Synthesis method of 2-deoxysugar oxygen glycoside and application of 2-deoxysugar oxygen glycoside to pharmacy

Abstract

The invention provides a synthesis method of 2-deoxysugar oxygen glycoside. The synthesis method comprises the following steps: adding 3, 4-O-carbonate galactose glycal, a sugar receptor and a catalyst into an organic solvent, performing stirring at room temperature, detecting the reaction process by TLC, terminating the reaction when a 3, 4-O-carbonate galactose glycal raw material completely disappears, extracting and collecting an organic phase, performing reduced pressure distillation to remove the solvent to obtain a crude product, and then performing column chromatography by adopting a petroleum ether / ethyl acetate solution as a mobile phase to obtain 2-deoxyglycoside. According to the invention, compounds such as alpha-diacetone D-galactose-3, 4-O-2-deoxyglycoside and alpha-L-menthol-3, 4-O-2-deoxyglycoside show significant inhibition effects on glucosidase, and the IC50 values of the compounds on glucosidase are calculated to be 121.14 [mu] M and 54.64 [mu] M respectively;.

Description

technical field [0001] The invention relates to a synthesis method of 2-deoxyglucoside, which is applied in the field of pharmacy. Background technique [0002] Deoxysugars are the basic structural components of various biologically active natural products. Many biologically active compounds, especially antitumor antibiotics, such as anthracyclines, aureomycins, native mycins, and angucyclines, have Contains one or more 2-deoxyglycosides. As an important subclass of deoxysugars, 2-deoxyglycosides lack a directing group at C-2 to control anomeric selectivity, which makes their stereoselective synthesis challenging. Despite the difficulties, efforts have been made to develop stereoselective glycosylation methods to construct 2-deoxyglycosidic linkages. [0003] Stereoselective construction of 2-deoxysugars has been achieved by indirect and direct synthetic strategies. In indirect synthesis, a temporary directing group is usually preinstalled at C-2 to help control anomeric ...

AI Technical Summary

Problems solved by technology

However, pre-installation and removal of these temporary directing groups usually requires additional steps, resulting in reduced efficiency of indirect synthetic methods

On the other hand, the direct synthesis of 2-deoxysugars is considered more "direct" and "atom-economical" with higher synthesis efficiency, but stereoselective control is usually more challenging due to the lack of a temporary directing group at C-2

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