglycoside preparation method, another object of the present invention is to provide a method with simple operation and low reaction conditions. Method for preparing the fluoroglycoside derivatives with mildness, low cost, few by-products and high yield

Method used

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  • A kind of fluoroglycoside derivative and its preparation method
  • A kind of fluoroglycoside derivative and its preparation method
  • A kind of fluoroglycoside derivative and its preparation method

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Experimental program
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Embodiment 1

[0035]

[0036] First refer to the literature [Veleti, S.K.; et al.J.Org.Chem, 2014, 79, 9444-9450; Wang, Yuan et al.Org.Lett, 2005, 7, 5577-5579; Kulkarni, S.S.; et al. J.Org.Chem, 2005,70,2808-2811.] Use whole acetylglucose as raw material to synthesize inner ether sugar (1a) through five-step reaction, and then TBAF·3H 2 O (1.26g, 4mmol, 2eq), KHF 2 (156mg, 2mmol, 1eq), the shrinkage endosaccharide compound 1a (712mg, 2mmol, 1equiv) was added to the reactor under the condition of isolated air; then the reactor was put into an oil bath and reacted at 70°C for 2h; after the reaction , the reaction solution was cooled to room temperature, diluted with ethyl acetate (50 mL), and washed with saturated sodium bicarbonate (10 mL) and water (5 mL). The organic layer was dried over anhydrous sodium sulfate, filtered, and the filtrate was distilled under reduced pressure and separated by silica gel flash column chromatography to obtain a single fluorinated product 1 (624 mg, 1.66...

Embodiment 2

[0048]

[0049] References [Yun, H.C.; Synthetic Communications, 2003, 33, 2349-2363; Anker, D.; Giudicelli, M.B.; Journal of Carbohydrate Chemistry, 1991, 10, 1991.]. As a raw material, the inner ether sugar (2a) is synthesized through a five-step reaction, and then TBAF·3H 2 O (1.26g, 4mmol, 2eq), KHF 2 (156mg, 2mmol, 1eq), and the shrinkage endosaccharide compound 2a (472mg, 2mmol, 1equiv) were added to the reaction kettle under the condition of isolated air; then the reaction kettle was put into an oil bath and reacted at 110°C for 3h; after the reaction , the reaction solution was cooled to room temperature, diluted with ethyl acetate (80 mL), and washed with saturated sodium bicarbonate (20 mL) and water (10 mL). The organic layer was dried over anhydrous sodium sulfate, filtered, and the filtrate was distilled under reduced pressure and separated by silica gel flash column chromatography to obtain a single fluorinated product 2 (417mg, 1.63mmol).

[0050]

[005...

Embodiment 3

[0053]

[0054] References [Coppola, Y.; Lorenzo, D.N.; J. Org. Chem. 2007, 72, 9679-9689; Wang, H.; She, J.; Zhang, L.-H.; Ye, X.-S.J. Org.Chem.2004,69,5774-5777.]. Using methyl-α-D-glucoside as raw material, the inner ether sugar (3a) was synthesized through four-step reaction, and then TBAF·3H 2 O (1.58g, 2mmol, 2eq), KHF 2 (156mg, 2mmol, 1eq), the shrinkage endosaccharide compound 3a (528mg, 2mmol, 1equiv) was added to the reaction kettle under the condition of isolated air; then the reaction kettle was put into an oil bath and reacted at 130°C for 2h; after the reaction , the reaction solution was cooled to room temperature, diluted with ethyl acetate (80 mL), and washed with saturated sodium bicarbonate (20 mL) and water (10 mL). The organic layer was dried over anhydrous sodium sulfate, filtered, and the filtrate was distilled under reduced pressure and separated by silica gel flash column chromatography to obtain a single fluorinated product 3 (477mg, 1.68mmol).

...

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Abstract

The invention discloses a fluorinated glycoside derivative and a preparation method thereof. The fluoroglycoside derivative uses a shrinkage lactose sugar compound as a substrate, and under the action of a tetraalkylammonium fluoride / potassium bifluoride composite fluorinating agent, The intramolecular nucleophilic substitution reaction is carried out to obtain the obtained product; the method is simple in operation, mild in reaction conditions, low in cost, less by-products and high in yield, and meets the requirements of industrial production.

Description

technical field [0001] The invention relates to a fluoroglycoside derivative and a method for efficiently synthesizing the fluoroglycoside derivative, belonging to the field of synthesis of carbohydrate heterocyclic compounds. Background technique [0002] In recent years, the research on fluorine-containing drugs has achieved remarkable success. Based on the special effects of fluorine, the introduction of fluorine in drug design has become an important means of modification in sugar drugs. In fluorinated sugar, since fluorine replaces the hydroxyl group on the sugar, although C-F and C-OH are similar in bond length and polarity, they change the nature of the hydrogen bond, which is manifested in the interaction of enzymes and antibodies. different binding abilities. The chemical and biochemical properties of fluorosaccharides have made them important drugs in antitumor, antiviral and tumor diagnosis. At present, a number of fluorosaccharide drugs for disease detection o...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07H15/18C07H15/04C07H15/14C07H15/203C07H1/00
CPCC07H15/04C07H15/14C07H15/18C07H15/203
Inventor 严楠廖维林胡祥国刘德永雷志伟郭晓红熊斌
Owner JIANGXI NORMAL UNIV
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