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Preparation method of C-aryl glucoside compound

An aryl glycoside and compound technology, which is applied in the field of preparation of C-aryl glycoside compounds, can solve the problems of cumbersome pre-functionalization operation of aryl metal species, poor regioselectivity and stereoselectivity, etc., and achieves good stereoselectivity, Post-processing green, simple operation steps

Active Publication Date: 2020-06-12
HUAQIAO UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

These methods often have limitations such as poor regioselectivity and stereoselectivity, and cumbersome prefunctionalization of aryl metal species.

Method used

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  • Preparation method of C-aryl glucoside compound
  • Preparation method of C-aryl glucoside compound
  • Preparation method of C-aryl glucoside compound

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0027] methyl

[0028] (E)-3-(2-((2R,3R,4R,5R,6R)-3,4,5-tris(benzyloxy)-6-((benzyloxy)methyl)tetrahydro-2H-pyran-2-yl ) Preparation of naphthalen-1-yl)acrylate

[0029]

[0030] Add 0.3 mmol of cesium carbonate, 0.2 mmol of (1R, 4R)-N-phenylbicyclo[2.2.1]hept-5-ene-2-carboxamide, 0.01 mmol of palladium acetate, and 0.02 mmol of tris(2-furyl)phosphine , 1-iodonaphthalene 0.1mmol, glycosyl chloride 0.15mmol, methyl acrylate 0.2mmol, and tetrahydrofuran 1mL were added to a 15mL reaction tube, filled with nitrogen repeatedly 10 times, placed in an oil bath at 100℃, and reacted for 24h; cooled to At room temperature, the reaction solution was diluted with ethyl acetate, washed three times with water, and the organic phase was washed with anhydrous Na 2 SO 4 Dry, filter, concentrate, and purify by thin layer chromatography to obtain 71.9 mg of the target product with a yield of 98%. The NMR characterization of this compound is as follows: 1 H NMR(500MHz, CDCl 3 )δ8.37(d,J=16.2Hz,1H), 8...

Embodiment 2

[0032] methyl

[0033] (E)-3-(2-methyl-6-((2R,3R,4R,5R,6R)-3,4,5-tris(benzyloxy)-6-((benzyloxy)methyl)tetrahydro-2H-pyran Preparation of -2-yl)phenyl)acrylate

[0034]

[0035] Add 0.3 mmol of cesium carbonate, 0.2 mmol of (1R, 4R)-N-phenylbicyclo[2.2.1]hept-5-ene-2-carboxamide, 0.01 mmol of palladium acetate, and 0.02 mmol of tris(2-furyl)phosphine , 2-methyl iodobenzene 0.1mmol, glycosyl chloride 0.15mmol, methyl acrylate 0.2mmol, and tetrahydrofuran 1mL were added to a 15mL reaction tube, filled with nitrogen repeatedly 10 times, placed in an oil bath at 100°C, and reacted for 24h; Cool to room temperature, dilute the reaction solution with ethyl acetate, wash three times with water, and use anhydrous Na for the organic phase 2 SO 4 Dry, filter, concentrate, and purify by thin layer chromatography to obtain 59.3 mg of the target product with a yield of 85%. The NMR characterization of this compound is as follows: 1 H NMR(500MHz, CDCl 3 )δ7.93(d,J=16.3Hz,1H), 7.42(d,J=7.8Hz,1H)...

Embodiment 3

[0037] methyl

[0038] (E)-3-(2-methoxy-6-((2R,3R,4R,5R,6R)-3,4,5-tris(benzyloxy)-6-((benzyloxy)methyl)tetrahydro-2H-pyran Preparation of -2-yl)phenyl)acrylate

[0039]

[0040] Add 0.3 mmol of cesium carbonate, 0.2 mmol of (1R, 4R)-N-phenylbicyclo[2.2.1]hept-5-ene-2-carboxamide, 0.01 mmol of palladium acetate, and 0.02 mmol of tris(2-furyl)phosphine , 2-Methoxy iodobenzene 0.1mmol, glycosyl chloride 0.15mmol, methyl acrylate 0.2mmol, and 1mL tetrahydrofuran were added to a 15mL reaction tube, filled with nitrogen repeatedly 10 times, placed in an oil bath at 100℃, and reacted for 24h ; Cool to room temperature, the reaction solution was diluted with ethyl acetate, washed three times with water, the organic phase with anhydrous Na 2 SO 4 Dry, filter, concentrate, and purify by thin layer chromatography to obtain 44.2 mg of the target product with a yield of 62%. The NMR characterization of this compound is as follows: 1 H NMR(500MHz, CDCl 3 )δ8.08(d,J=16.2Hz,1H), 7.46–7.27(m,17H)...

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Abstract

The invention discloses a C-aryl glucoside compound preparation method, which comprises: (1) sequentially adding an alkali, a co-catalyst, a palladium catalyst, a ligand, aryl halide, glycosyl chloride, a termination reagent and an organic solvent to a reaction container subjected to nitrogen purging, and carrying out a reaction for 15-30 h at a temperature of 80-120 DEG C to obtain a mixed material; (2) diluting the mixed material obtained in the step (1) with ethyl acetate, washing with water, and separating to obtain an organic phase; and (3) drying the organic phase obtained in the step (2), filtering and concentrating the organic phase, and carrying out thin-layer chromatography or column chromatography to obtain the C-aryl glycoside compound. According to the method, different aryl-substituted C-aryl glucoside compounds can be obtained, the steps are simple, the operation is safe, the stereoselectivity is good, and the C-aryl glucoside compounds which are difficult to obtain by other methods can be synthesized.

Description

Technical field [0001] The invention belongs to the technical field of organic synthesis, and specifically relates to a preparation method of a C-aryl glycoside compound. Background technique [0002] Enzyme-catalyzed glycosylation is an important means of modifying biologically active molecules in nature. In addition to the common O-glycosides and N-glycosides, C-aryl glycoside compounds are also widely present in nature and play an important role in drug design. Compounds with aryl glycosides all exhibit excellent biological activities, such as antifungal and antitumor effects. Due to the high stability of C-glycosidic bonds, carbon glycosylation is also an effective strategy for the modification of glycoconjugate-containing drugs. C-arylpyranose and furanose bonds found in anticancer drugs (thiazofurin) and antidiabetic drugs (dapagliflozin, canagliflozin, and empagliflozin) have been shown to be used in drug design It is an excellent sugar-like pharmacophore. The tradition...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D309/10C07D405/04C07D493/14C07D493/04
CPCC07D309/10C07D405/04C07D493/14C07D493/04
Inventor 程国林吕薇薇
Owner HUAQIAO UNIVERSITY
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