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Glycosyl polyethers, preparation method thereof and use thereof

A technology of sugar base and synthesis method, which is applied in the preparation of sugar derivatives, chemical instruments and methods, sugar derivatives, etc., can solve problems such as limited synthesis methods, and achieve the effects of easy availability of raw materials, easy control of conditions, and simple methods.

Inactive Publication Date: 2012-08-29
SHANGHAI INST OF ORGANIC CHEM CHINESE ACAD OF SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

So far, due to limited synthetic means, the simulation of glycoconjugates is limited to linking some shorter aliphatic chains or aliphatic chains on the sugar base [(a) A.Geyer, C.Gege, R.R.Schmidt, Angew. Chem.Int.Ed.1999, 38, 1466-1468.(b) S.R.Haseley, H.J.Vermeer, J.P.Kamerling, J.F.G.Vliegenthart, Proc.Natl.Sci.USA2001, 96, 9419-9424], while for some longer Fatty chains or fatty chains are rarely reported [K.Matsuura, H.Kitakouji, N.Sawada, H.Ishida, M.Kiso, K.Kitajima, K.Kobayashi, J.Am.Chem.Soc.2000, 122 , 7406-7407.]

Method used

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  • Glycosyl polyethers, preparation method thereof and use thereof
  • Glycosyl polyethers, preparation method thereof and use thereof
  • Glycosyl polyethers, preparation method thereof and use thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0049] Will help to understand the present invention by following example, but content of the present invention can not be limited:

[0050]

[0051] Compound 1 (142 mg, 0.30 mmol) was dissolved in 30 mL of dry tetrahydrofuran, TMSOTf (14 uL, 0.06 mmol) was added, stirred at room temperature for 15 min, and then poured into ice water to obtain a white suspension, which was filtered and dried to obtain a white solid 2 (THF conv: 4.7%). 1 H NMR (400MHz, CDCl 3 ): δ5.48(dd, 0.55H, J=10.0, 0.8Hz, H4α), 5.09-4.95(m, 2H, H1α, H3α, H4β, H3β), 4.39(d, 0.46H, J=8.0Hz, H1β), 4.29(dd, 1H, J=12.4, 4.4Hz, H6β, H6α), 4.15-4.00(m, 1.85H, H6β', H5α, H6α'), 3.41(m, 390H,), 2.05-1.99 (m, 9H, Ac), 1.62(m, 390H). 13 C NMR (75MHz, CDCl 3 ): δ170.4, 169.9, 169.6, 102.0, 97.8, 71.4, 70.7, 70.5, 68.8, 68.5, 67.9, 67.5, 63.7, 62.5, 61.8, 60.8, 26.5, 20.6.

[0052]

Embodiment 2

[0054]

[0055] Compound 3 (197 mg, 0.30 mmol) was dissolved in 30 mL of dry tetrahydrofuran, AgOTf (85 mg, 0.33 mmol) was added, stirred at room temperature for 9 minutes, and then poured into ice water to obtain a white suspension, which was filtered and dried to obtain a white solid 4 (THF conv: 4.6%). 1 H NMR (400MHz, CDCl 3): δ8.03-7.80(m, 8H), 7.59-7.25(m, 12H), 5.90(t, 1H, J=9.6Hz), 5.68(t, 1H, J=9.6Hz), 5.52(t, 1H, J=8.0Hz), 4.65(dd, 1H, J=12.4, 2.8Hz), 4.51(dd, 1H, J=12.0, 5.2Hz), 4.16(m, 1H), 3.41(m, 700H,) , 1.63(m, 700H). 13 C NMR (75MHz, CDCl 3 ): δ166.1, 165.8, 165.0, 133.4, 133.1, 133.1, 129.9, 129.8, 129.7(2C), 128.8, 128.4, 128.3(2C), 101.2, 72.9, 72.2, 71.9, 70.8(2C), 70.6, 70.4 (2C), 70.2, 70.1, 70.0, 69.8, 63.2, 62.7, 26.9, 26.7, 26.5, 26.3, 26.2, 26.0.

[0056]

Embodiment 3

[0058]

[0059] Compound 5 (167 mg, 0.30 mmol) was dissolved in 30 mL of dry tetrahydrofuran, 2,6-di-tert-butyl-4-methylpyridine (DTBMP) (123 mg, 0.60 mmol) was added, stirred at room temperature for 5 min, and AgPF was added 6 (113mg, 0.45mmol), stirred at room temperature for 15min and then poured into ice water to obtain a white suspension, which was filtered and dried to obtain a white solid 6 (THF conv: 6.6%). 1 H NMR (400MHz, CDCl 3 ): δ8.00(d, 2H, J=7.6Hz), 7.59-7.05(m, 18H), 5.25(t, 1H, J=8.0Hz), 4.83-4.70(m, 2H), 4.69-4.45( m, 5H), 3.90-3.70(m, 5H), 3.40(m, ~1092H,), 1.62(m, ~1092H). 13 CNMR (75MHz, CDCl 3 ): δ165.1, 138.1, 137.9, 137.8, 134.2, 134.0, 132.9, 132.0, 130.0, 129.7, 129.3, 129.1, 128.4, 128.3(2C), 128.2, 128.0, 127.8, 127.7, 127.6, 1208. ,75.2,75.0,73.8,73.5,71.4,70.7,70.6,70.4,70.1,69.7,69.4,68.8,67.4,62.6,30.2,29.6,27.3,26.8,26.6,26.5,26.3,26.0.

[0060]

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Abstract

The invention provides glycosyl polyethers, a preparation method thereof and use thereof. In the method, macromolecular glycosyl polyethers which have a molecular weight ranging from several hundred to more than 100,000 and have a structure below are prepared by starting from common glycosyl donors and by a method of using the glycosyls as starting ends, bonding the glycosyls with the open-loop long chains of alkylene oxide at anomeric positions and using common nucleopilic reagents such as hydroxys, alkoxys, aminos, nitrines and halogen atoms as capping ends. As the mechanical performance and plasticity of the glycosyl polyether compounds can be controlled conveniently by regulating the length of the polyether chain, the glycosyl polyether compounds can be used as medical materials, important materials for synthesizing polyurethane, thermoplastic polyester-polyamide elastic materials and precursors for preparing glyconanoparticles.

Description

technical field [0001] The present invention relates to the preparation method, product and application of glycosyl polyether induced by glycosyl oxygen ions. technical background [0002] Polytetramethylene glycol (PTMEG) prepared by cationic ring-opening polymerization of cyclic ethers such as tetrahydrofuran (THF) is an important raw material for the synthesis of polyurethane and thermoplastic polyester polyamide elastic materials. Compared with elastic materials produced by other materials as blocks, elastic materials made of PTMEG have excellent hydrolytic stability, air permeability and wear resistance, and also have good elasticity, flexibility and impact resistance at low temperatures It has unique and broad application prospects in textiles, pipes, chemicals and medical equipment. And polypropylene oxide is widely used in aspects such as polyurethane industry and surfactant [(a) Liu Zhihao, Sun Jingwu, polytetrahydrofuran synthetic catalyst research progress, 1999,...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C08G65/28C08G65/30C07H15/04C07H15/08C07H1/00A61K47/34
Inventor 俞飚李瑶
Owner SHANGHAI INST OF ORGANIC CHEM CHINESE ACAD OF SCI
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