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Synthetic method of saponin

A technology for saponins and aglycones, which is applied in the field of construction strategies of glycosidic bonds in saponins, can solve the problems of increasing production costs, unfavorable industrial production, etc., and achieves the effects of easy operation, easy industrial production, and strong practical operability.

Inactive Publication Date: 2015-06-10
YANGZHOU BLUE BIOMEDICAL TECH CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0006] Secondly, since the glycosidation reaction in the synthesis of saponins is the reaction between the active sugar group donor and the hydroxyl group in the aglycone, the prior art requires strict control of water in the reaction system for constructing glycosidic bonds, and generally requires the use of dried Anhydrous solvents are processed, and the reaction system needs to be fed with nitrogen or inert gas, which greatly increases the cost of production and is not conducive to large-scale industrial production

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0026] 3-O-β-D-glucopyranose-dehydroepiandrosterone ( )Synthesis

[0027] Weigh dehydroepiandrosterone (34.6 g, 0.12 mol), D-glucose (18.0 g, 0.1 mol) and dissolve it in anhydrous toluene (200 mL). o Under C, add H 2 SO 4 -SiO 2 (250 mg, 0.5 mmol), react at a constant temperature under argon protection, until TLC detects that D-glucose almost completely disappears (about 5h), after concentrating the reaction, it is subjected to silica gel column chromatography (silica gel 100~200 mesh), first Methyl chloride was used as the eluent, TLC detection until there was no dehydroepiandrosterone in the eluent, the eluent was concentrated to obtain dehydroepiandrosterone (14.4g, 0.05 mol), and then ethyl acetate as the eluent The elution was continued and TLC was detected until there was no title compound in the eluate. The eluate was concentrated to obtain 22.5 g of a white solid, which was the title compound. The yield was 50.0%, and the purity by HPLC was about 98.6%.

[0028] Structural...

Embodiment 2

[0034] Trillin (CAS registration number: 14144-06-0, structural formula: )Synthesis

[0035] Weigh diosgenin (62.2 g, 0.15 mol), D-glucose (18.0 g, 0.1 mol), dissolved in THF (300 mL), and add TfOH-SiO 2 (500 mg, 1.0 mmol), the reaction was refluxed until D-glucose almost completely disappeared as detected by TLC (about 12h). After the reaction was concentrated, it was subjected to silica gel column chromatography (silica gel 200-300 mesh). Eluent, TLC detection until there is no diosgenin in the eluate, concentrate the eluate to obtain diosgenin (16.6 g, 0.04 mol), and then use ethyl acetate as the eluent to continue the elution, TLC detection until There is no trillium glycoside in the eluate. The eluate was concentrated to obtain trillium glycoside (46.1 g) with a yield of 80% and a purity of 96.5% by HPLC.

[0036] Structure confirmation data: Melting point: 275-280℃, ESI-MS(m / z): 577.5 [M+H l + , 1 HNMR(400 MHz, CD 3 OD) δ :0.64(3H, d, J=5.1Hz, CH 3 -27), 0.78(3H, s, CH 3 -18...

Embodiment 3

[0038] 3-O-β-L-arabinose-oleanolic acid benzyl ester ( )Synthesis

[0039] Weigh benzyl oleanolic acid (136.7 g, 0.25 mol), L-arabinose (15.0 g, 0.1 mol), and dissolve them in dioxane (500 mL). o Under C, add HClO 4 -SiO 2 (1.0 g, 2.0 mmol), react at a constant temperature until L-arabinose is almost completely disappeared (about 2 h) detected by TLC. After the reaction is concentrated, it is subjected to silica gel column chromatography (silica gel 200-300 mesh), first with dichloromethane Methane was used as the eluent, TLC detection until there was no benzyl oleanolic acid in the eluate, the eluate was concentrated to obtain benzyl oleanolic acid (65.6 g, 0.12 mol), and then use ethyl acetate as The eluent continued to elute, and TLC detected until there was no title compound in the eluate. The eluate was concentrated to obtain the title compound (48.9 g) with a yield of 72% and a purity of 97.3% by HPLC.

[0040] Structural confirmation data: ESI-MS(m / z): 701.5[M+Na l + , 1 H ...

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PUM

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Abstract

The invention belongs to the field of organic synthesis, and involves a synthesis method of saponin, and in particular a method to construct glycosidic bond in saponin. The method includes the following steps: directly reacting an excessive amount of aldose or ketose with aglycone in an appropriate organic solvent under the action of an acid catalyst and reflux temperature of 30 DEG C to obtain the target product of saponin.

Description

technical field [0001] The invention belongs to the field of organic synthesis and relates to a construction strategy of glycosidic bonds in saponins. Background technique [0002] Saponins are a special class of secondary metabolites, sugar moiety and triterpene, steroid or steroid alkaloid connected by glycosidic bonds conjugate. According to the structure of saponins, it can be divided into triterpenoid saponins, steroidal saponins and steroidal alkaloids. Saponin is a glycoconjugate of triterpenes and steroids that widely exists in nature and has a wide range of activities. Antibacterial, antiviral, hypoglycemic, prevent and treat cardiovascular disease, hypotensive, diuretic, anti-fatigue, antipyretic and analgesic, liver protection, etc., and can also be used as a natural food sweetener, protective agent, foaming agent, and flavor enhancer , antioxidants, etc. However, saponins always exist in a large family with similar structures in nature, which makes the separa...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07J71/00C07J63/00C07J17/00C07J75/00C07H15/256C07H1/00
CPCC07H1/00C07H15/256C07J17/005C07J63/008C07J71/0005
Inventor 陈敏其他发明人请求不公开姓名
Owner YANGZHOU BLUE BIOMEDICAL TECH CO LTD
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