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Preparation method of methoxylphenyl propanol substituted 6-amino-beta-cyclodextrin derivative

A technology of methoxyphenylpropanol and methoxyphenyl, which is applied in the field of preparation of 6-amino-β-cyclodextrin derivatives substituted by methoxyphenylpropanol, which can solve the limitations, limited water solubility, etc. question

Inactive Publication Date: 2012-12-12
SHANGHAI RUICHUANG MEDICAL TECH
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  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The limited water solubility of natural β-cyclodextrins limits its ability to form inclusion complexes with guest compounds as host compounds

Method used

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  • Preparation method of methoxylphenyl propanol substituted 6-amino-beta-cyclodextrin derivative

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Embodiment 1

[0010] 6-iodo-6-deoxy-β-cyclodextrin ( 2 ) preparation

[0011] Starting from β-cyclodextrin (1), compound 2 was synthesized according to the method of Baer HH et al. (Carbohydr. Res. 228: 307-314). The experimental yield was 92%.

[0012] 6-[1-(4-methoxyphenyl)-1-propanol)-amino-6-deoxy-β-cyclodextrin ( 3 ) preparation

[0013] Add 1-(4-methoxyphenyl)-1-propanolamine (135 mmol) to compound 2 (0.45 mmol), stir and heat to 80 o C, reacted for 48 hours. After the reaction solution was cooled to room temperature, 5 ml of methyl tert-butyl ether was added, the precipitate was filtered and washed with 10×10 ml of acetone, and dried in vacuo to obtain compound 3 as a pale yellow solid with a yield of 91%. [R] D +12°( c = 1.0 in DMF at 25 °C); LC-ESIMS m / z [M+2] 2+ / 2, [M + 3] 3+ / 3; 1 H NMRδppm (400 MHz, CD 3 SOCD 3 ) 7.06 (d, J = 7.5Hz, 14H), 6.67 (d, J = 7.5Hz, 14H), 4.90 (bd, 7H, H-1), 3.72 (m, 7H, H-5), 3.68 (m, 7H, H-3), 3.65 (m, 7H, H-2) , 3.65 ...

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Abstract

The invention provides a preparation method of a methoxylphenyl propanol substituted 6-amino substituted-beta-cyclodextrin derivative capable of forming cations. The method uses beta-cyclodextrin as a starting material and comprises three steps including 6th site iodine (bromine) substitution and an amido radical substitution reaction for respective preparation of per-6-[1-(4-methoxylphenyl)-1-propanol]-amino-6-deoxy-b-cyclodextrin and 6-[1-(3-methoxy phenyl)-1-propanol]-amino-6-deoxy-beta-cyclodextrin.

Description

technical field [0001] The present invention relates to a preparation method of 1-(4-methoxyphenyl)-1-propanol-substituted 6-amino-substituted β-cyclodextrin derivative capable of forming cations. This method uses β-cyclodextrin as the starting material to prepare 6-[1-(4-methoxyphenyl)-1- Propanol)-amino-6-deoxy-β-cyclodextrin is per-6-[1-(4-methoxylphenyl)-1-propanol]-amino-6-deoxy-β-cyclodextrin and 6-[1 -(3-methoxyphenyl)-1-propanol)-amino-6-deoxy-β-cyclodextrin per-6-[1-(3-methoxylphenyl)-1-propanol]-amino - The method of 6-deoxy-β-cyclodextrin. Background technique [0002] Cyclodextrins are a class of natural cyclic oligosaccharide compounds, the common ones are α, β and γ cyclodextrins. Among them, β-cyclodextrin is the most commonly used, which is composed of seven α-D-glucose units linked by 1,4-glycosidic bonds in a ring. Like other cyclodextrins, its molecular structure contains a hydrophilic outer surface and a hydrophobic inner cavity, which allows it to fo...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C08B37/16
Inventor 邓京振
Owner SHANGHAI RUICHUANG MEDICAL TECH
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