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Androstanol alkyl carbonic ether compound and preparation process thereof

A technology for androstanol alkyl carbonate and compound is applied in the field of organic compound and organic compound preparation, and can solve problems such as troublesome, uneconomical, low oral activity and the like

Inactive Publication Date: 2002-10-02
台州市兴业化工厂 +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, an outstanding shortcoming of this type of compound is that the oral activity is too low. If it is taken as a health food in large doses, it is both troublesome and uneconomical.

Method used

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Examples

Experimental program
Comparison scheme
Effect test

example 2

[0018] 10g androstene corresponding compound 1-androstene-3β, 17β-diol was dissolved in 150g dichloromethane, N 2 Protect, electromagnetically stir, add 50g of triethylamine, slowly dropwise add 38g of methyl chloroformate corresponding to alkyl chloroformate, control the reaction temperature at 55-60°C, and stir for 5 hours. The reaction solution was washed 3 times with 10% hydrochloric acid, each hydrochloric acid consumption 15g; then washed with saturated NaCl aqueous solution (15g × 3), anhydrous NaCl 2 SO 4 Drying, removing the solvent under reduced pressure to obtain an oily crude product, the crude product was separated by silica gel column chromatography, the eluent was a mixture of petroleum ether and ethyl acetate, petroleum ether:ethyl acetate=10:1, and the product androstanol alkyl Carbonate corresponding compound 1-androstene-3β, 17β-diol bis(methyl carbonate) 13.47g, yield 96.2%. Example 2: One of the androstyl alkyl carbonate compounds 1-androstene-3β, 17β-di...

Embodiment 3

[0020] Except triethylamine consumption is 30g, methyl chloroformate consumption is 23g, all the other operations are with example 1, get 1-androstene-3β, 10.19g of 17β-diol bis(methyl carbonate) ester, yield 72.8%, simultaneously 1.20 g of a mixture of 1-androstene-3β, 17β-diol 3-(methyl carbonate) ester and 1-androstene-3β, 17β-diol 17-(methyl carbonate) ester were obtained. Example 3: 5α-androsterol-3β, 17β-diol bis

[0021] Preparation of (Benzyl Carbonate) Ester

[0022] 10g of the corresponding compound of androsterols 5α-androst-3β, 17β-diol was dissolved in 150g of dichloromethane, N 2 Protect, electromagnetically stir, add 50g of triethylamine, slowly dropwise add 68g of benzyl chloroformate corresponding compound of alkyl chloroformate, control the reaction temperature at 55-60°C, and stir for 5 hours. The reaction solution was washed 3 times with 10% hydrochloric acid, each hydrochloric acid consumption 15g; then washed with saturated NaCl aqueous solution (1...

Embodiment 4

[0022] 10g of the corresponding compound of androsterols 5α-androst-3β, 17β-diol was dissolved in 150g of dichloromethane, N 2 Protect, electromagnetically stir, add 50g of triethylamine, slowly dropwise add 68g of benzyl chloroformate corresponding compound of alkyl chloroformate, control the reaction temperature at 55-60°C, and stir for 5 hours. The reaction solution was washed 3 times with 10% hydrochloric acid, each hydrochloric acid consumption 15g; then washed with saturated NaCl aqueous solution (15g × 3), anhydrous NaCl 2 SO 4 Drying, removal of solvent under reduced pressure, the oily crude product was obtained, the crude product was separated by silica gel column chromatography, the eluent was a mixture of petroleum ether and ethyl acetate, petroleum ether:ethyl acetate=10:1, and the product androstanol alkyl Carbonate corresponding compound 5α-androst-3β, 17β-diol bis(benzyl carbonate) 17.64g, yield 92%. Example 4: 19-desmethylandrost-4-ene-3β, one of the androsty...

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PUM

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Abstract

The present invention uses androstalcohol correspondent compound and alkyl chloroformate correspondent compound as raw material and makes them implement further esterification in the dichloromethane solvent to obtain the invented androstalcohol alkyl carbonate correspondent compound. Said compound can be used as nutrient health-care product with the functions of reducing fat and raising hardness of muscles, its oral activity is high, and it is easy to be absorbed by intestinal tract.

Description

technical field [0001] The invention relates to new organic compounds of androstanyl alkyl carbonates and a preparation method thereof, belonging to the technical field of organic compounds and organic compound preparation. The structural formula of this type of organic compound is: (1) R=R'=CH 3 OCOO-,n-C 3 h 7 OCOO-, i-C 3 h 7 OCOO-,n-C 4 h 9 OCOO-, i-C 4 h 9 OCOO-,t-C 4 h 9 OCOO-, PhCH 2 OCOO-, (2) R≠R', R=CH 3 OCOO-,n-C 3 h 7 OCOO-, i-C 3 h 7 OCOO-,n-C 4 h 9 OCOO-, i-C 4 h 9 OC(O)O-, t-C 4 h 9 OC(O)O-, PhCH 2 OC(O)O-, R'=HO-,=O(3)R≠R', R'=CH 3 OCOO-,n-C 3 h 7 OCOO-, i-C 3 h 7 OCOO-,n-C 4 h 9 OCOO-, i-C 4 h 9 OCOO-,t-C 4 h 9 OCOO-, PhCH 2 OCOO-, R=HO-,=O Background technique [0002] 1-androstenediol, 4-androstenediol, 5-androstenediol, 19-desmethyl-4-androstenediol, 5α-androstenediol and other androstene are a class of Prosteroid (steroid Precursor) compounds have good protein assimilation, and the na...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07J3/00C07J9/00
Inventor 潘朝阳汤杰蒋胜力杨帆陈建华洪镛裕
Owner 台州市兴业化工厂