Method for synthesizing aminoglucose tetrasaccharide

A technology of glucosamine and a synthetic method, applied in the field of preparation of oligosaccharides, can solve problems such as complicated steps, and achieve the effects of simple steps, suitable for mass preparation, and easy operation

Inactive Publication Date: 2008-04-30
DALIAN INST OF CHEM PHYSICS CHINESE ACAD OF SCI
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0005] Disadvantages: The reported synthesis method of β1→4-linked glucosamine tetrasaccharide and hexasaccharide is relatively cumbersome, and the protecting group benzyl group is not easy to remove

Method used

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  • Method for synthesizing aminoglucose tetrasaccharide
  • Method for synthesizing aminoglucose tetrasaccharide
  • Method for synthesizing aminoglucose tetrasaccharide

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Embodiment

[0032] Below in conjunction with embodiment the present invention is described in detail:

[0033] (1) 3,4,6-tri-oxo-acetyl-2-deoxy-2-phthalimido-β-D-glucopyranose-(1→4)-6-oxo- Synthesis of tert-butyldimethylsilyl-2-deoxy-2-phthalimido-β-D-glucopyranose isopropylthioside 1

[0034] Isopropylthio β-D-glucopyranoside 8 (1.4 g, 2.9 mmol) and 1.1 equivalents of trichloroacetimidate 7 (1.62 g, 2.8 mmol) of the donor compound glucopyranose were dissolved In 15ml of dry dichloromethane, cool to -10°C in an ice-salt bath, in a nitrogen atmosphere, add 0.07 equivalent (35μl) of trimethylsilyl trifluoromethanesulfonate to catalyze the coupling reaction After reacting for half an hour, two drops of triethylamine were added to neutralize the reaction system, the solvent was distilled off under reduced pressure, purified and separated by silica gel chromatography, and 1.34 g of solid foam 1 was obtained. Acetylated 1 1 H NMR (CDCl 3 )δ: 0.08, 0.09(2s, 6H, Si(CH 3 ) 2 ), 0.93(s, 9H, t...

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Abstract

The invention relates to the preparation for oligosaccharide having biological activity, in particular to a synthetic method for amino glucose tetrose. Amino glucose diose glucoside connected through octyl-Beta-(1-4) is taken as acceptor, the amino glucose diose glucoside connected through 1-4 is taken as donator, lewis acid and iodo-succinimide are taken as catalyst, and the amino glucose tetrose is synthesized in organic solvent. The invention has the advantages that the synthetic route is simpler than a reported method, the operation is easy, the reaction is short, the reagent consumption is low, and the invention is suitable for the mass preparation. In addition, besides target tetrose, the other tetrose with an analogous structure can also be obtained simultaneously, and the active screening can be also performed.

Description

technical field [0001] The invention relates to the preparation of biologically active oligosaccharides, in particular to a simple synthesis method of glucosamine tetrasaccharide which can be used for drug screening. Background technique [0002] β1→4-linked glucosamine oligosaccharides are also called chitosan oligosaccharides, and there are many research reports on the biological activities of chitosan oligosaccharides. Studies have shown that chitosan oligosaccharides have antibacterial, anti-tumor, and various activities such as improving immunity. The materials used in the study of chitosan oligosaccharide bioactivity are generally chitosan oligosaccharide mixture obtained by degradation of chitosan, so obtaining pure chitosan oligosaccharide is the basic raw material for studying the relationship between the structure and function of chitosan oligosaccharide. [0003] Literature 1 (Mohamed R.E.Aly, El-Sayed I.Ibrahim.Carbohrdr.Res. 2001, 31, 129-142.) reported the cla...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07H5/06C07H3/06C07H1/00
Inventor 杜昱光刘红梅谭成玉杜宇国白雪芳
Owner DALIAN INST OF CHEM PHYSICS CHINESE ACAD OF SCI
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