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/-Borneol-alpha-D-glucopyranoside

A synthetic method and technology of borneoside, which is applied in the field of synthesis of borneoside, can solve the problems of no literature report, excess, heavy workload and other problems in the synthesis of borneoside

Inactive Publication Date: 2015-08-26
CHIATAI QINGCHUNBAO PHARMA
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

Extracting borneoside from plants, even with the highest content of thyme leaves, at least 200kg of medicinal materials are required to obtain 10g of borneoside, the workload is very large and exceeds the requirements of laboratory equipment, and the The synthesis of glycosides does not have bibliographical information, so be badly in need of a kind of fast at present, easy, the higher synthetic method of borneoside

Method used

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  • /-Borneol-alpha-D-glucopyranoside

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0015] 1) Synthesis of compound III

[0016] Under the protection of argon, add 4.0 grams of (-)-Borneol, 2 grams of acetyl bromide-α-D-glucose, and an appropriate amount of anhydrous calcium chloride into dry dichloromethane, stir for 5 minutes, and then add 14 grams of silver carbonate , protected from light and stirred for 24 hours. The reaction solution was filtered, concentrated, and crudely separated by silica gel column chromatography to obtain the compound III The crude product, recrystallized with petroleum ether to obtain the compound of white needle crystal III , the yield is 24.0%.

[0017] 2) Synthesis of borneoside

[0018] Under the protection of argon, 3 g of compound III was dissolved in anhydrous methanol, and 6.2 mL of freshly prepared 1M sodium methoxide solution was added. After the completion of the reaction was monitored by thin-layer chromatography, it was filtered, concentrated, and separated by reverse-phase column chromatography. After elution,...

Embodiment 2

[0020] The method of this embodiment is the same as in Example 1, except that the charging amount of Compound II in Reaction 1 becomes 12.0g, and the final yield of Reaction 1 is 56.2%.

Embodiment 3

[0022] The method of this example is the same as that of Example 1, except that the amount of compound II in reaction 1 is changed to 32.0 g, and the final yield of reaction 1 is 52.1%.

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Abstract

The invention relates to a synthesis method for an important active ingredient / -borneol-alpha-D-glucopyranoside of an herb ophiopogon japonicas, wherein the synthesis method comprises two steps such as an addition reaction and a decarboxylation protection reaction. According to the present invention, borneol and D-glucose are adopted as the starting raw materials and the simple two-step reaction is performed to successfully synthesize the / -borneol-alpha-D-glucopyranoside, and the technical difficulties of raw material refining, low reaction yield, and the like are successfully overcome.

Description

technical field [0001] The invention relates to a method for synthesizing an important active ingredient of radix radix radix radix glycoside (dextroborneol glucoside). Background technique [0002] Borneoside (dextroborneol glucoside) is the main medicinal material in Shenmai injection - an important active ingredient of Ophiopogon japonicus, which can protect cardiomyocyte apoptosis, promote myocardial endothelial NO release and resist low-density lipoproteinase oxidation and other effects, the inventor’s previous research also showed that borneoside can significantly inhibit myocardial cell apoptosis caused by ischemia / reperfusion (I / R), and has a concentration-dependent effect, and has a strong effect of promoting NO release and Strong antioxidant effect, is one of the main cardiovascular active ingredients in Ophiopogon japonicus. The Ophiopogon japonicus medicinal materials selected for Shenmai injection that are currently on the market are from different origins, mai...

Claims

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Application Information

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IPC IPC(8): C07H15/203C07H1/00
CPCC07H15/203C07H1/00
Inventor 凌益平陈莉谭昌恒骆宏丰曲世津骆雅琴徐玲杰
Owner CHIATAI QINGCHUNBAO PHARMA
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