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Beta-cyclodextrin derivative and preparation method and application thereof

A technology of cyclodextrin and derivatives, which is applied in the field of β-cyclodextrin derivatives and its preparation, can solve the problems of limited application and achieve the effects of complete series, high ee% value and easy recycling

Inactive Publication Date: 2012-08-08
SUN YAT SEN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

At the same time, cyclodextrin is only soluble in water and a few strong polar organic solvents, which limits its application in organic solvents (Chem. Rev.2003, 103, 4147 )

Method used

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  • Beta-cyclodextrin derivative and preparation method and application thereof
  • Beta-cyclodextrin derivative and preparation method and application thereof
  • Beta-cyclodextrin derivative and preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0030] In a 100mL eggplant-shaped reaction flask, 6.4459g (5.0mmol) mono(6- O - p -tosyl)- β - Cyclodextrin was dissolved in 22.9050 g (375 mmol) ethanolamine, and stirred and reacted at 120° C. for 12.0 h. Cool to room temperature, add 20 mL of water to dilute, and inject the resulting reaction mixture into 400 mL of V 乙醇 :V 丙酮 = 1:1 mixed solution, a large amount of white solids precipitated, stood still, filtered with suction, and recrystallized the obtained solids in 10mL of water. The obtained crystals were vacuum-dried at 120°C for 12.0 hours to obtain 3.6875 g of white crystals with a purity of 96.09% and a yield of 60.15%.

[0031] CD-1: [α]25 D= +150.54° ( c = 0.8020, H 2 O); m.p. > 250°C (decomp); 1 H NMR (400MHz, D 2 O): δ = 5.11-5.09 (dd, J = 6.9, 3.4Hz , 7H), 4.02-3.88 (m, 26H), 3.76-3.58 (m, 14H), 3.49-3.44 (m, 1H), 3.12-3.09 (m, 1H), 2.90-2.75ppm ( m, 4H); 13 C NMR (400MHz, D 2 O): δMS (ESI): m / z : 1200.5 [ M +Na] + , 1178.4 [ M +H] + ....

Embodiment 2

[0033] In a 100mL eggplant-shaped reaction flask, 6.4459g (5.0mmol) mono(6- O - p -tosyl)- β - Cyclodextrin was dissolved in 39.4275g (375mmol) of diethanolamine, stirred and reacted at 120°C for 12.0h. Cool to room temperature, add 20 mL of water to dilute, and inject the resulting reaction mixture into 400 mL of V 乙醇 :V 丙酮 = 1:1 mixed solution, a large amount of white solids precipitated, stood still, filtered with suction, and recrystallized the obtained solids in 10mL of water. The obtained crystals were vacuum-dried at 120°C for 12.0 hours to obtain 2.6862 g of white crystals with a purity of 97.08% and a yield of 42.68%.

[0034] CD-2: [α]25 D= +140.90° ( c = 0.8060, H 2 O); m.p. > 260°C (decomp); 1 H NMR (400MHz, D 2 O): δ = 5.15-5.06 (m, 7H), 4.04-3.87 (m, 26H), 3.74-3.58 (m, 14H), 3.42 (t, J = 9.3Hz, 1H), 3.09-3.05 (m, 1H), 2.86-2.69ppm (m, 8H); 13 C NMR (400MHz, D 2 O): δ = 101.78, 100.95, 83.42, 81.11-80.87 (m), 80.27, 73.19-72.75 (m), 72.10-71.6...

Embodiment 3

[0036] In a 100mL eggplant-shaped reaction flask, 6.4459g (5.0mmol) mono(6- O - p -tosyl)- β - Cyclodextrin was dissolved in 28.1663g (375mmol) of isopropanolamine, stirred and reacted at 120°C for 12.0h. Cool to room temperature, add 20 mL of water to dilute, and inject the resulting reaction mixture into 400 mL of V 乙醇 :V 丙酮 = 1:1 mixed solution, a large amount of white solids precipitated, stood still, filtered with suction, and recrystallized the obtained solids in 10mL of water. The obtained crystals were vacuum-dried at 120° C. for 12.0 h to obtain 3.1365 g of white crystals with a purity of 95.41% and a yield of 50.21%.

[0037] CD-3: [α]25 D= +147.81° ( c = 0.4860, H 2 O); m.p. > 250°C (decomp); 1 H NMR (400MHz, D 2 O): δ = 5.09 (t, J = 3.6Hz, 7H), 4.02-3.88 (m, 26H), 3.69-3.58 (m, 14H), 3.46 (t, J = 9.4Hz, 1H), 3.14-3.06 (m, 1H), 2.89-2.77 (m, 1H), 2.67-2.55 (m, 2H), 1.21-1.17ppm (m, 3H); 13 C NMR (400MHz, D 2 O): δ = 101.85, 100.34, 83.58, 81.2...

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Abstract

The invention discloses a beta-cyclodextrin derivative and a preparation method and application thereof. The beta-cyclodextrin derivative is a single [6-(2-hydroxy ethyl) amino-6-desoxy]-beta-cyclodextrin, single [6-di(2-hydroxy ethyl) amino-6-desoxy]-beta-cyclodextrin, single [6-(2-hydroxy propyl) amino-6-desoxy]-beta-cyclodextrin, single [ 6 di(2-hydroxy propyl ) amino-6- desoxy]-beta-cyclodextrin, single [6-(3-hydroxy propyl) amino-6-desoxy)-beta-cyclodextrin, single [6-methyl ( 2-hydroxy ethyl ) amino-6-desoxy]-beta-cyclodextrin, single {6- [(2S)-2-hydroxy propyl] amino-6-desoxy}-beta-cyclodextrin and single {6[(2R)-2-hydroxy propyl] amino-6- desoxy}-beta- yclodextrin. The beta-cyclodextrin derivative can be prepared by a nucleophilic substitution reaction of single (6-O-p-toluene sulfonyl)-beta-cyclodextrin and corresponding aminoalcohol. The synthesis method has the advantages of simple operation, mild reaction conditions, simple purification, high yield and good purity of object products. The beta-cyclodextrin derivative can be used as a water-soluble ligand of metal mimic enzyme in aqueous metallic catalytic oxidation and aqueous metallic catalytic reduction reaction.

Description

[0001] technical field [0002] The invention relates to the field of catalytic organic synthesis, in particular to a β - Cyclodextrin derivatives and their preparation and use. Background technique [0003] Cyclodextrin (cyclodextrin, referred to as CD) is made of D -(+)-Glucopyranose unit through α The cyclic oligosaccharides connected by -1,4-glycosidic bonds are in the shape of a truncated cone and have a special structure and property of "hydrophobic in the inner cavity and hydrophilic in the outer wall". There is only one functional group of hydroxyl in its molecule, and intramolecular hydrogen bonds are easy to form between hydroxyl groups, so the molecular structure of cyclodextrin has strong rigidity. When interacting with guest molecules with various shapes and functional groups, cyclodextrin’s It is difficult for the structure to undergo corresponding topological changes. At the same time, cyclodextrin is only soluble in water and a small number of strong pola...

Claims

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Application Information

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IPC IPC(8): C08B37/16C07B53/00
Inventor 纪红兵沈海民
Owner SUN YAT SEN UNIV
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