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A kind of fructan, its intermediate, preparation method and application

A technology of fructan and its compounds, applied in the fields of fructan, its intermediates, preparation and application, can solve the problems of harsh reaction conditions, low yield, low yield of fructooligosaccharide preparation, etc.

Inactive Publication Date: 2017-07-04
SHANGHAI INST OF PHARMA IND CO LTD +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0016] The technical problem to be solved by the present invention is that, in order to overcome the defects of the low yield of the preparation method of fructopyranoside in the prior art, the scope of application is small, the reaction conditions are harsh, and the preparation yield of the oligofructose donor is low. Provide a kind of fructan, its intermediate and glycosidation donor, preparation method and application

Method used

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  • A kind of fructan, its intermediate, preparation method and application
  • A kind of fructan, its intermediate, preparation method and application
  • A kind of fructan, its intermediate, preparation method and application

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0087] The preparation of embodiment 1 raw material

[0088]

[0089] Add 30g of D-Fructose and 600ml of acetone into the reaction flask, add 3ml of concentrated sulfuric acid dropwise in the ice-water bath, react in the ice-water bath for 5h, and quench the reaction with 180ml of saturated sodium bicarbonate in the ice-water bath. The reaction solution was spin-dried, extracted with DCM, the organic phase was dried, and the solid was recrystallized from ethyl acetate / n-hexane to obtain 21.552 g.

[0090]

[0091] Add 3gX5-4 and 140ml of 0.1% HCl to the reaction bottle, TLC until the reaction is complete, quench the reaction with saturated sodium bicarbonate solution in an ice-water bath, spin the reaction solution with an oil pump, and pass through the column to obtain 2.226g of the product, with a yield of 88%.

[0092]

[0093] Add 3.016gX5-5, 30ml of dichloromethane, 6.28ml of pyridine to the reaction flask, add 6.67ml of benzoyl chloride dropwise in an ice-water ...

Embodiment 2

[0103]

[0104] Compound VI (336mg, 0.44mmol), molecular sieves (336mg) and compound V (259mg, 0.53mmol, 1.2eq) were dissolved in 8ml of dichloromethane (re-distilled), stirred at -18°C for 0.5 hours, then dropped into TMSOTf (0.005ml , 0.026mmol, 0.06eq), react at -18°C for 1.5 hours, then stir at room temperature for 1 hour (TLC detection is exhausted), add 0.1ml triethylamine to quench the reaction, filter, concentrate the organic phase, and pass through the column to obtain a white solid (461mg , yield 98%), 1 H NMR (400MHz, CDCl 3 ):δ8.15-7.14(m,35H),6.42(d,1H,J=10.0Hz),6.19(d,1H,J=10.4Hz),6.01(dd,1H,J=10.4,3.2Hz) ,5.84-5.80(m,3H),4.80(d,1H,J=11.6Hz),4.44(s,1H),4.40(d,1H,J=2.8Hz),4.29(d,1H,J=12.8 Hz), 4.08(d, 1H, J=1.6Hz), 4.05(d, 1H, J=1.6Hz), 4.02(d, 1H, J=10.4Hz), 3.85(d, 1H, J=10.8Hz) ;ESI-MS(m / z):[M+Na] + :1093.03.

Embodiment 3

[0106]

[0107] Compound II-1 (200mg, 0.187mmol), N-benzenetrifluoroacetimidoyl chloride (116mg, 0.56mmol, 3eq) was dissolved in 5ml of acetone, potassium carbonate (77mg, 0.56mmol, 3eq) was added in batches, and stirred at room temperature 1 hour (TLC detection is consumed), filtered, spin-dried the filtrate, and passed through the column to obtain a white solid (229mg, yield 99%), ESI-MS (m / z): [M+Na] + :1264.15, 1 HNMR (400MHz, CDCl 3):δ8.44-6.66(m,40H),6.49(d,1H,J=10.0Hz),6.02(dd,1H,J=8.8,3.6Hz),5.97(d,1H,J=3.6Hz) ,5.81(s,1H),5.77(dd,1H,J=10.0,2.8Hz),5.08(d,1H,J=9.2Hz),4.71(d,1H,J=12Hz),4.53-4.40(m ,4H),4.03(d,2H); 13 C NMR (100MHz, CDCl 3 ):165.95-164.80(C,C=O),143.07(C,N-C),133.42-128.00(C,Ar),124.76(C,C-F),119.13(C,Ph),106.36,99.82,70.21,69.93 ,69.54,69.13,67.85,66.90,63.86,63.00,62.18,58.84.

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Abstract

The invention discloses a fructan, and an intermediate, a preparation method and an application thereof. The preparation method of the fructan I comprises the steps: in an organic solvent, and under the action of an alkaline reagent, carrying out a deprotection reaction on a compound II to obtain the compound I, wherein n=0-14, m=5-18, and R3, R4 and Rm are the same or different acyls. The fructan has better antitumor activity, the preparation condition is mild, and the yield is relatively high.

Description

technical field [0001] The invention relates to a kind of fructan, its intermediate, preparation method and application. Background technique [0002] Fructan is a linear or branched polymer composed of fructose. Fructans in nature are important storage carbohydrates of about 15% of angiosperms, and are generally formed by the polymerization of furan-type fructose monosaccharides through β bonds. The fructosides in nature mainly appear in the furan-type form, and most of the synthetic methods are also about the furan-type fructosides, but there are few about the synthesis of pyranosides. However, some fructopyranosides have been shown to have better biological and pharmacological activities. For example, Topate (1) is the most popular anticonvulsant drug, with sales of $2.7 billion in 2008. In 2011, n-butyl β-D-fructoside (2), which was isolated from traditional Chinese medicine, was reported to have significant gastric cancer inhibitory activity. [0003] [0004] At...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07H3/04C07H3/06C07H1/00C07H13/06C07H13/02C07H13/00C08B37/00A61P35/00
Inventor 林峰卢锐徐秋龙陈建丽韩金娥
Owner SHANGHAI INST OF PHARMA IND CO LTD