Alpha-arbutin intermediate, 1, 2-cis- indican derivate and stereoselective synthetic method

Abstract

The invention discloses an alpha-arbutin intermediate, a 1, 2-cis-Piceid derivative and the stereo-selectivity synthetic method thereof. Under the condition of room temperature, the invention is added with pentabenzoylglucose donator, hydroquinone or a phenol derivative and a solvent, which is added with Lewis acid slowly under the condition of continuous stirring after being cooled, heated to room temperature, kept warm at a reflow temperature, stirred and reacts; reacting mixture is separated through recrystallization or silicagel column and the alpha-arbutin intermediate or the 1, 2-cis-Piceid derivative thereof is obtained through stereo-selectivity synthesis. The invention is synthesized from pentabenzoylglucose by single stage method and glycosyl donator is easy for obtaining; reaction is carried out under mild condition and low temperature is not needed; the stereo-selectivity of glycosyl synthesis is high; a polyphenol compound does need to protect other groups thereof and attends the reaction directly, which overcomes the malady of long technique route, reduces synthesis steps and lowers production cost.

Description

technical field [0001] The invention belongs to the technology of fine chemicals and sugar chemistry, in particular a novel method for stereoselectively synthesizing α-arbutin intermediates and 1,2-cis glycoside analogues thereof. Background technique [0002] Arbutin (β-arbutin, 1) is a natural product extracted from blueberry leaves. It has a wide range of uses. It can be used as a photo color stabilizer. It has certain diuretic and antiasthmatic effects. Its excellent whitening effect (Maeda K, Fukuda M. Arbutin: Mechanism of Its Depigmenting Action in Human Melanocyte Culture [J]. J Pharmacol. Exp. Ther., 1996, 276: 765-769) has been widely used in various cosmetics. Recently, the biological activity of α-arbutin (α-arbutin, 2) has attracted people's attention again, because its IC 50 = 2.1 Much lower than the IC of β-arbutin 50 ≥30, while having a strong tyrosine oxidase inhibitory effect, it inhibits the growth of normal cells less than β-arbutin (Sugimoto K, Nishimu...

AI Technical Summary

Problems solved by technology

[0005] 1) The aromatic ring has electric absorption, which leads to weak nucleophilicity of phenols in acidic conditions, and the power supply of the hydroxyl group on the benzene ring makes the aromatic ring of phenols also have considerable nucleophilicity ( figure 2 ), which leads to the generation of carbon glycosides, so the generation of aryl glycosides is more difficult than that of aliphatic glycosides;

[0006] 2) The preparation of fully protected or partially protected compounds with no adjacent groups participating in the C-2 position usually requires multi-step reactions, and the yield is low

Pd / C is required for the removal of benzyl group, the reaction conditions are high, and the large-scale synthesis is limited

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