Synthetic method of glycopeptide
A synthesis method and glycopeptide technology, which is applied in the field of glycopeptide synthesis, can solve the problems of small loading capacity of solid phase carriers, limit the large-scale synthesis of glycopeptides, and low activity, and achieve large-scale synthesis, heterogeneous separation, and high reaction efficiency. high effect
- Summary
- Abstract
- Description
- Claims
- Application Information
AI Technical Summary
Problems solved by technology
Method used
Image
Examples
Example Embodiment
[0040] Example 1. Synthesis of ionic liquid
[0041] The reaction equation is as follows:
[0042]
[0043] Synthesis of compound 1: under the protection of nitrogen, 4-hydroxymethylphenol (4.00 g, 32.22 mmol), potassium carbonate (4.67 g, 33.82 mmol) and 1,3-dibromopropane (9.85 ml, 96.44 mmol) ) Stir and reflux in dry acetone (30 ml) for 5 hours. After TLC showed that 4-hydroxymethylphenol was consumed, the reaction solution was filtered and the solvent was evaporated under reduced pressure. The resulting mixture was separated and purified by column chromatography (ethyl acetate: petroleum ether=1:3→1:2) , Compound 1 (3.28 g, 39.6%) was obtained as a white solid.
[0044] The characterization results of compound 1 are as follows: 1 H NMR(500MHz, CDCl 3 )δ7.29(d,J=8.5Hz,2H),6.90(d,J=8.5Hz,2H),4.62(s,2H),4.11(t,2H),3.61(t,2H),2.32( m,2H); 13 C NMR(150MHz, CDCl 3 )δ158.4, 133.5, 128.7, 114.7, 65.5, 65.0, 32.4, 30.1.
[0045] Synthesis of ionic liquid represented by formula I: under ...
Example Embodiment
[0047] Example 2. Synthesis of Glycosylated Amino Acid Building Unit Formula III
[0048] The reaction equation is as follows:
[0049]
[0050] In the above reaction equation, the meanings of the abbreviations used are as follows: Troc: 2,2,2-trichloroethoxycarbonyl; TBSCl: tert-butyldimethylsilyl chloride; TBS: tert-butyldimethylsilyl; Ac : Acetyl; Fmoc: 9-Fluorenylmethoxycarbonyl; Ser: Serine; Allyl: Allyl; DMF: N,N-Dimethylformamide; DCM: Dichloromethane; DBU: 1,8-diazepine Dicycloundec-7-ene.
[0051] "One-pot method" synthesis of glycosyl donor 3: Compound 2 (12.0 g, 33.84 mmol) was dissolved in pyridine (150 ml) solvent, stirred and cooled to 0°C, and tert-butyldimethylchlorosilane (6.63 G, 44.00 mmol) was added to the reaction system, 30 minutes later, stirred overnight at room temperature. After TLC showed that compound 5 was consumed, acetic anhydride (35 ml) was added to the reaction system, stirred at room temperature for 6 hours, and the solvent was evaporated under r...
Example Embodiment
[0057] Example 3. Synthesis of glycopeptide of formula II
[0058]
[0059] In the above process, the reaction conditions of each step are as follows: (a) 1-ethyl-(3-dimethylaminopropyl)carbodiimide hydrochloride (EDCI), 4-dimethylaminopyridine (DMAP), Acetonitrile, nitrogen, room temperature, 7 hours; (b) piperidine, dichloromethane, room temperature, 0.5 hours; (c) benzotriazole-N,N,N',N'-tetramethylurea hexafluorophosphate Salt (HBTU), 1-hydroxybenzotriazole (HOBt), N,N-diisopropylethylamine (DIPEA), acetonitrile, nitrogen, room temperature, 8 hours; (d) trifluoroacetic acid: water = 95: 5 (v / v), dichloromethane, 1 hour.
[0060] In the following preparation, the heterogeneous separation method used is as follows:
[0061] Used to purify compounds supported by ionic liquids. The specific operation process is as follows: dissolve the resulting mixture in dichloromethane (10 ml / g), add 4 times the volume of isopropyl ether, and then use a rotary evaporator to remove the solvent u...
PUM
Abstract
Description
Claims
Application Information
- R&D Engineer
- R&D Manager
- IP Professional
- Industry Leading Data Capabilities
- Powerful AI technology
- Patent DNA Extraction
Browse by: Latest US Patents, China's latest patents, Technical Efficacy Thesaurus, Application Domain, Technology Topic.
© 2024 PatSnap. All rights reserved.Legal|Privacy policy|Modern Slavery Act Transparency Statement|Sitemap