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2,3-unsaturated galactopyranoside compound and synthesis method thereof

A synthesis method and compound technology are applied in the field of synthesis of 2,3-unsaturated galactosinolate compounds and can solve the problem of low selectivity and the like

Active Publication Date: 2020-02-11
CHINA THREE GORGES UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

In 2015, Sudhir Kashyap synthesized a series of sulfoglycosides by Ferrier reaction catalyzed by ruthenium trichloride reagent, but the reaction required heating, and the stereoselectivity was dominated by the α configuration produced by the anomeric effect, and the selectivity was not high.

Method used

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  • 2,3-unsaturated galactopyranoside compound and synthesis method thereof
  • 2,3-unsaturated galactopyranoside compound and synthesis method thereof
  • 2,3-unsaturated galactopyranoside compound and synthesis method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0027] Taking galactenose as an example, in the optimization experiments using different catalysts and ligands, the yield varies greatly, as follows:

[0028]

[0029]

[0030] All tests adopt 0.1mmol galactenose and 0.2mmol p-cresol, 5mol% Pd catalyst, 20mol% phosphine ligand in 2mL solvent, stirring reaction at room temperature; separation yield; =30:1.

[0031] Reaction conditions screening tests show that no ligand or catalyst reaction can be carried out (entries 1-2), using Pd2(dba)3 catalyst, Xantphos ligand in DMF, DMSO, toluene, acetonitrile, carbon tetrachloride and other solvents are all No reaction (entries 2-7), when DCM was used as solvent, there was 67% of the target reaction product (entry 8). We then proceeded to screen different catalysts (entries 9-13) to find that Pd 2 (dba) 3 It is still the optimal catalyst, and then screened different ligand types and temperatures (entries 14-22), and determined the optimal condition as (entry 20), with Pd2(dba)3...

Embodiment 2

[0035] Embodiment 2: the synthesis of compound 3

[0036] Tris(dibenzylideneacetone)dipalladium (Pd 2 (dba) 3 , 2.3mg, 0.0025mmol), 4,5-bis(diphenylphosphine)-9,9-dimethylxanthene (Xantphos, 5.8mg, 0.0010mmol) and 3,4-O-carbonate hemi-emulsion Glucose 1 (0.1 mmol) was added to 2 mL of dichloromethane and methyl thioglycolate (0.2 mmol). Stir at room temperature, TLC detects the reaction process, when the vinyl sugar raw material completely disappears, terminate the reaction, extract and collect the organic phase, distill off the solvent under reduced pressure to obtain the crude product, and then use petroleum ether / ethyl acetate solution as the mobile phase for column chromatography to obtain 4-Hydroxy-2,3-unsaturated glucosinolate 3 (91% yield).

Embodiment 3

[0037]Embodiment 3: the synthesis of compound 4

[0038] Tris(dibenzylideneacetone)dipalladium (Pd 2 (dba) 3 , 2.3mg, 0.0025mmol), 4,5-bis(diphenylphosphine)-9,9-dimethylxanthene (Xantphos, 5.8mg, 0.0010mmol) and 3,4-O-carbonate hemi-emulsion Glycol 1 (0.1 mmol) was added to 2 mL of dichloromethane and ethyl thioglycolate (0.2 mmol). Stir at room temperature, TLC detects the reaction process, when the vinyl sugar raw material completely disappears, terminate the reaction, extract and collect the organic phase, distill off the solvent under reduced pressure to obtain the crude product, and then use petroleum ether / ethyl acetate solution as the mobile phase for column chromatography to obtain 4-Hydroxy-2,3-unsaturated glucosinolate 4 (95% yield).

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Abstract

The invention provides a 2,3-unsaturated galactopyranoside compound. The structural formula of the compound is shown in the specification, wherein R1 comprises any one of methylene carboxylate, benzyl, alkyl, phenyl, substituted phenyl and a five-membered or six-membered heterocyclic group, and the five-membered or six-membered heterocyclic group comprises 2-pyrimidinyl, 2-benzoxazole or imidazolyl; and R2 comprises any one of a silicon group, C1-C18 alkyl, benzyl, phenyl, triphenylmethyl, pyridyl, benzoate, pyridine acid ester and quinolinecarboxylic acid ester. A preparation method of the compound comprises the following steps: adding a catalyst, a ligand and galactulose into an organic solvent and a sugar acceptor, carrying out stirring reaction at room temperature, carrying out TLC detection on the reaction process, and terminating the reaction after the galactulose raw material completely disappears to obtain the 2,3-unsaturated galactopyranoside. The prepared 2,3-unsaturated galactopyranoside compound is applied to the preparation of drugs for resisting gastric cancer and breast cancer, and a remarkable effect is achieved.

Description

technical field [0001] The invention mainly relates to a method for synthesizing 2,3-unsaturated galactose glucosinolates. Background technique [0002] Sulforaphane is a key mediator of cell surface recognition, cell-cell interaction and signal transduction and other life activities. More importantly, monosaccharide glucosinolates with sulfhydryl (-SH) and arylthio (-SAr) groups have been widely used in the chemical synthesis of sugars and are a common class of glycosylation reaction donors. Plays an important role in the assembly of polysaccharides and glycoconjugates. In addition, some glucosinolate compounds have been developed as drugs and used clinically, such as Afrostyraxthioside A, which is derived from a tree Afrostyraxlepidophyllus Mildbr in Africa. The natural product of seeds has good antiparasitic pharmacological activity. Therefore, it is of great significance to develop methods for synthesizing efficient glucosinolate compounds. [0003] The traditional m...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07H23/00C07H1/00A61K31/7064A61K31/7056A61K31/704A61K31/7034A61K31/7028A61P35/00
CPCC07H23/00C07H1/00A61P35/00
Inventor 姚辉黄年玉刘钥鑫郭志勇邓张双张雪晴邹坤汪鋆植贺海波
Owner CHINA THREE GORGES UNIV
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